Found 38 structures.
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1. Compound ID: 4566
|
a-D-Galp-(1-6)-a-D-Galp-(1-3)-b-D-Galf-(1-3)-a-D-Manp-(1-3)-a-D-Manp-(1-4)-a-D-GlcpN-(1-6)-myoIno-(1--P--3)--Gro1ALK2ALK |
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Structure type: oligomer
Trivial name: GPI-anchor
Contained glycoepitopes: IEDB_130701,IEDB_134624,IEDB_136095,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_142349,IEDB_142350,IEDB_144983,IEDB_144993,IEDB_151528,IEDB_151531,IEDB_152206,IEDB_164174,IEDB_190606,IEDB_983930,SB_163,SB_197,SB_44,SB_67,SB_7,SB_72
The structure is contained in the following publication(s):
- Article ID: 1758
Thomas JR, Dwek RA, Rademacher TW "Structure, biosynthesis, and function of glycosylphosphatidylinositols" -
Biochemistry 29 (1990) 5413-5422
The last few years have witnessed an explosion in our knowledge of GPI membrane anchors and related glycolipids and molecules where structure details are available, as illustrated in Figure 2. There is now sufficient information on a handful of these molecules to allow a detailed comparison of their chemical structures. Despite a common structural theme, i.e., the presence of mannoglucosaminyl-PI, a great deal of diversity exists in both the glycan structures and the glycerol-linked aliphatic substituents. The complexities of the structures clearly show that a multitechnique approach is required in the elucidation of their structures. The anticipated publication of more structures from a wider range of organisms may reveal even greater diversity, as well as suggesting possible biosynthetic pathways. The details of a potential biosynthetic pathway in T. brucei are becoming apparent, but confirmation of its importance awaits the isolation and characterization of the enzymes involved. Leishmania, in which LPG, GPIs, GIPLs, and GPI membrane anchors are produced, may also provide an interesting system for biosynthetic studies. The recent description of a GPI biosynthetic system in yeast may provide the crucial breakthroughs necessary in unraveling the enzymes and sugar donors involved in the biosynthetic pathway and possibly the role of the GPI membrane anchor in the function of proteins containing these moieties. Knowledge of the solution structure (conformation), in addition to the complete chemical structure, of the T. brucei VSG anchor has led to speculation that the glycan fulfills a space-filling role in the VSG coat. Many other possible roles of GPI membrane anchors have been suggested, including the shedding and turnover of membrane proteins, signal transduction, and intracellular targeting. Nevertheless, the only function of GPIs that we can so far be certain of is that they anchor proteins or polysaccharide to a membrane. Regardless of the roles GPIs may or may not ultimately be shown to play, the fact that such a widely occurring structure has only recently been characterized serves as a reminder of the incompleteness of our knowledge of biological phenomena and the constant possibility of finding novel molecules in obvious places.
NCBI PubMed ID: 2143679Publication DOI: 10.1021/bi00475a001Journal NLM ID: 0370623Publisher: American Chemical Society
Institutions: Department of Biochemistry, University of Oxford, U.K.
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2. Compound ID: 4929
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a-D-Glcp-(1--P--6)--+
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a-D-Manp-(1--P--6)--a-D-Galp-(1-6)-a-D-Galp-(1-3)-b-D-Galf-(1-3)-a-D-Manp-(1-3)-a-D-Manp-(1-4)-a-D-GlcpN-(1-6)-myoIno |
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Structure type: oligomer
Trivial name: GPL
Compound class: glycolipid
Contained glycoepitopes: IEDB_130701,IEDB_134624,IEDB_136095,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_142349,IEDB_142350,IEDB_142488,IEDB_144983,IEDB_144993,IEDB_144996,IEDB_144998,IEDB_145002,IEDB_146664,IEDB_151528,IEDB_151531,IEDB_152206,IEDB_164174,IEDB_190606,IEDB_474450,IEDB_983930,IEDB_983931,SB_163,SB_192,SB_197,SB_44,SB_67,SB_7,SB_72
The structure is contained in the following publication(s):
- Article ID: 1895
Weller CT, McConville M, Homans SW "Solution structure and dynamics of a glycoinositol phospholipid (GIPL-6) from Leishmania major" -
Biopolymers 34 (1994) 1155-1163
By use of a combination of 1H nuclear Overhauser effect measurements, restrained molecular dynamics simulations, and 13C spin-lattice relaxation time measurements, the solution behavior of the glycan moiety of a complex glycoinositol phospholipid termed GIPL-6, from the protozoan parasite Leishmania major has been determined. The glycan moiety of GIPL-6 has the following structure, which is characterized by the presence of an internal β-galactofuranose residue: [formula: see text] The glycan does not adopt a single conformation in solution, due to significant torsional variations about the two phosphodiester linkages and certain glycosidic linkages in the molecule. The presence of the internal galactofuranose residue results in an average solution conformation of the oligosaccharide, which resembles a "hairpin," with the galactofuranose residue at the apex.
