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1. Compound ID: 2386
Structure type: oligomer
; 583.5
Contained glycoepitopes: IEDB_130701,IEDB_134623,IEDB_136044,IEDB_136100,IEDB_136101,IEDB_137472,IEDB_137485,IEDB_141794,IEDB_144983,IEDB_152206,IEDB_190606,IEDB_433717,IEDB_983930,SB_165,SB_166,SB_187,SB_195,SB_44,SB_67,SB_7,SB_72,SB_88
The structure is contained in the following publication(s):
- Article ID: 824
Ilg T, Craik D, Currie G, Multhaup G, Bacic A "Stage-specific proteophosphoglycan from Leishmania mexicana antastigotes - Structural characterization of novel mono-, di-, and triphosphorylated phosphodiester-linked oligosaccharides" -
Journal of Biological Chemistry 273(22) (1998) 13509-13523
Intracellular amastigotes of the protozoan parasite Leishmania mexicana secrete a macromolecular proteo-phosphoglycan (aPPG) into the phagolysosome of their host cell, the mammalian macrophage. The structures of aPPG glycans were analyzed by a combination of high pH anion exchange high pressure liquid chromatography, gas chromatography-mass spectrometry, enzymatic digestions, electrospray-mass spectrometry as well as 1H and 31P NMR spectroscopy. Some glycans are identical to oligosaccharides known from Leishmania mexicana promastigote lipophosphoglycan and secreted acid phosphatase. However, the majority of the aPPG glycans represent amastigote stage-specific and novel structures. These include neutral glycans ( [Glc(bl-3)(n=1-2)]Gal(bl-4)Man, Gal(bl-3)Gal(bl-4)Man, Gal(bl-3)Glc(bl-3)Gal(bl-4)Man ), several monophosphorylated glycans containing the conserved phosphodisaccharide backbone (R-3-[PO4-6-Gal] (bl-4)Man) but carrying stage-specific modifications ( R = Gal(bl-,[Glc(bl-3)(n=1-2)Glc(bl- ), and monophosphorylated aPPG tri- and tetrasaccharides that are uniquely phosphorylated on the terminal hexose ( PO4-6-Glc(bl-3)Gal(bl-4)Man, PO4-6-Glc(bl-3)Glc(bl-3)Gal(bl-4)Man, PO4-6-Gal(bl-3)Glc(bl-3)Gal(b1-4)Man ). In addition aPPG contains highly unusual di- and triphosphorylated glycans whose major species are PO4-6-Glc(bl-3)Glc(bl-3)[PO4-6-Gal](bl-4)Man, PO4-6-Gal(bl-3)Glc(b1-3)[PO4-6-Gal](bl-4)Man, PO4-6-Gal(bl-3)Glc(bl-3)Glc(bl-3)[PO4-6-Gal](bl-4)Man, PO4-6-Glc(bl-3)[PO4-6-Glc](bl-3)[PO4-6-Gal](b1-4)Man, PO4-6-Gal(bl-3)[PO4-6-Glc](bl-3)Glc(bl-3)[PO4-6-Gal](bl-4)Man, and PO4-6-Glc(bl-3)[PO4-6-Glc](bl-3)Glc(bl-3)[PO4-6-Gal](bl-4)Man. These glycans are linked together by the conserved phosphodiester R-Man-(a1-PO4-6)-Gal-R or the novel phosphodiester R-Man-(a1-PO4-6)-Glc-R and are connected to Ser(P) of the protein backbone most likely via the linkage R-Man-(a1-PO4-Ser). The variety of stage-specific glycan structures in Leishmania mexicana aPPG suggests the presence of developmentally regulated amastigote glycosyl-transferases which may be potential anti-parasite drug targets.
oligosaccharide, structural, characterization, Oligosaccharides, leishmania
NCBI PubMed ID: 9593686Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: thomas.ilg@tuebingen.mpg.de
Institutions: Plant Cell Biology Research Centre, School of Botany, University of Melbourne, Victoria 3052, Australia, Walter and Eliza Hall Institute of Medical Research, P.O. Royal Melbourne Hospital, Victoria 3050, Australia, the Centre for Drug Design and Development, University of Queensland, Brisbane, Queensland 4072, Australia, Centre for Molecular Biology, Heidelberg, Germany
Methods: NMR-2D, GC-MS, ESI-MS, enzymatic digestion, HPAE-HPLC
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2. Compound ID: 4090
b-D-Galp-(1-3)-+
|
b-D-Galp-(1-4)-a-D-Manp-(1--P--6)--b-D-Galp-(1-4)-a-D-Manp-(1--P--6)--b-D-Galp-(1-4)-a-D-Manp-(1--P--1)--Dce-(?--/(CH2)8CH=CH2/
Dce = dec-9-enoic acid |
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Structure type: oligomer
Aglycon: (CH2)8CH=CH2
Compound class: lipophosphoglycan
Contained glycoepitopes: IEDB_130701,IEDB_134623,IEDB_136044,IEDB_136100,IEDB_136101,IEDB_137472,IEDB_141794,IEDB_144983,IEDB_144996,IEDB_152206,IEDB_190606,IEDB_433717,IEDB_983930,SB_165,SB_166,SB_187,SB_195,SB_44,SB_67,SB_7,SB_72,SB_88
The structure is contained in the following publication(s):
- Article ID: 1516
Higson AP, Ross AJ, Tsvetkov YE, Routier FH, Sizova OV, Ferguson MAJ, Nikolaev AV "Synthetic Fragments of Antigenic Lipophosphoglycans from Leishmania major and Leishmania mexicana and Their Use for Characterisation of the Leishmania Elongating a-D-Mannopyranosylphosphate Transferase" -
Chemistry 11(7) (2005) 2019-2030
The phosphorylated branched heptasaccharides 7 and 8, the octasaccharide 9 and the phosphorylated trisaccharides 5 and 6, which are fragments of the phosphoglycan portion of the surface lipophosphoglycans from Leishmania mexicana (5) or L. major (6-9), were synthesised by using the glycosyl hydrogenphosphonate method for the preparation of phosphodiester bridges. The compounds were tested as acceptor substrates/putative inhibitors for the Leishmania elongating α-D-mannosylphosphate transferase.
antigenic, transferase, fragment, Synthetic, characterisation, use, leishmania, P, Leishmania mexicana
NCBI PubMed ID: 15685582Publisher: Vch Verlagsgesellschaft
Correspondence: a.v.nikolaev@dundee.ac.uk
Institutions: Faculty of Life Sciences Division of Biological Chemistry and Molecular Microbiology University of Dundee (Carnelley Building), Dundee DD1 4HN UK, N.D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences, Moscow (Russia), Faculty of Life Sciences Division of Biological Chemistry and Molecular Microbiology University of Dundee (Wellcome Trust Building), Dundee DD1 5EH
Methods: chemical synthesis
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3. Compound ID: 4092
b-D-Galp-(1-3)-+
|
b-D-Galp-(1-3)-b-D-Galp-(1-4)-a-D-Manp-(1--P--6)--b-D-Galp-(1-4)-a-D-Manp-(1--P--6)--b-D-Galp-(1-4)-a-D-Manp-(1--P--1)--Dce-(?--/(CH2)8CH=CH2/
Dce = dec-9-enoic acid |
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Structure type: oligomer
Aglycon: (CH2)8CH=CH2
Compound class: lipophosphoglycan
Contained glycoepitopes: IEDB_130701,IEDB_134623,IEDB_136044,IEDB_136100,IEDB_136101,IEDB_137472,IEDB_141794,IEDB_144983,IEDB_144996,IEDB_152206,IEDB_190606,IEDB_433717,IEDB_983930,SB_165,SB_166,SB_187,SB_195,SB_44,SB_67,SB_7,SB_72,SB_88
The structure is contained in the following publication(s):
- Article ID: 1516
Higson AP, Ross AJ, Tsvetkov YE, Routier FH, Sizova OV, Ferguson MAJ, Nikolaev AV "Synthetic Fragments of Antigenic Lipophosphoglycans from Leishmania major and Leishmania mexicana and Their Use for Characterisation of the Leishmania Elongating a-D-Mannopyranosylphosphate Transferase" -
Chemistry 11(7) (2005) 2019-2030
The phosphorylated branched heptasaccharides 7 and 8, the octasaccharide 9 and the phosphorylated trisaccharides 5 and 6, which are fragments of the phosphoglycan portion of the surface lipophosphoglycans from Leishmania mexicana (5) or L. major (6-9), were synthesised by using the glycosyl hydrogenphosphonate method for the preparation of phosphodiester bridges. The compounds were tested as acceptor substrates/putative inhibitors for the Leishmania elongating α-D-mannosylphosphate transferase.
antigenic, transferase, fragment, Synthetic, characterisation, use, leishmania, P, Leishmania mexicana
NCBI PubMed ID: 15685582Publisher: Vch Verlagsgesellschaft
Correspondence: a.v.nikolaev@dundee.ac.uk
Institutions: Faculty of Life Sciences Division of Biological Chemistry and Molecular Microbiology University of Dundee (Carnelley Building), Dundee DD1 4HN UK, N.D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences, Moscow (Russia), Faculty of Life Sciences Division of Biological Chemistry and Molecular Microbiology University of Dundee (Wellcome Trust Building), Dundee DD1 5EH
Methods: chemical synthesis
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4. Compound ID: 5723
Structure type: oligomer
Compound class: lipophosphoglycan, LPG
Contained glycoepitopes: IEDB_130701,IEDB_134623,IEDB_136044,IEDB_136100,IEDB_136101,IEDB_137472,IEDB_137485,IEDB_141794,IEDB_144983,IEDB_152206,IEDB_190606,IEDB_433717,IEDB_983930,SB_165,SB_166,SB_187,SB_195,SB_44,SB_67,SB_7,SB_72,SB_88
The structure is contained in the following publication(s):
- Article ID: 2500
Ng K, Handman E, Bacic A "Biosynthesis of lipophosphoglycan from Leishmania major: characterization of (β1-3)-galactosyltransferase(s)" -
Glycobiology 4(6) (1994) 845-853
Lipophosphoglycan (LPG) is the major cell surface molecule of promastigotes of all Leishmania species. It is comprised of three domains: a conserved GPI anchor linked to a repeating phosphorylated disaccharide (P2; PO4-6-Gal(β 1-4)Man(α 1-) backbone variously substituted with galactose, glucose and arabinose residues in L.major and capped with a neutral oligosaccharide. Using a microsomal membrane preparation from L.major, we have been able to demonstrate that galactose from UDP-[14C]galactose can be transferred to an endogenous acceptor, characterized as LPG. An in vitro assay was established, based on anion-exchange HPLC, that concurrently identifies and quantitates the products of the galactosyltransferases. We show that the products formed are [14C]galactose-labelled P3 (PO4-6-[Gal(β 1-3)]Gal(β 1-4)Man(α 1-), P4b (PO4-6-[Gal(β 1-3)Gal(β 1-3)]Gal(β 1-4)Man(α 1-) and P5b(PO4-6-[Gal(β 1-3)Gal(β 1-3)Gal(β 1-3)]Gal(β 1- 4)Man(α 1-). These are major galactosylated repeating units of the backbone of L.major LPG. The same products are also formed when LPG from L.donovani, which contains an unbranched backbone of P2 repeats, is used as an exogenous acceptor with L.major microsomal membranes and UDP-[14C]galactose. In addition, no formation of radioactive backbone repeats (P2) was detected in membrane incubations containing UDP-[14C]galactose with or without added unlabelled GDP-mannose, indicating that the addition of the (β 1-3)-linked galactose branches is independent of the synthesis of the repeating disaccharide (P2) backbone. Preliminary kinetic analyses suggest that the addition of multiple (β 1-3)-linked galactose residues may be catalysed by more than one (β 1-3) galactosyltransferase. The (β 1-3)galactosyltransferase(s) activity was not detected in microsomal membrane preparations from promastigotes of L.donovani.