NCBI PubMed ID: 7948729Publication DOI: 10.1002/bip.360340905Journal NLM ID: 0372525Publisher: Wiley Interscience
Institutions: Department of Biochemistry, University of Dundee, United Kingdom
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3. Compound ID: 6381
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b-D-Galp-(1-4)-+ a-D-Glcp-(1--P--6)--+
| |
a-D-Manp-(1-2)-a-D-Manp-(1-2)-a-D-Manp-(1--P--6)--{{{-b-D-Galp-(1-4)-a-D-Manp-(1--P--6)--}}}/n=16/-a-D-Galp-(1-6)-a-D-Galp-(1-3)-b-D-Galf-(1-3)-a-D-Manp-(1-3)-a-D-Manp-(1-4)-a-D-GlcpN-(1-6)-myoIno-(1--P--3)--Gro1ALK |
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Structure type: oligomer
Trivial name: GPI-anchor
Compound class: lipophosphoglycan
Contained glycoepitopes: IEDB_130701,IEDB_134623,IEDB_134624,IEDB_136044,IEDB_136095,IEDB_136100,IEDB_136104,IEDB_136906,IEDB_137472,IEDB_140116,IEDB_141794,IEDB_141807,IEDB_141830,IEDB_142349,IEDB_142350,IEDB_142488,IEDB_143632,IEDB_144983,IEDB_144993,IEDB_144996,IEDB_144998,IEDB_145002,IEDB_146664,IEDB_151528,IEDB_151531,IEDB_152206,IEDB_164174,IEDB_189518,IEDB_190606,IEDB_433717,IEDB_474450,IEDB_983930,IEDB_983931,SB_136,SB_163,SB_165,SB_166,SB_187,SB_192,SB_195,SB_196,SB_197,SB_44,SB_67,SB_7,SB_72,SB_88
The structure is contained in the following publication(s):
- Article ID: 1735
McConville MJ, Ferguson MAJ "The structure, biosynthesis and function of glycosylated phosphatidylinositols in the parasitic protozoa and higher eukaryotes" -
Biochemical Journal 294 (1993) 305-324
No abstract available
NCBI PubMed ID: 8373346Publication DOI: 10.1042/bj2940305Journal NLM ID: 2984726RPublisher: London, UK : Published by Portland Press on behalf of the Biochemical Society
Institutions: Department of Biochemistry, University of Dundee, U.K., Department of Biochemistry, University of Dundee, U.K
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4. Compound ID: 6382
|
b-D-Galp-(1-4)-+ ?%b-D-Glc-(1-3)-+ a-D-Glcp-(1--P--6)--+
| | |
a-D-Manp-(1-2)-a-D-Manp-(1-2)-a-D-Manp-(1--P--6)--{{{-b-D-Galp-(1-4)-a-D-Manp-(1--P--6)--}}}/n=30/-a-D-Galp-(1-6)-a-D-Galp-(1-3)-b-D-Galf-(1-3)-a-D-Manp-(1-3)-a-D-Manp-(1-4)-a-D-GlcpN-(1-6)-myoIno-(1--P--3)--Gro1ALK |
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Structure type: oligomer
Trivial name: GPI-anchor
Compound class: lipophosphoglycan
Contained glycoepitopes: IEDB_130701,IEDB_134623,IEDB_134624,IEDB_136044,IEDB_136095,IEDB_136100,IEDB_136104,IEDB_136906,IEDB_137472,IEDB_140116,IEDB_141794,IEDB_141807,IEDB_141830,IEDB_142349,IEDB_142350,IEDB_142488,IEDB_143632,IEDB_144983,IEDB_144993,IEDB_144996,IEDB_144998,IEDB_145002,IEDB_146664,IEDB_151528,IEDB_151531,IEDB_152206,IEDB_164174,IEDB_189518,IEDB_190606,IEDB_433717,IEDB_474450,IEDB_983930,IEDB_983931,SB_136,SB_163,SB_165,SB_166,SB_187,SB_192,SB_195,SB_196,SB_197,SB_44,SB_67,SB_7,SB_72,SB_88
The structure is contained in the following publication(s):
- Article ID: 1735
McConville MJ, Ferguson MAJ "The structure, biosynthesis and function of glycosylated phosphatidylinositols in the parasitic protozoa and higher eukaryotes" -
Biochemical Journal 294 (1993) 305-324
No abstract available
NCBI PubMed ID: 8373346Publication DOI: 10.1042/bj2940305Journal NLM ID: 2984726RPublisher: London, UK : Published by Portland Press on behalf of the Biochemical Society
Institutions: Department of Biochemistry, University of Dundee, U.K., Department of Biochemistry, University of Dundee, U.K
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5. Compound ID: 6383
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b-D-Galp-(1-4)-+
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a-D-Manp-(1-2)-a-D-Manp-(1-2)-a-D-Manp-(1--P--6)--+ a-D-Glcp-(1--P--6)--+
| |
/Variants 0/-{{{-b-D-Galp-(1-4)-a-D-Manp-(1--P--6)--}}}/n=14-36/-a-D-Galp-(1-6)-a-D-Galp-(1-3)-b-D-Galf-(1-3)-a-D-Manp-(1-3)-a-D-Manp-(1-4)-a-D-GlcpN-(1-6)-myoIno-(1--P--3)--Gro1ALK
/Variants 0/ is:
{{{-b-D-Gal-(1-3)-}}}/n=4-10/-b-D-Gal-(1-3)-
OR (exclusively)
b-Arap-(1-2)-{{{-b-D-Gal-(1-3)-}}}/n=0-2/-b-D-Gal-(1-3)- |
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Structure type: oligomer
Trivial name: GPI-anchor
Compound class: lipophosphoglycan
Contained glycoepitopes: IEDB_130701,IEDB_134623,IEDB_134624,IEDB_136044,IEDB_136095,IEDB_136100,IEDB_136101,IEDB_136103,IEDB_136104,IEDB_136906,IEDB_137472,IEDB_140116,IEDB_141794,IEDB_141807,IEDB_141830,IEDB_142349,IEDB_142350,IEDB_142488,IEDB_143632,IEDB_144983,IEDB_144993,IEDB_144996,IEDB_144998,IEDB_145002,IEDB_146664,IEDB_151528,IEDB_151531,IEDB_152206,IEDB_156494,IEDB_164174,IEDB_189518,IEDB_190606,IEDB_433717,IEDB_474450,IEDB_581506,IEDB_983930,IEDB_983931,SB_136,SB_163,SB_165,SB_166,SB_187,SB_192,SB_195,SB_196,SB_197,SB_44,SB_67,SB_7,SB_72,SB_88
The structure is contained in the following publication(s):
- Article ID: 1735
McConville MJ, Ferguson MAJ "The structure, biosynthesis and function of glycosylated phosphatidylinositols in the parasitic protozoa and higher eukaryotes" -
Biochemical Journal 294 (1993) 305-324
No abstract available
NCBI PubMed ID: 8373346Publication DOI: 10.1042/bj2940305Journal NLM ID: 2984726RPublisher: London, UK : Published by Portland Press on behalf of the Biochemical Society
Institutions: Department of Biochemistry, University of Dundee, U.K., Department of Biochemistry, University of Dundee, U.K
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6. Compound ID: 6387
|
P-6)-+
|
{{{-b-D-Galp-(1-4)-a-D-Manp-(1--P--6)--}}}/n=16/-a-D-Galp-(1-6)-a-D-Galp-(1-3)-b-D-Galf-(1-3)-a-D-Manp-(1-3)-a-D-Manp-(1-4)-a-D-GlcpN-(1-6)-myoIno-(1--P--3)--Gro1ALK2ALK |
Show graphically |
Structure type: oligomer
Trivial name: GPI-anchor
Contained glycoepitopes: IEDB_130701,IEDB_134623,IEDB_134624,IEDB_136044,IEDB_136095,IEDB_136100,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_142349,IEDB_142350,IEDB_144983,IEDB_144993,IEDB_144996,IEDB_151528,IEDB_151531,IEDB_152206,IEDB_164174,IEDB_190606,IEDB_433717,IEDB_474450,IEDB_983930,SB_163,SB_165,SB_166,SB_187,SB_195,SB_197,SB_44,SB_67,SB_7,SB_72,SB_88
The structure is contained in the following publication(s):
- Article ID: 1758
Thomas JR, Dwek RA, Rademacher TW "Structure, biosynthesis, and function of glycosylphosphatidylinositols" -
Biochemistry 29 (1990) 5413-5422
The last few years have witnessed an explosion in our knowledge of GPI membrane anchors and related glycolipids and molecules where structure details are available, as illustrated in Figure 2. There is now sufficient information on a handful of these molecules to allow a detailed comparison of their chemical structures. Despite a common structural theme, i.e., the presence of mannoglucosaminyl-PI, a great deal of diversity exists in both the glycan structures and the glycerol-linked aliphatic substituents. The complexities of the structures clearly show that a multitechnique approach is required in the elucidation of their structures. The anticipated publication of more structures from a wider range of organisms may reveal even greater diversity, as well as suggesting possible biosynthetic pathways. The details of a potential biosynthetic pathway in T. brucei are becoming apparent, but confirmation of its importance awaits the isolation and characterization of the enzymes involved. Leishmania, in which LPG, GPIs, GIPLs, and GPI membrane anchors are produced, may also provide an interesting system for biosynthetic studies. The recent description of a GPI biosynthetic system in yeast may provide the crucial breakthroughs necessary in unraveling the enzymes and sugar donors involved in the biosynthetic pathway and possibly the role of the GPI membrane anchor in the function of proteins containing these moieties. Knowledge of the solution structure (conformation), in addition to the complete chemical structure, of the T. brucei VSG anchor has led to speculation that the glycan fulfills a space-filling role in the VSG coat. Many other possible roles of GPI membrane anchors have been suggested, including the shedding and turnover of membrane proteins, signal transduction, and intracellular targeting. Nevertheless, the only function of GPIs that we can so far be certain of is that they anchor proteins or polysaccharide to a membrane. Regardless of the roles GPIs may or may not ultimately be shown to play, the fact that such a widely occurring structure has only recently been characterized serves as a reminder of the incompleteness of our knowledge of biological phenomena and the constant possibility of finding novel molecules in obvious places.
NCBI PubMed ID: 2143679Publication DOI: 10.1021/bi00475a001Journal NLM ID: 0370623Publisher: American Chemical Society
Institutions: Department of Biochemistry, University of Oxford, U.K.
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7. Compound ID: 6410
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a-D-Glcp-(1--P--6)--+
|
a-D-Manp-(1--P--6)--a-D-Galp-(1-4)-a-D-Manp-(1--P--6)--a-D-Galp-(1-6)-a-D-Galp-(1-3)-b-D-Galf-(1-3)-a-D-Manp-(1-3)-a-D-Manp-(1-4)-a-D-GlcpN-(1-6)-myoIno-(1--P--1)--Gro3ALK |
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Structure type: oligomer
Trivial name: glycolipid
Compound class: lipophosphoglycan
Contained glycoepitopes: IEDB_130701,IEDB_134624,IEDB_136095,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_142349,IEDB_142350,IEDB_142488,IEDB_144983,IEDB_144993,IEDB_144996,IEDB_144998,IEDB_145002,IEDB_146664,IEDB_151528,IEDB_151531,IEDB_152206,IEDB_164174,IEDB_190606,IEDB_474450,IEDB_983930,IEDB_983931,SB_163,SB_192,SB_197,SB_44,SB_67,SB_7,SB_72
The structure is contained in the following publication(s):
- Article ID: 2502
de Lederkremer RM, Colli W "Galactofuranose-containing glycoconjugates in trypanosomatids" -
Glycobiology 5 (1995) 547-552
Galactofuranose has been characterized in glycoinositolphospholipid (GIPL) anchor-like structures having a glycerolipid or a ceramide, as in lipopeptidophosphoglycan (LPPG) of Trypanosoma cruzi, in the oligosaccharide core of lipopeptidophosphoglycan (LPG) of Leishmania species, and also modifying high-mannose chains of trypanosomatid glycoproteins. Galactofuranose is usually present linked β1→3 to Man, either as a terminal non-reducing unit, like in LPPG, or in the middle of the oligosaccharide core, as in LPG. The presence in protozoan parasites of galactose in the furanose configuration is a feature which deserves further attention since the mammalian hosts do not appear to produce glycoconjugates containing this structural unit. For that reason, hosts produce antibodies against galactofuranose, which may turn out to be important in understanding the pathogenesis and in the development of diagnostic methods. The metabolic pathways involved in the attachment to or removal of galactofuranose from glycoconjugates have not yet been elucidated. This is an area of incipient research, but of growing importance, since it will foster the design of inhibitors which may prove to be useful for the treatment of disease.