biosynthesis, glycosyltransferases, Galactosyltransferases, leishmania, lipophosphoglycan
NCBI PubMed ID: 7734847Publication DOI: 10.1093/glycob/4.6.845Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Institutions: Walter and Eliza Hall Institute of Medical Research, Royal Melbourne Hospital, Victoria, Australia, Plant Cell Biology Research Centre, School of Botany, University of Melbourne, Victoria, Australia
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5. Compound ID: 5724
Structure type: oligomer
Compound class: lipophosphoglycan, LPG
Contained glycoepitopes: IEDB_130701,IEDB_134623,IEDB_136044,IEDB_136100,IEDB_136101,IEDB_137472,IEDB_137485,IEDB_141794,IEDB_144983,IEDB_152206,IEDB_190606,IEDB_433717,IEDB_581506,IEDB_983930,SB_165,SB_166,SB_187,SB_195,SB_44,SB_67,SB_7,SB_72,SB_88
The structure is contained in the following publication(s):
- Article ID: 2500
Ng K, Handman E, Bacic A "Biosynthesis of lipophosphoglycan from Leishmania major: characterization of (β1-3)-galactosyltransferase(s)" -
Glycobiology 4(6) (1994) 845-853
Lipophosphoglycan (LPG) is the major cell surface molecule of promastigotes of all Leishmania species. It is comprised of three domains: a conserved GPI anchor linked to a repeating phosphorylated disaccharide (P2; PO4-6-Gal(β 1-4)Man(α 1-) backbone variously substituted with galactose, glucose and arabinose residues in L.major and capped with a neutral oligosaccharide. Using a microsomal membrane preparation from L.major, we have been able to demonstrate that galactose from UDP-[14C]galactose can be transferred to an endogenous acceptor, characterized as LPG. An in vitro assay was established, based on anion-exchange HPLC, that concurrently identifies and quantitates the products of the galactosyltransferases. We show that the products formed are [14C]galactose-labelled P3 (PO4-6-[Gal(β 1-3)]Gal(β 1-4)Man(α 1-), P4b (PO4-6-[Gal(β 1-3)Gal(β 1-3)]Gal(β 1-4)Man(α 1-) and P5b(PO4-6-[Gal(β 1-3)Gal(β 1-3)Gal(β 1-3)]Gal(β 1- 4)Man(α 1-). These are major galactosylated repeating units of the backbone of L.major LPG. The same products are also formed when LPG from L.donovani, which contains an unbranched backbone of P2 repeats, is used as an exogenous acceptor with L.major microsomal membranes and UDP-[14C]galactose. In addition, no formation of radioactive backbone repeats (P2) was detected in membrane incubations containing UDP-[14C]galactose with or without added unlabelled GDP-mannose, indicating that the addition of the (β 1-3)-linked galactose branches is independent of the synthesis of the repeating disaccharide (P2) backbone. Preliminary kinetic analyses suggest that the addition of multiple (β 1-3)-linked galactose residues may be catalysed by more than one (β 1-3) galactosyltransferase. The (β 1-3)galactosyltransferase(s) activity was not detected in microsomal membrane preparations from promastigotes of L.donovani.
biosynthesis, glycosyltransferases, Galactosyltransferases, leishmania, lipophosphoglycan
NCBI PubMed ID: 7734847Publication DOI: 10.1093/glycob/4.6.845Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Institutions: Walter and Eliza Hall Institute of Medical Research, Royal Melbourne Hospital, Victoria, Australia, Plant Cell Biology Research Centre, School of Botany, University of Melbourne, Victoria, Australia
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6. Compound ID: 5725
Structure type: oligomer
Compound class: lipophosphoglycan, LPG
Contained glycoepitopes: IEDB_130701,IEDB_134623,IEDB_136044,IEDB_136100,IEDB_136101,IEDB_137472,IEDB_137485,IEDB_141794,IEDB_144983,IEDB_152206,IEDB_156494,IEDB_190606,IEDB_433717,IEDB_983930,SB_165,SB_166,SB_187,SB_195,SB_44,SB_67,SB_7,SB_72,SB_88
The structure is contained in the following publication(s):
- Article ID: 2500
Ng K, Handman E, Bacic A "Biosynthesis of lipophosphoglycan from Leishmania major: characterization of (β1-3)-galactosyltransferase(s)" -
Glycobiology 4(6) (1994) 845-853
Lipophosphoglycan (LPG) is the major cell surface molecule of promastigotes of all Leishmania species. It is comprised of three domains: a conserved GPI anchor linked to a repeating phosphorylated disaccharide (P2; PO4-6-Gal(β 1-4)Man(α 1-) backbone variously substituted with galactose, glucose and arabinose residues in L.major and capped with a neutral oligosaccharide. Using a microsomal membrane preparation from L.major, we have been able to demonstrate that galactose from UDP-[14C]galactose can be transferred to an endogenous acceptor, characterized as LPG. An in vitro assay was established, based on anion-exchange HPLC, that concurrently identifies and quantitates the products of the galactosyltransferases. We show that the products formed are [14C]galactose-labelled P3 (PO4-6-[Gal(β 1-3)]Gal(β 1-4)Man(α 1-), P4b (PO4-6-[Gal(β 1-3)Gal(β 1-3)]Gal(β 1-4)Man(α 1-) and P5b(PO4-6-[Gal(β 1-3)Gal(β 1-3)Gal(β 1-3)]Gal(β 1- 4)Man(α 1-). These are major galactosylated repeating units of the backbone of L.major LPG. The same products are also formed when LPG from L.donovani, which contains an unbranched backbone of P2 repeats, is used as an exogenous acceptor with L.major microsomal membranes and UDP-[14C]galactose. In addition, no formation of radioactive backbone repeats (P2) was detected in membrane incubations containing UDP-[14C]galactose with or without added unlabelled GDP-mannose, indicating that the addition of the (β 1-3)-linked galactose branches is independent of the synthesis of the repeating disaccharide (P2) backbone. Preliminary kinetic analyses suggest that the addition of multiple (β 1-3)-linked galactose residues may be catalysed by more than one (β 1-3) galactosyltransferase. The (β 1-3)galactosyltransferase(s) activity was not detected in microsomal membrane preparations from promastigotes of L.donovani.