NCBI PubMed ID: 8563141Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Institutions: Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Argentina
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8. Compound ID: 6420
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a-D-Manp-(1-2)-a-D-Manp-(1--P--6)--+ P-6)-+ /Variants 0/-+
| | |
?%a-D-Arap-(1-2)-{{{-b-D-Galp-(1-3)-}}}/n=0-2/-b-D-Galp-(1-3)-{{{-b-D-Galp-(1-4)-a-D-Manp-(1--P--6)--}}}/n=27/-a-D-Galp-(1-6)-a-D-Galp-(1-3)-b-D-Galf-(1-3)-a-D-Manp-(1-3)-a-D-Manp-(1-4)-a-D-GlcpN-(1-6)-myoIno-(1--P--3)--Gro
/Variants 0/ is:
Lig-(1-1)-
OR (exclusively)
Crt-(1-1)- |
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Structure type: oligomer
Compound class: lipophosphoglycan
Contained glycoepitopes: IEDB_130701,IEDB_134623,IEDB_134624,IEDB_136044,IEDB_136095,IEDB_136100,IEDB_136101,IEDB_136103,IEDB_136104,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_142349,IEDB_142350,IEDB_143632,IEDB_144983,IEDB_144993,IEDB_144996,IEDB_151528,IEDB_151531,IEDB_152206,IEDB_156494,IEDB_164174,IEDB_190606,IEDB_433717,IEDB_474450,IEDB_581506,IEDB_983930,SB_136,SB_163,SB_165,SB_166,SB_187,SB_195,SB_196,SB_197,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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9. Compound ID: 6424
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P-6)-+ 60%a-D-Glcp-(1--P--6)--+
| |
?%a-D-Arap-(1-2)-{{{-b-D-Galp-(1-3)-}}}/n=0-2/-b-D-Galp-(1-3)-{{{-b-D-Galp-(1-4)-a-D-Manp-(1--P--6)--}}}a-D-Galp-(1-6)-a-D-Galp-(1-3)-b-D-Galf-(1-3)-a-D-Manp-(1-3)-a-D-Manp-(1-4)-a-D-GlcpN-(1-6)-myoIno-(1--P--3)--Gro-(1-1)-ALK |
Show graphically |
Structure type: oligomer
Trivial name: GPI-anchor
Contained glycoepitopes: IEDB_130701,IEDB_134623,IEDB_134624,IEDB_136044,IEDB_136095,IEDB_136100,IEDB_136101,IEDB_136103,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_142349,IEDB_142350,IEDB_142488,IEDB_144983,IEDB_144993,IEDB_144996,IEDB_144998,IEDB_145002,IEDB_146664,IEDB_151528,IEDB_151531,IEDB_152206,IEDB_156494,IEDB_164174,IEDB_190606,IEDB_433717,IEDB_474450,IEDB_581506,IEDB_983930,IEDB_983931,SB_163,SB_165,SB_166,SB_187,SB_192,SB_195,SB_197,SB_44,SB_67,SB_7,SB_72,SB_88
The structure is contained in the following publication(s):
- Article ID: 2658
McConville MJ, Homans SW "Identification of the defect in lipophosphoglycan biosynthesis in a non-pathogenic strain of Leishmania major" -
Journal of Biological Chemistry 267 (1992) 5855-5861
The major macromolecule on the surface of the protozoan parasite, Leishmania major, is a complex lipophosphoglycan (LPG), which is anchored to the plasma membrane by an inositol-containing phospholipid. A defect in LPG biosynthesis is thought to be responsible for the avirulence of the L. major strain LRC L119 in mice. In order to identify the nature of this defect we have characterized two truncated forms of LPG, which are accumulated in this strain, by one- and two-dimensional 500-MHz 1H NMR spectroscopy, two-dimensional heteronuclear 1H-31P NMR spectroscopy, methylation analysis, and exoglycosidase digestions. The structures of these glycoinositolphospholipids, termed GIPL-4 and -6, are as follows: [formula: see text] The glycan moieties of GIPL-4 and -6 are identical to the anchor region of LPG, which is also substituted with a Glc-1-PO4 residue in approximately 60% of the structures. However, instead of being capped with chains of phosphorylated oligosaccharide repeat units, both glycan moieties terminate in Man α1-PO4, suggesting that the defect in LPG biosynthesis is in the transfer of galactose to this residue to form the disaccharide backbone of the first repeat unit. These results indicate that the phosphoglycan moiety of LPG is essential for intracellular survival of the parasite and have implications for LPG biosynthesis.