biosynthesis, glycosyltransferases, Galactosyltransferases, leishmania, lipophosphoglycan
NCBI PubMed ID: 7734847Publication DOI: 10.1093/glycob/4.6.845Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Institutions: Walter and Eliza Hall Institute of Medical Research, Royal Melbourne Hospital, Victoria, Australia, Plant Cell Biology Research Centre, School of Botany, University of Melbourne, Victoria, Australia
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7. Compound ID: 5726
P-6)-+
|
b-D-Arap-(1-2)-b-D-Galp-(1-3)-b-D-Galp-(1-3)-b-D-Galp-(1-4)-D-Man |
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Structure type: oligomer
Compound class: lipophosphoglycan, LPG
Contained glycoepitopes: IEDB_130701,IEDB_134623,IEDB_136044,IEDB_136100,IEDB_136101,IEDB_137472,IEDB_137485,IEDB_141794,IEDB_144983,IEDB_152206,IEDB_156494,IEDB_190606,IEDB_433717,IEDB_581506,IEDB_983930,SB_165,SB_166,SB_187,SB_195,SB_44,SB_67,SB_7,SB_72,SB_88
The structure is contained in the following publication(s):
- Article ID: 2500
Ng K, Handman E, Bacic A "Biosynthesis of lipophosphoglycan from Leishmania major: characterization of (β1-3)-galactosyltransferase(s)" -
Glycobiology 4(6) (1994) 845-853
Lipophosphoglycan (LPG) is the major cell surface molecule of promastigotes of all Leishmania species. It is comprised of three domains: a conserved GPI anchor linked to a repeating phosphorylated disaccharide (P2; PO4-6-Gal(β 1-4)Man(α 1-) backbone variously substituted with galactose, glucose and arabinose residues in L.major and capped with a neutral oligosaccharide. Using a microsomal membrane preparation from L.major, we have been able to demonstrate that galactose from UDP-[14C]galactose can be transferred to an endogenous acceptor, characterized as LPG. An in vitro assay was established, based on anion-exchange HPLC, that concurrently identifies and quantitates the products of the galactosyltransferases. We show that the products formed are [14C]galactose-labelled P3 (PO4-6-[Gal(β 1-3)]Gal(β 1-4)Man(α 1-), P4b (PO4-6-[Gal(β 1-3)Gal(β 1-3)]Gal(β 1-4)Man(α 1-) and P5b(PO4-6-[Gal(β 1-3)Gal(β 1-3)Gal(β 1-3)]Gal(β 1- 4)Man(α 1-). These are major galactosylated repeating units of the backbone of L.major LPG. The same products are also formed when LPG from L.donovani, which contains an unbranched backbone of P2 repeats, is used as an exogenous acceptor with L.major microsomal membranes and UDP-[14C]galactose. In addition, no formation of radioactive backbone repeats (P2) was detected in membrane incubations containing UDP-[14C]galactose with or without added unlabelled GDP-mannose, indicating that the addition of the (β 1-3)-linked galactose branches is independent of the synthesis of the repeating disaccharide (P2) backbone. Preliminary kinetic analyses suggest that the addition of multiple (β 1-3)-linked galactose residues may be catalysed by more than one (β 1-3) galactosyltransferase. The (β 1-3)galactosyltransferase(s) activity was not detected in microsomal membrane preparations from promastigotes of L.donovani.
biosynthesis, glycosyltransferases, Galactosyltransferases, leishmania, lipophosphoglycan
NCBI PubMed ID: 7734847Publication DOI: 10.1093/glycob/4.6.845Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Institutions: Walter and Eliza Hall Institute of Medical Research, Royal Melbourne Hospital, Victoria, Australia, Plant Cell Biology Research Centre, School of Botany, University of Melbourne, Victoria, Australia
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8. Compound ID: 5727
P-6)-+
|
b-D-Galp-(1-3)-b-D-Galp-(1-3)-b-D-Galp-(1-3)-b-D-Galp-(1-4)-D-Man |
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Structure type: oligomer
Compound class: lipophosphoglycan, LPG
Contained glycoepitopes: IEDB_130701,IEDB_134623,IEDB_136044,IEDB_136100,IEDB_136101,IEDB_136103,IEDB_137472,IEDB_137485,IEDB_141794,IEDB_144983,IEDB_152206,IEDB_156494,IEDB_190606,IEDB_433717,IEDB_983930,SB_165,SB_166,SB_187,SB_195,SB_44,SB_67,SB_7,SB_72,SB_88
The structure is contained in the following publication(s):
- Article ID: 2500
Ng K, Handman E, Bacic A "Biosynthesis of lipophosphoglycan from Leishmania major: characterization of (β1-3)-galactosyltransferase(s)" -
Glycobiology 4(6) (1994) 845-853
Lipophosphoglycan (LPG) is the major cell surface molecule of promastigotes of all Leishmania species. It is comprised of three domains: a conserved GPI anchor linked to a repeating phosphorylated disaccharide (P2; PO4-6-Gal(β 1-4)Man(α 1-) backbone variously substituted with galactose, glucose and arabinose residues in L.major and capped with a neutral oligosaccharide. Using a microsomal membrane preparation from L.major, we have been able to demonstrate that galactose from UDP-[14C]galactose can be transferred to an endogenous acceptor, characterized as LPG. An in vitro assay was established, based on anion-exchange HPLC, that concurrently identifies and quantitates the products of the galactosyltransferases. We show that the products formed are [14C]galactose-labelled P3 (PO4-6-[Gal(β 1-3)]Gal(β 1-4)Man(α 1-), P4b (PO4-6-[Gal(β 1-3)Gal(β 1-3)]Gal(β 1-4)Man(α 1-) and P5b(PO4-6-[Gal(β 1-3)Gal(β 1-3)Gal(β 1-3)]Gal(β 1- 4)Man(α 1-). These are major galactosylated repeating units of the backbone of L.major LPG. The same products are also formed when LPG from L.donovani, which contains an unbranched backbone of P2 repeats, is used as an exogenous acceptor with L.major microsomal membranes and UDP-[14C]galactose. In addition, no formation of radioactive backbone repeats (P2) was detected in membrane incubations containing UDP-[14C]galactose with or without added unlabelled GDP-mannose, indicating that the addition of the (β 1-3)-linked galactose branches is independent of the synthesis of the repeating disaccharide (P2) backbone. Preliminary kinetic analyses suggest that the addition of multiple (β 1-3)-linked galactose residues may be catalysed by more than one (β 1-3) galactosyltransferase. The (β 1-3)galactosyltransferase(s) activity was not detected in microsomal membrane preparations from promastigotes of L.donovani.