NCBI PubMed ID: 1532574Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Institutions: Department of Biochemistry, University of Dundee, United Kingdom
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10. Compound ID: 6429
|
20%b-D-Glcp-(1-3)-+
|
20%b-D-Galp-(1-4)-+ | a-D-Glcp-(1--P--6)--+
| | |
30%a-D-Manp-(1-2)-a-D-Manp-(1-2)-D-Manp-(1-?)-{{{-b-D-Galp-(1-4)-a-D-Manp-(1--P--6)--}}}/n=20/-a-D-Galp-(1-6)-a-D-Galp-(1-3)-b-D-Galf-(1-3)-a-D-Manp-(1-3)-a-D-Manp-(1-4)-a-D-GlcpN-(1-6)-myoIno-(1--P--3)--Gro-(1-1)-ALK |
Show graphically |
Structure type: oligomer
Trivial name: GPI-anchor
Contained glycoepitopes: IEDB_130701,IEDB_134623,IEDB_134624,IEDB_136044,IEDB_136095,IEDB_136100,IEDB_136104,IEDB_136906,IEDB_137472,IEDB_137485,IEDB_140116,IEDB_141794,IEDB_141807,IEDB_141830,IEDB_142349,IEDB_142350,IEDB_142488,IEDB_143632,IEDB_144983,IEDB_144993,IEDB_144996,IEDB_144998,IEDB_145002,IEDB_146664,IEDB_151528,IEDB_151531,IEDB_152206,IEDB_164174,IEDB_189518,IEDB_190606,IEDB_433717,IEDB_474450,IEDB_983930,IEDB_983931,SB_136,SB_163,SB_165,SB_166,SB_187,SB_192,SB_195,SB_196,SB_197,SB_44,SB_67,SB_7,SB_72,SB_88
The structure is contained in the following publication(s):
- Article ID: 2889
Ilg T, Etges R, Overath P, McConville MJ, Thomas-Oates J, Thomas J, Homans SW, Ferguson MAJ "Structure of Leishmania mexicana lipophosphoglycan" -
Journal of Biological Chemistry 267(10) (1992) 6834-6840
Lipophosphoglycan (LPG) was isolated from the culture supernatant of Leishmania mexicana promastigotes and its structure elucidated by a combination of 1H NMR, fast atom bombardment mass spectrometry, methylation analysis, and chemical and enzymatic modifications. It consists of the repeating phosphorylated oligosaccharides PO4-6Galβ1-4Manα1- and PO4-6[Glcβ1-3]Galβ1-4Manα1-, which are linked together in linear chains by phosphodiester linkages. Each chain of repeat units is linked to a phosphosaccharide core with the structure PO4-6Galα1-6Galα1-3Galfβ1-3[Glcα1-PO4-6]Manα1-3Manα1-4GlcNH2α1-6-myo-inositol, where the myo-inositol residue forms the head group of a lyso-alkylphosphatidylinositol moiety. The nonreducing terminus of the repeat chains appear to be capped with the neutral oligosaccharides Manα1-2Man, Manα1-2Manα1-2Man, or Manα1-2[Galβ1-4]Man. Cellular LPG, isolated from promastigotes, has a very similar structure to the culture supernatant LPG. However, it differs from culture supernatant LPG in the average number of phosphorylated oligosaccharide repeat units (20 versus 28) and in alkyl chain composition. Although culture supernatant LPG contained predominantly C24:0 alkyl chains, cellular LPG contained approximately equal amounts of C24:0 and C26:0 alkyl chains. It is suggested that culture supernatant LPG is passively shed from promastigotes and that it may contribute significantly, but not exclusively, to the "excreted factor" used for serotyping Leishmania spp. Comparison of L. mexicana LPG with the LPGs of Leishmania major and Leishmania donovani indicate that these molecules are highly conserved but that species-specific differences occur in the phosphorylated oligosaccharide repeat branches and in the relative abundance of the neutral cap structures.
NCBI PubMed ID: 1551890Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Institutions: Department of Biochemistry, University of Dundee, Dundee, United Kingdom, Max-Planck-Institut für Biologie, Abteilung Membranbiochemie, Tübingen, Germany
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11. Compound ID: 6431
|
/Variants 0/-+ a-D-Glcp-(1--P--6)--+
| |
b-D-Galp-(1-4)-a-D-Manp-(1--P--6)--{{{-b-D-Galp-(1-4)-a-D-Manp-(1--P--6)--}}}/n=36/-a-D-Galp-(1-6)-a-D-Galp-(1-3)-b-D-Galf-(1-3)-a-D-Manp-(1-3)-a-D-Manp-(1-4)-a-D-GlcpN-(1-6)-myoIno-(1--P--3)--Gro-(1-1)-ALK
/Variants 0/ is:
?%b-D-Glcp-(1-3)-b-D-Glcp-(1-3)-
OR (exclusively)
b-D-Glcp-(1-3)-b-D-Galp-(1-3)-
OR (exclusively)
{{{-b-D-Galp-(1-3)-}}}b-D-Galp-(1-3)- |
Show graphically |
Structure type: oligomer
Trivial name: GPI-anchor
Contained glycoepitopes: IEDB_130701,IEDB_134623,IEDB_134624,IEDB_136044,IEDB_136095,IEDB_136100,IEDB_136101,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_142349,IEDB_142350,IEDB_142488,IEDB_144983,IEDB_144993,IEDB_144996,IEDB_144998,IEDB_145002,IEDB_146664,IEDB_151528,IEDB_151531,IEDB_152206,IEDB_153543,IEDB_156494,IEDB_164174,IEDB_190606,IEDB_433717,IEDB_474450,IEDB_983930,IEDB_983931,SB_163,SB_165,SB_166,SB_187,SB_192,SB_195,SB_197,SB_44,SB_67,SB_7,SB_72,SB_88
The structure is contained in the following publication(s):
- Article ID: 2669
Moody SF, Handman E, McConville MJ, Bacic A "The structure of Leishmania major amastigote lipophosphoglycan" -
Journal of Biological Chemistry 268 (1993) 18457-18466
Intracellular amastigotes of Leishmania major produce 6 x 10(4) copies/cell of a lipophosphoglycan (LPG) that is structurally distinct from the LPG produced by the extracellular promastigote form of L. major, Leishmania donovani, and Leishmania mexicana (reviewed by McConville, M. J. (1991) Cell Biol. Int. Rep. 15, 779-798). L. major amastigote LPG is composed of a lysoalkyl phosphatidylinositol lipid anchor that links via a diphosphorylated hexasaccharide core to a phosphoglycan (6-100 kDa). The structures of the anchor, the core, and the phosphoglycan were determined by monosaccharide and linkage analysis, fast atom bombardment-mass spectrometry, one-dimensional 1H NMR spectroscopy, and exoglycosidase microsequencing. The lipid anchor contains predominantly 1-O-alkylglycerols with 24:0 and 22:0 alkyl chains. The lipids are linked via a glycerol-myo-inositol-PO4 to a core glycan with the structure -PO4-6)Gal(α1-)Gal(α1-)Galf(β1-)[Glc(α1-PO4-)]Man(α1-)Man(α1-)GlcN(α1-). The chromatographic characteristics of the core glycan suggest that the saccharide components are linked similarly in amastigote and promastigote LPG. The phosphoglycan attached to the core consists of -PO4-6)Gal(β1-4)Man(α1- repeats units which are either unsubstituted (70%) or substituted (30%) at the 3-position of the Gal residues with oligosaccharide side chains containing primarily Gal and some Glc. Thirteen different types of side chains were identified with the structures [Gal(β1-3)]x, where x = 1-11, or Glc(1-3)Glc(1-3), or Glc(1-3)Gal(β1-3), where glucose is probably in the β-configuration. All monosaccharides in the phosphoglycan domain are in the pyranose configuration. The average number of repeat units per molecule is 36. The nonreducing terminus of the phosphoglycan chains probably terminates predominantly in the neutral disaccharide Gal(β1-4)Man(α1-. Comparison of the structure of L. major amastigote LPG to L. major promastigote procyclic and metacyclic LPG forms (McConville, M. J., Turco, S. J., Furguson, M. A. J., and Sacks, D. L. (1992) Embo J. 11, 3593-3600) indicates that this molecule is developmentally modified throughout the different stages of the parasites' life cycle.
NCBI PubMed ID: 8360147Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Institutions: Walter and Eliza Hall Institute of Medical Research, Immunoparasitology Unit, Royal Melbourne Hospital, Victoria, Australia, Department of Biochemistry, University of Dundee, Dundee, United Kingdom, Plant Cell Biology Research Center, School of Botany, University of Melbourne, Parkville, Australia
Methods: FAB-MS
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12. Compound ID: 6443
|
b-D-Galp-(1-4)-+ a-D-Glcp-(1--P--6)--+
| |
a-D-Manp-(1-2)-a-D-Manp-(1-2)-a-D-Manp-(1--P--6)--{{{-b-D-Galp-(1-4)-a-D-Manp-(1--P--6)--}}}a-D-Galp-(1-6)-a-D-Galp-(1-3)-b-D-Galf-(1-3)-a-D-Manp-(1-3)-a-D-Manp-(1-4)-a-D-GlcpN-(1-6)-myoIno-(1--P--3)--Gro-(1-1)-ALK |
Show graphically |
Structure type: oligomer
Trivial name: GPI-anchor
Compound class: lipophosphoglycan
Contained glycoepitopes: IEDB_130701,IEDB_134623,IEDB_134624,IEDB_136044,IEDB_136095,IEDB_136100,IEDB_136104,IEDB_136906,IEDB_137472,IEDB_140116,IEDB_141794,IEDB_141807,IEDB_141830,IEDB_142349,IEDB_142350,IEDB_142488,IEDB_143632,IEDB_144983,IEDB_144993,IEDB_144996,IEDB_144998,IEDB_145002,IEDB_146664,IEDB_151528,IEDB_151531,IEDB_152206,IEDB_164174,IEDB_189518,IEDB_190606,IEDB_433717,IEDB_474450,IEDB_983930,IEDB_983931,SB_136,SB_163,SB_165,SB_166,SB_187,SB_192,SB_195,SB_196,SB_197,SB_44,SB_67,SB_7,SB_72,SB_88
The structure is contained in the following publication(s):
- Article ID: 2784
Ferguson MAJ, Brimacombe JS, Cottaz S, Field RA, Guther LS, Homans SW, McConville MJ, Mehlert A, Milne KG, Ralton JE, Roy YA, Schneider P, Zitzmann N "Glycosyl-phosphatidylinositol molecules of the parasite and the host" -
Parasitology 108 (1994) S45-S54
The glycosyl-phosphatidylinositol (GPI) protein-membrane anchors are ubiquitous among the eukaryotes. However, while mammalian cells typically express in the order of 100 thousand copies of GPI-anchor per cell, the parasitic protozoa, particularly the kinetoplastids, express up to 10-20 million copies of GPI-anchor and/or GPI-related glycolipids per cell. Thus GPI-family members dominate the cell surface molecular architecture of these organisms. In several cases, GPI-anchored proteins, such as the variant surface glycoprotein (VSG) of the African trypanosomes, or GPI-related glycolipids, such as the lipophosphoglycan (LPG) of the Leishmania, are known to be essential for parasite survival and infectivity. The highly elevated levels and specialised nature of GPI metabolism in the kinetoplastid parasites suggest that the GPI biosynthetic pathways might be good targets for the development of chemotherapeutic agents. This article introduces the range of GPI structures found in protozoan parasites, and their mammalian hosts, and discusses some aspects of GPI biosynthesis.