biosynthesis, glycosyltransferases, Galactosyltransferases, leishmania, lipophosphoglycan
NCBI PubMed ID: 7734847Publication DOI: 10.1093/glycob/4.6.845Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Institutions: Walter and Eliza Hall Institute of Medical Research, Royal Melbourne Hospital, Victoria, Australia, Plant Cell Biology Research Centre, School of Botany, University of Melbourne, Victoria, Australia
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9. Compound ID: 5952
Structure type: oligomer
Compound class: lipophosphoglycan
Contained glycoepitopes: IEDB_130701,IEDB_134623,IEDB_136044,IEDB_136100,IEDB_136101,IEDB_137472,IEDB_141794,IEDB_144983,IEDB_152206,IEDB_190606,IEDB_433717,IEDB_983930,SB_165,SB_166,SB_187,SB_195,SB_44,SB_67,SB_7,SB_72,SB_88
The structure is contained in the following publication(s):
- Article ID: 2652
McConville MJ, Thomas-Oates JE, Ferguson MAJ, Homans SW "Structure of the lipophosphoglycan from Leishmania major" -
Journal of Biological Chemistry 265 (1990) 19611-19623
The major cell surface glycoconjugate of the parasitic protozoan Leishmania major is a heterogeneous lipophosphoglycan. It has a tripartite structure, consisting of a phosphoglycan (Mr 5,000-40,000), a variably phosphorylated hexasaccharide glycan core, and a lysoalkylphosphatidylinositol (lysoalkyl-PI) lipid anchor. The structures of the phosphoglycan and the hexasaccharide core were determined by monosaccharide analysis, methylation analysis, fast atom bombardment-mass spectrometry, one- and two-dimensional 500-MHz (correlated spectroscopy (COSY), homonuclear Hartmann-Hahn spectroscopy (HOHAHA] 1H NMR spectroscopy, and exoglycosidase digestions. The phosphoglycan consists of eight types of phosphorylated oligosaccharide repeats which have the general structure, [formula: see text] where R = H, Galp(β1-3), Galp(β1-3)Galp(β1-3), Arap(α1-2)Galp(β1-3), Glcp(β1-3)Galp(β1-3), Galp(β1-3)Galp(β1-3)Galp(β1-3), Arap(α1-2)Galp(β1-3)Galp(β1-3), or Arap(α1-2)Galp(β1-3)Galp(β1-3)Galp(β1-3)Galp(β1-3), and where all the monosaccharides, including arabinose, are in the D-configuration. The average number of repeat units/molecule (n) is 27. Data are presented which suggest that the nonreducing terminus of the phosphoglycan is capped exclusively with the neutral disaccharide Manp(α1-2)Manp α1-. The structure of the glycan core was determined to be, [formula: see text] where approximately 60% of the mannose residues distal to the glucosamine are phosphorylated and where the inositol is part of the lysoalkyl-PI lipid moiety containing predominantly 24:0 and 26:0 alkyl chains. The unusual galactofuranose residue is in the β-configuration, correcting a previous report where this residue was identified as α-Galf. Although most of the phosphorylated repeat units are attached to the terminal galactose 6-phosphate of the core to form a linear lipophosphoglycan (LPG) molecule, some of the mannose 6-phosphate residues may also be substituted to form a Y-shaped molecule. The L. major LPG is more complex than the previously characterized LPG from Leishmania donovani, although both LPGs have the same repeating backbone structure and glycolipid anchor. Finally we show that the LPG anchor is structurally related to the major glycolipid species of L. major, indicating that some of these glycolipids may have a function as precursors to LPG.
NCBI PubMed ID: 2246247Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Institutions: Department of Biochemistry, The University, Dundee, United Kingdom
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10. Compound ID: 5953
P-6)-+
|
a-D-Arap-(1-2)-b-D-Galp-(1-3)-b-D-Galp-(1-3)-b-D-Galp-(1-3)-b-D-Galp-(1-4)-a-D-Manp |
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Structure type: oligomer
Compound class: lipophosphoglycan
Contained glycoepitopes: IEDB_130701,IEDB_134623,IEDB_136044,IEDB_136100,IEDB_136101,IEDB_136103,IEDB_137472,IEDB_141794,IEDB_144983,IEDB_152206,IEDB_156494,IEDB_190606,IEDB_433717,IEDB_581506,IEDB_983930,SB_165,SB_166,SB_187,SB_195,SB_44,SB_67,SB_7,SB_72,SB_88
The structure is contained in the following publication(s):
- Article ID: 2652
McConville MJ, Thomas-Oates JE, Ferguson MAJ, Homans SW "Structure of the lipophosphoglycan from Leishmania major" -
Journal of Biological Chemistry 265 (1990) 19611-19623
The major cell surface glycoconjugate of the parasitic protozoan Leishmania major is a heterogeneous lipophosphoglycan. It has a tripartite structure, consisting of a phosphoglycan (Mr 5,000-40,000), a variably phosphorylated hexasaccharide glycan core, and a lysoalkylphosphatidylinositol (lysoalkyl-PI) lipid anchor. The structures of the phosphoglycan and the hexasaccharide core were determined by monosaccharide analysis, methylation analysis, fast atom bombardment-mass spectrometry, one- and two-dimensional 500-MHz (correlated spectroscopy (COSY), homonuclear Hartmann-Hahn spectroscopy (HOHAHA] 1H NMR spectroscopy, and exoglycosidase digestions. The phosphoglycan consists of eight types of phosphorylated oligosaccharide repeats which have the general structure, [formula: see text] where R = H, Galp(β1-3), Galp(β1-3)Galp(β1-3), Arap(α1-2)Galp(β1-3), Glcp(β1-3)Galp(β1-3), Galp(β1-3)Galp(β1-3)Galp(β1-3), Arap(α1-2)Galp(β1-3)Galp(β1-3), or Arap(α1-2)Galp(β1-3)Galp(β1-3)Galp(β1-3)Galp(β1-3), and where all the monosaccharides, including arabinose, are in the D-configuration. The average number of repeat units/molecule (n) is 27. Data are presented which suggest that the nonreducing terminus of the phosphoglycan is capped exclusively with the neutral disaccharide Manp(α1-2)Manp α1-. The structure of the glycan core was determined to be, [formula: see text] where approximately 60% of the mannose residues distal to the glucosamine are phosphorylated and where the inositol is part of the lysoalkyl-PI lipid moiety containing predominantly 24:0 and 26:0 alkyl chains. The unusual galactofuranose residue is in the β-configuration, correcting a previous report where this residue was identified as α-Galf. Although most of the phosphorylated repeat units are attached to the terminal galactose 6-phosphate of the core to form a linear lipophosphoglycan (LPG) molecule, some of the mannose 6-phosphate residues may also be substituted to form a Y-shaped molecule. The L. major LPG is more complex than the previously characterized LPG from Leishmania donovani, although both LPGs have the same repeating backbone structure and glycolipid anchor. Finally we show that the LPG anchor is structurally related to the major glycolipid species of L. major, indicating that some of these glycolipids may have a function as precursors to LPG.