NCBI PubMed ID: 8084654Publication DOI: 10.1017/s0031182000075715Journal NLM ID: 0401121Publisher: London, New York, Cambridge University Press
Institutions: Department of Biochemistry, University of Dundee, United Kingdom, Department of Chemistry, University of Dundee, United Kingdom
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13. Compound ID: 6569
|
/Variants 0/-?%b-D-Galp-(1-3)-+ a-D-Glcp-(1--P--6)--+
| |
a-D-Man-(1-2)-a-D-Manp-(1--P--6)--{{{-b-D-Galp-(1-4)-a-D-Manp-(1--P--6)--}}}/n=5-40/-a-D-Galp-(1-6)-a-D-Galp-(1-3)-b-D-Galf-(1-3)-a-D-Manp-(1-3)-a-D-Manp-(1-4)-a-D-GlcpN-(1-6)-myoIno-(1--P--3)--Gro2ALK-(1-1)-ALK
/Variants 0/ is:
?%a-D-Arap-(1-2)-b-D-Galp-(1-3)-
OR (exclusively)
?%b-D-Galp-(1-3)-b-D-Galp-(1-3)-
OR (exclusively)
?%b-D-Glcp-(1-3)-
OR (exclusively)
?%b-D-Galp-(1-3)-
OR (exclusively)
?%a-D-Arap-(1-2)- |
Show graphically |
Structure type: oligomer
Trivial name: GPI-anchor
Compound class: lipophosphoglycan
Contained glycoepitopes: IEDB_130701,IEDB_134623,IEDB_134624,IEDB_136044,IEDB_136095,IEDB_136100,IEDB_136101,IEDB_136104,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_142349,IEDB_142350,IEDB_142488,IEDB_143632,IEDB_144983,IEDB_144993,IEDB_144996,IEDB_144998,IEDB_145002,IEDB_146664,IEDB_151528,IEDB_151531,IEDB_152206,IEDB_156494,IEDB_164174,IEDB_190606,IEDB_433717,IEDB_474450,IEDB_581506,IEDB_983930,IEDB_983931,SB_136,SB_163,SB_165,SB_166,SB_187,SB_192,SB_195,SB_196,SB_197,SB_44,SB_67,SB_7,SB_72,SB_88
The structure is contained in the following publication(s):
- Article ID: 2965
McConville MJ, Turco SJ, Ferguson MAJ, Sacks DL "Developmental modification of lipophosphoglycan during the differentiation of Leishmania major promastigotes to an infectious stage" -
EMBO Journal 11 (1992) 3593-3600
Protozoan parasites of the genus Leishmania produce the novel surface glycoconjugate, lipophosphoglycan (LPG), which is required for parasite infectivity. In this study we show that LPG structure is modified during the differentiation of L. major promastigotes from a less infectious form in logarithmic growth phase to a highly infectious 'metacyclic' form during stationary growth phase. In both stages, the LPGs comprise linear chains of phosphorylated oligosaccharide repeat units which are anchored to the membrane via a glycosyl-phosphatidylinositol glycolipid anchor. During metacyclogenesis there is (i) an approximate doubling in the average number of repeat units per molecule from 14 to 30, (ii) a pronounced decrease in the relative abundance of repeat units with side chains of β Gal or Gal β1-3Gal β1-, and a corresponding increase in repeat units with either no side chains or with side chains of Arap α1-2 Gal β1- and (iii) a decrease in the frequency with which the glycolipid anchor is substituted with a single glucose α1-phosphate residue. While the majority of the LPG phosphoglycan chains are capped with the neutral disaccharide, Man α1-2Man, a significant minority of the chains appeared to terminate in non-phosphorylated repeat units and may represent incompletely capped species. We suggest that the developmental modification of LPG may be important in modulating the binding of promastigotes to receptors in the sandfly midgut and on human macrophages and in increasing the resistance of metacyclic promastigotes to complement-mediated lysis.
differentiation, leishmania, glycosylated phosphatidylinositol, llipophosphoglycan
NCBI PubMed ID: 1396559Journal NLM ID: 8208664Publisher: Eynsham, Oxford: IRL press for the European Molecular Biology Organization
Institutions: Department of Biochemistry, University of Dundee, UK
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14. Compound ID: 15078
|
a-D-Galp-(1--P--6)--+
|
a-D-Galp-(1-6)-a-D-Galp-(1-3)-b-D-Galf-(1-3)-a-D-Manp-(1-3)-a-D-Manp-(1-4)-a-D-GlcpN-(1-6)-myoIno-(1-P |
Show graphically |
Structure type: oligomer
Compound class: GPI-anchor
Contained glycoepitopes: IEDB_130701,IEDB_134624,IEDB_136095,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_142349,IEDB_142350,IEDB_144983,IEDB_144993,IEDB_145001,IEDB_151528,IEDB_151531,IEDB_152206,IEDB_164174,IEDB_190606,IEDB_474450,IEDB_983930,SB_163,SB_197,SB_44,SB_67,SB_7,SB_72
The structure is contained in the following publication(s):
- Article ID: 5886
Al-Maharik N, Tee JA, Nikolaev AV "Glycosylated Compounds of Parasitic Protozoa" -
Book: Microbial Glycobiology: Structures, Relevance and Applications (2010) 477-548
The glycosylphosphatidylinositols (GPIs) are a class of natural glycosylphospholipids that anchor proteins, glycoproteins, and lipophosphoglycans (LPGs) to the membrane of eukaryotic cells. This chapter reviews the progress and recent achievements in the chemical synthesis of the glycoconjugate structures like glycosylphosphatidylinositol anchors and phosphoglycans of the protozoan parasites Trypanosoma brucei, Trypanosoma cruzi, Toxoplasma gondii, Plasmodium falciparum, and Leishmania. Synthetic strategies toward GPI anchors and GPI-related glycoconjugates have matured since the first synthesis published in the early 1990s. Several attractive synthetic routes used for the preparation of the parasitic structures discussed in this chapter. In addition, synthesis of a GPI anchor found in the yeast Saccharomyces cerevisiae and a few structures from the higher eukaryotes have been discussed. A common feature in most of the strategies used (with the exception of CD52 GPIs) is the initial construction of the GPI glycan core having the appropriate orthogonal protecting groups, followed by subsequent introduction of the phosphate moieties. Almost all strategies use benzyl ethers as permanent O-protecting groups.
synthesis, carbohydrates, glycoconjugates, glycolipids, leishmania, Phosphoglycans, Plasmodium, protozoan parasites, Trypanosoma, Toxoplasma
Publication DOI: 10.1016/B978-0-12-374546-0.00026-2Publisher: San Diego USA: Elsevier
Correspondence: a.v.nikolaev@dundee.ac.uk
Editors: Moran AP, Holst O, Brennan P, Von Itzstein M
Institutions: College of Life Sciences, Division of Biological Chemistry and Drug Discovery, University of Dundee, Dundee, DD1 5EH, UK
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15. Compound ID: 15096
|
/Variants 0/-+
|
a-D-Galp-(1-3)-b-D-Galf-(1-3)-a-D-Manp-(1-3)-a-D-Manp-(1-4)-a-D-GlcpN-(1-6)-myoIno-(1--P--3)--Gro1ALK
/Variants 0/ is:
Ste-(1-2)-
OR (exclusively)
Lig-(1-2)-
OR (exclusively)
Crt-(1-2)-
OR (exclusively)
Beh-(1-2)- |
Show graphically |
Structure type: oligomer
Trivial name: type-2 GIPL-2, type-2 GIPL, GIPL-2
Compound class: glycoinositolphospholipid
Contained glycoepitopes: IEDB_130701,IEDB_136095,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_142349,IEDB_144983,IEDB_144993,IEDB_151528,IEDB_151531,IEDB_152206,IEDB_164174,IEDB_190606,IEDB_534865,IEDB_983930,SB_197,SB_44,SB_67,SB_7,SB_72
The structure is contained in the following publication(s):
- Article ID: 5889
Assis RR, Ibraim IC, Noronha FS, Turco SJ, Soares RP "Glycoinositolphospholipids from Leishmania braziliensis and L. infantum: modulation of innate immune system and variations in carbohydrate structure" -
PLoS Neglected Tropical Diseases 6(2) (2012) e1543
The essential role of the lipophosphoglycan (LPG) of Leishmania in innate immune response has been extensively reported. However, information about the role of the LPG-related glycoinositolphospholipids (GIPLs) is limited, especially with respect to the New World species of Leishmania. GIPLs are low molecular weight molecules covering the parasite surface and are similar to LPG in sharing a common lipid backbone and a glycan motif containing up to 7 sugars. Critical aspects of their structure and functions are still obscure in the interaction with the vertebrate host. In this study, we evaluated the role of those molecules in two medically important South American species Leishmania infantum and L. braziliensis, causative agents of visceral (VL) and cutaneous Leishmaniasis (CL), respectively. GIPLs derived from both species did not induce NO or TNF-α production by non-primed murine macrophages. Additionally, primed macrophages from mice (BALB/c, C57BL/6, TLR2-/- and TLR4-/-) exposed to GIPLs from both species, with exception to TNF-α, did not produce any of the cytokines analyzed (IL1-β, IL-2, IL-4, IL-5, IL-10, IL-12p40, IFN-γ) or p38 activation. GIPLs induced the production of TNF-α and NO by C57BL/6 mice, primarily via TLR4. Pre incubation of macrophages with GIPLs reduced significantly the amount of NO and IL-12 in the presence of IFN-γ or lipopolysaccharide (LPS), which was more pronounced with L. braziliensis GIPLs. This inhibition was reversed after PI-specific phospholipase C treatment. A structural analysis of the GIPLs showed that L. infantum has manose rich GIPLs, suggestive of type I and Hybrid GIPLs while L. braziliensis has galactose rich GIPLs, suggestive of Type II GIPLs. In conclusion, there are major differences in the structure and composition of GIPLs from L. braziliensis and L. infantum. Also, GIPLs are important inhibitory molecules during the interaction with macrophages.
carbohydrate, interaction, leishmania, lipophosphoglycan, Leishmania infantum
NCBI PubMed ID: 22389743Publication DOI: 10.1371/journal.pntd.0001543Journal NLM ID: 101291488Publisher: San Francisco, CA: Public Library of Science
Correspondence: rsoares@cpqrr.fiocruz.br
Institutions: Centro de Pesquisas René Rachou, Fundação Oswaldo Cruz - FIOCRUZ, Belo Horizonte, Brazil, Department of Biochemistry, University of Kentucky Medical Center, Lexington, Kentucky, United States of America
Methods: gel filtration, SDS-PAGE, TLC, ELISA, acid hydrolysis, deamination, FACE, HPLC, immunoblotting, statistical analysis, flow cytometry analysis, cytokine production
- Article ID: 5890
Assis RR, Ibraim IC, Nogueira PM, Soares RP, Turco SJ "Glycoconjugates in New World species of Leishmania: Polymorphisms in lipophosphoglycan and glycoinositolphospholipids and interaction with hosts" -
Biochimica et Biophysica Acta: General Subjects 1820(9) (2012) 1354-1365
Background: Protozoan parasites of the genus Leishmania cause a number of important diseases in humans and undergo a complex life cycle, alternating between a sand fly vector and vertebrate hosts. The parasites have a remarkable capacity to avoid destruction in which surface molecules are determinant for survival. Amongst the many surface molecules of Leishmania, the glycoconjugates are known to play a central role in host-parasite interactions and are the focus of this review. Scope of the review: The most abundant and best studied glycoconjugates are the Lipophosphoglycans (LPGs) and glycoinositolphospholipids (GIPLs). This review summarizes the main studies on structure and biological functions of these molecules in New World Leishmania species. Major conclusions: LPG and GIPLs are complex molecules that display inter- and intraspecies polymorphisms. They are key elements for survival inside the vector and to modulate the vertebrate immune response during infection. General significance: Most of the studies on glycoconjugates focused on Old World Leishmania species. Here, it is reported some of the studies involving New World species and their biological significance on host-parasite interaction. This article is part of a Special Issue entitled Glycoproteomics.
leishmania, lipophosphoglycan, glycoinositolphospholipids, Host–parasite interaction, New World
NCBI PubMed ID: 22093608Publication DOI: 10.1016/j.bbagen.2011.11.001Journal NLM ID: 0217513Publisher: Elsevier
Correspondence: S.J. Turco
Institutions: Centro de Pesquisas René Rachou, Fundação Oswaldo Cruz, FIOCRUZ, Av. Augusto de Lima, 1715, Belo Horizonte, MG 30190-002, Brazil, Department of Biochemistry, University of Kentucky Medical Center, 741 South Limestone, Lexington, KY 40536, USA
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Next 15 structure(s)
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