NCBI PubMed ID: 2246247Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Institutions: Department of Biochemistry, The University, Dundee, United Kingdom
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11. Compound ID: 5954
Structure type: oligomer
Compound class: lipophosphoglycan
Contained glycoepitopes: IEDB_130701,IEDB_134623,IEDB_136044,IEDB_136100,IEDB_136101,IEDB_137472,IEDB_141794,IEDB_144983,IEDB_152206,IEDB_190606,IEDB_433717,IEDB_581506,IEDB_983930,SB_165,SB_166,SB_187,SB_195,SB_44,SB_67,SB_7,SB_72,SB_88
The structure is contained in the following publication(s):
- Article ID: 2652
McConville MJ, Thomas-Oates JE, Ferguson MAJ, Homans SW "Structure of the lipophosphoglycan from Leishmania major" -
Journal of Biological Chemistry 265 (1990) 19611-19623
The major cell surface glycoconjugate of the parasitic protozoan Leishmania major is a heterogeneous lipophosphoglycan. It has a tripartite structure, consisting of a phosphoglycan (Mr 5,000-40,000), a variably phosphorylated hexasaccharide glycan core, and a lysoalkylphosphatidylinositol (lysoalkyl-PI) lipid anchor. The structures of the phosphoglycan and the hexasaccharide core were determined by monosaccharide analysis, methylation analysis, fast atom bombardment-mass spectrometry, one- and two-dimensional 500-MHz (correlated spectroscopy (COSY), homonuclear Hartmann-Hahn spectroscopy (HOHAHA] 1H NMR spectroscopy, and exoglycosidase digestions. The phosphoglycan consists of eight types of phosphorylated oligosaccharide repeats which have the general structure, [formula: see text] where R = H, Galp(β1-3), Galp(β1-3)Galp(β1-3), Arap(α1-2)Galp(β1-3), Glcp(β1-3)Galp(β1-3), Galp(β1-3)Galp(β1-3)Galp(β1-3), Arap(α1-2)Galp(β1-3)Galp(β1-3), or Arap(α1-2)Galp(β1-3)Galp(β1-3)Galp(β1-3)Galp(β1-3), and where all the monosaccharides, including arabinose, are in the D-configuration. The average number of repeat units/molecule (n) is 27. Data are presented which suggest that the nonreducing terminus of the phosphoglycan is capped exclusively with the neutral disaccharide Manp(α1-2)Manp α1-. The structure of the glycan core was determined to be, [formula: see text] where approximately 60% of the mannose residues distal to the glucosamine are phosphorylated and where the inositol is part of the lysoalkyl-PI lipid moiety containing predominantly 24:0 and 26:0 alkyl chains. The unusual galactofuranose residue is in the β-configuration, correcting a previous report where this residue was identified as α-Galf. Although most of the phosphorylated repeat units are attached to the terminal galactose 6-phosphate of the core to form a linear lipophosphoglycan (LPG) molecule, some of the mannose 6-phosphate residues may also be substituted to form a Y-shaped molecule. The L. major LPG is more complex than the previously characterized LPG from Leishmania donovani, although both LPGs have the same repeating backbone structure and glycolipid anchor. Finally we show that the LPG anchor is structurally related to the major glycolipid species of L. major, indicating that some of these glycolipids may have a function as precursors to LPG.
NCBI PubMed ID: 2246247Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Institutions: Department of Biochemistry, The University, Dundee, United Kingdom
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12. Compound ID: 5955
Structure type: oligomer
Compound class: lipophosphoglycan
Contained glycoepitopes: IEDB_130701,IEDB_134623,IEDB_136044,IEDB_136100,IEDB_136101,IEDB_137472,IEDB_141794,IEDB_144983,IEDB_152206,IEDB_156494,IEDB_190606,IEDB_433717,IEDB_983930,SB_165,SB_166,SB_187,SB_195,SB_44,SB_67,SB_7,SB_72,SB_88
The structure is contained in the following publication(s):
- Article ID: 2652
McConville MJ, Thomas-Oates JE, Ferguson MAJ, Homans SW "Structure of the lipophosphoglycan from Leishmania major" -
Journal of Biological Chemistry 265 (1990) 19611-19623
The major cell surface glycoconjugate of the parasitic protozoan Leishmania major is a heterogeneous lipophosphoglycan. It has a tripartite structure, consisting of a phosphoglycan (Mr 5,000-40,000), a variably phosphorylated hexasaccharide glycan core, and a lysoalkylphosphatidylinositol (lysoalkyl-PI) lipid anchor. The structures of the phosphoglycan and the hexasaccharide core were determined by monosaccharide analysis, methylation analysis, fast atom bombardment-mass spectrometry, one- and two-dimensional 500-MHz (correlated spectroscopy (COSY), homonuclear Hartmann-Hahn spectroscopy (HOHAHA] 1H NMR spectroscopy, and exoglycosidase digestions. The phosphoglycan consists of eight types of phosphorylated oligosaccharide repeats which have the general structure, [formula: see text] where R = H, Galp(β1-3), Galp(β1-3)Galp(β1-3), Arap(α1-2)Galp(β1-3), Glcp(β1-3)Galp(β1-3), Galp(β1-3)Galp(β1-3)Galp(β1-3), Arap(α1-2)Galp(β1-3)Galp(β1-3), or Arap(α1-2)Galp(β1-3)Galp(β1-3)Galp(β1-3)Galp(β1-3), and where all the monosaccharides, including arabinose, are in the D-configuration. The average number of repeat units/molecule (n) is 27. Data are presented which suggest that the nonreducing terminus of the phosphoglycan is capped exclusively with the neutral disaccharide Manp(α1-2)Manp α1-. The structure of the glycan core was determined to be, [formula: see text] where approximately 60% of the mannose residues distal to the glucosamine are phosphorylated and where the inositol is part of the lysoalkyl-PI lipid moiety containing predominantly 24:0 and 26:0 alkyl chains. The unusual galactofuranose residue is in the β-configuration, correcting a previous report where this residue was identified as α-Galf. Although most of the phosphorylated repeat units are attached to the terminal galactose 6-phosphate of the core to form a linear lipophosphoglycan (LPG) molecule, some of the mannose 6-phosphate residues may also be substituted to form a Y-shaped molecule. The L. major LPG is more complex than the previously characterized LPG from Leishmania donovani, although both LPGs have the same repeating backbone structure and glycolipid anchor. Finally we show that the LPG anchor is structurally related to the major glycolipid species of L. major, indicating that some of these glycolipids may have a function as precursors to LPG.
NCBI PubMed ID: 2246247Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Institutions: Department of Biochemistry, The University, Dundee, United Kingdom
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13. Compound ID: 5956
Structure type: oligomer
Compound class: lipophosphoglycan
Contained glycoepitopes: IEDB_130701,IEDB_134623,IEDB_136044,IEDB_136100,IEDB_136101,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_144983,IEDB_146664,IEDB_152206,IEDB_190606,IEDB_433717,IEDB_983930,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_44,SB_67,SB_7,SB_72,SB_88
The structure is contained in the following publication(s):
- Article ID: 2652
McConville MJ, Thomas-Oates JE, Ferguson MAJ, Homans SW "Structure of the lipophosphoglycan from Leishmania major" -
Journal of Biological Chemistry 265 (1990) 19611-19623
The major cell surface glycoconjugate of the parasitic protozoan Leishmania major is a heterogeneous lipophosphoglycan. It has a tripartite structure, consisting of a phosphoglycan (Mr 5,000-40,000), a variably phosphorylated hexasaccharide glycan core, and a lysoalkylphosphatidylinositol (lysoalkyl-PI) lipid anchor. The structures of the phosphoglycan and the hexasaccharide core were determined by monosaccharide analysis, methylation analysis, fast atom bombardment-mass spectrometry, one- and two-dimensional 500-MHz (correlated spectroscopy (COSY), homonuclear Hartmann-Hahn spectroscopy (HOHAHA] 1H NMR spectroscopy, and exoglycosidase digestions. The phosphoglycan consists of eight types of phosphorylated oligosaccharide repeats which have the general structure, [formula: see text] where R = H, Galp(β1-3), Galp(β1-3)Galp(β1-3), Arap(α1-2)Galp(β1-3), Glcp(β1-3)Galp(β1-3), Galp(β1-3)Galp(β1-3)Galp(β1-3), Arap(α1-2)Galp(β1-3)Galp(β1-3), or Arap(α1-2)Galp(β1-3)Galp(β1-3)Galp(β1-3)Galp(β1-3), and where all the monosaccharides, including arabinose, are in the D-configuration. The average number of repeat units/molecule (n) is 27. Data are presented which suggest that the nonreducing terminus of the phosphoglycan is capped exclusively with the neutral disaccharide Manp(α1-2)Manp α1-. The structure of the glycan core was determined to be, [formula: see text] where approximately 60% of the mannose residues distal to the glucosamine are phosphorylated and where the inositol is part of the lysoalkyl-PI lipid moiety containing predominantly 24:0 and 26:0 alkyl chains. The unusual galactofuranose residue is in the β-configuration, correcting a previous report where this residue was identified as α-Galf. Although most of the phosphorylated repeat units are attached to the terminal galactose 6-phosphate of the core to form a linear lipophosphoglycan (LPG) molecule, some of the mannose 6-phosphate residues may also be substituted to form a Y-shaped molecule. The L. major LPG is more complex than the previously characterized LPG from Leishmania donovani, although both LPGs have the same repeating backbone structure and glycolipid anchor. Finally we show that the LPG anchor is structurally related to the major glycolipid species of L. major, indicating that some of these glycolipids may have a function as precursors to LPG.
NCBI PubMed ID: 2246247Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Institutions: Department of Biochemistry, The University, Dundee, United Kingdom
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14. Compound ID: 5957
P-6)-+
|
a-D-Arap-(1-2)-b-D-Galp-(1-3)-b-D-Galp-(1-3)-b-D-Galp-(1-4)-a-D-Manp |
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Structure type: oligomer
Compound class: lipophosphoglycan
Contained glycoepitopes: IEDB_130701,IEDB_134623,IEDB_136044,IEDB_136100,IEDB_136101,IEDB_137472,IEDB_141794,IEDB_144983,IEDB_152206,IEDB_156494,IEDB_190606,IEDB_433717,IEDB_581506,IEDB_983930,SB_165,SB_166,SB_187,SB_195,SB_44,SB_67,SB_7,SB_72,SB_88
The structure is contained in the following publication(s):
- Article ID: 2652
McConville MJ, Thomas-Oates JE, Ferguson MAJ, Homans SW "Structure of the lipophosphoglycan from Leishmania major" -
Journal of Biological Chemistry 265 (1990) 19611-19623
The major cell surface glycoconjugate of the parasitic protozoan Leishmania major is a heterogeneous lipophosphoglycan. It has a tripartite structure, consisting of a phosphoglycan (Mr 5,000-40,000), a variably phosphorylated hexasaccharide glycan core, and a lysoalkylphosphatidylinositol (lysoalkyl-PI) lipid anchor. The structures of the phosphoglycan and the hexasaccharide core were determined by monosaccharide analysis, methylation analysis, fast atom bombardment-mass spectrometry, one- and two-dimensional 500-MHz (correlated spectroscopy (COSY), homonuclear Hartmann-Hahn spectroscopy (HOHAHA] 1H NMR spectroscopy, and exoglycosidase digestions. The phosphoglycan consists of eight types of phosphorylated oligosaccharide repeats which have the general structure, [formula: see text] where R = H, Galp(β1-3), Galp(β1-3)Galp(β1-3), Arap(α1-2)Galp(β1-3), Glcp(β1-3)Galp(β1-3), Galp(β1-3)Galp(β1-3)Galp(β1-3), Arap(α1-2)Galp(β1-3)Galp(β1-3), or Arap(α1-2)Galp(β1-3)Galp(β1-3)Galp(β1-3)Galp(β1-3), and where all the monosaccharides, including arabinose, are in the D-configuration. The average number of repeat units/molecule (n) is 27. Data are presented which suggest that the nonreducing terminus of the phosphoglycan is capped exclusively with the neutral disaccharide Manp(α1-2)Manp α1-. The structure of the glycan core was determined to be, [formula: see text] where approximately 60% of the mannose residues distal to the glucosamine are phosphorylated and where the inositol is part of the lysoalkyl-PI lipid moiety containing predominantly 24:0 and 26:0 alkyl chains. The unusual galactofuranose residue is in the β-configuration, correcting a previous report where this residue was identified as α-Galf. Although most of the phosphorylated repeat units are attached to the terminal galactose 6-phosphate of the core to form a linear lipophosphoglycan (LPG) molecule, some of the mannose 6-phosphate residues may also be substituted to form a Y-shaped molecule. The L. major LPG is more complex than the previously characterized LPG from Leishmania donovani, although both LPGs have the same repeating backbone structure and glycolipid anchor. Finally we show that the LPG anchor is structurally related to the major glycolipid species of L. major, indicating that some of these glycolipids may have a function as precursors to LPG.
NCBI PubMed ID: 2246247Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Institutions: Department of Biochemistry, The University, Dundee, United Kingdom
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15. Compound ID: 5958
P-6)-+
|
b-D-Galp-(1-3)-b-D-Galp-(1-3)-b-D-Galp-(1-3)-b-D-Galp-(1-4)-a-D-Manp |
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Structure type: oligomer
Compound class: lipophosphoglycan
Contained glycoepitopes: IEDB_130701,IEDB_134623,IEDB_136044,IEDB_136100,IEDB_136101,IEDB_136103,IEDB_137472,IEDB_141794,IEDB_144983,IEDB_152206,IEDB_156494,IEDB_190606,IEDB_433717,IEDB_983930,SB_165,SB_166,SB_187,SB_195,SB_44,SB_67,SB_7,SB_72,SB_88
The structure is contained in the following publication(s):
- Article ID: 2652
McConville MJ, Thomas-Oates JE, Ferguson MAJ, Homans SW "Structure of the lipophosphoglycan from Leishmania major" -
Journal of Biological Chemistry 265 (1990) 19611-19623
The major cell surface glycoconjugate of the parasitic protozoan Leishmania major is a heterogeneous lipophosphoglycan. It has a tripartite structure, consisting of a phosphoglycan (Mr 5,000-40,000), a variably phosphorylated hexasaccharide glycan core, and a lysoalkylphosphatidylinositol (lysoalkyl-PI) lipid anchor. The structures of the phosphoglycan and the hexasaccharide core were determined by monosaccharide analysis, methylation analysis, fast atom bombardment-mass spectrometry, one- and two-dimensional 500-MHz (correlated spectroscopy (COSY), homonuclear Hartmann-Hahn spectroscopy (HOHAHA] 1H NMR spectroscopy, and exoglycosidase digestions. The phosphoglycan consists of eight types of phosphorylated oligosaccharide repeats which have the general structure, [formula: see text] where R = H, Galp(β1-3), Galp(β1-3)Galp(β1-3), Arap(α1-2)Galp(β1-3), Glcp(β1-3)Galp(β1-3), Galp(β1-3)Galp(β1-3)Galp(β1-3), Arap(α1-2)Galp(β1-3)Galp(β1-3), or Arap(α1-2)Galp(β1-3)Galp(β1-3)Galp(β1-3)Galp(β1-3), and where all the monosaccharides, including arabinose, are in the D-configuration. The average number of repeat units/molecule (n) is 27. Data are presented which suggest that the nonreducing terminus of the phosphoglycan is capped exclusively with the neutral disaccharide Manp(α1-2)Manp α1-. The structure of the glycan core was determined to be, [formula: see text] where approximately 60% of the mannose residues distal to the glucosamine are phosphorylated and where the inositol is part of the lysoalkyl-PI lipid moiety containing predominantly 24:0 and 26:0 alkyl chains. The unusual galactofuranose residue is in the β-configuration, correcting a previous report where this residue was identified as α-Galf. Although most of the phosphorylated repeat units are attached to the terminal galactose 6-phosphate of the core to form a linear lipophosphoglycan (LPG) molecule, some of the mannose 6-phosphate residues may also be substituted to form a Y-shaped molecule. The L. major LPG is more complex than the previously characterized LPG from Leishmania donovani, although both LPGs have the same repeating backbone structure and glycolipid anchor. Finally we show that the LPG anchor is structurally related to the major glycolipid species of L. major, indicating that some of these glycolipids may have a function as precursors to LPG.
NCBI PubMed ID: 2246247Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Institutions: Department of Biochemistry, The University, Dundee, United Kingdom
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