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Displayed structure 1
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1. Compound ID: 5962
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b-D-GalpNAc-(1-3)-b-D-GalpNAc-(1-3)-a-D-Galp-(1-4)-b-D-Galp-(1-4)-b-D-Glcp-(1-?)-CER-(?--/Ceramide/ |
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Structure type: oligomer
Aglycon: Ceramide
Trivial name: IV3GalNAcb-Gb4-Cer, para-Forssman glycolipid
Compound class: glycosphingolipid
Contained glycoepitopes: IEDB_130648,IEDB_130651,IEDB_136044,IEDB_136906,IEDB_137339,IEDB_137472,IEDB_137473,IEDB_1391964,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_144987,IEDB_146664,IEDB_151528,IEDB_152217,IEDB_190606,IEDB_423106,IEDB_742247,IEDB_983931,SB_165,SB_166,SB_167,SB_178,SB_18,SB_187,SB_19,SB_192,SB_195,SB_21,SB_27,SB_3,SB_31,SB_5,SB_6,SB_62,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 2655
McConville MJ, Blackwell JM "Developmental changes in the glycosylated phosphatidylinositols of Leishmania donovani. Characterization of the promastigote and amastigote glycolipids" -
Journal of Biological Chemistry 266 (1991) 15170-15179
In addition to utilizing glycosylated phosphatidylinositols (GPIs) as anchors for surface proteins, protozoan parasites of the genus Leishmania synthesize two novel classes of GPI: the polydisperse lipophosphoglycans (LPGs) and a family of low molecular weight glycoinositol phospholipids (GIPLs). We now show that LPG is expressed in high copy number (6 x 10(6) molecules/cell) in the promastigote (insect) stage of L. donovani but not in the amastigote stage, which infects mammalian macrophages. Detection of these molecules was by gas chromatography-mass spectrometric analyses and by a sensitive radiolabeling procedure. In contrast, a novel family of GIPLs was present in high copy number (approximately 10(7) molecules/cell) in both promastigote and amastigote stages of L. donovani. These glycolipids were purified and analyzed by gas chromatography-mass spectrometry, methylation analysis, and by chemical and enzymatic sequencing after deamination and NaB3H4 reduction. Promastigotes contained three major GIPLs species with the following generalized structure [formula: see text] where R = H for isoM2, Man α1- for isoM3 or Man α1-2Man α1- for isoM4. Amastigotes contained two major GIPL species that lacked the α1-3-linked mannose branch and had the linear structures Man α1-6Man α1-4GlcN (M2) and Man α1-2Man α1-6Man α1-4GlcN (M3) linked to alkylacyl-PI. The 1-O-alkyl-2-acyl-PI moieties of all these species contained predominantly C18:0 alkyl chains and C16:0 or C18:0 fatty acids. Amastigotes contained, in addition, a GalNAc β1-3 terminating glycosphingolipid with homology to the mammalian para Forssman glycolipid. This glycolipid appeared to be a constituent of the parasite membrane but was not metabolically labeled with [3H]glucose, suggesting that it was acquired from host cells. These results suggest that LPG may not be required for amastigote survival in the mammalian host and that the GIPLs are likely to be major components on the surface membrane in both stages.
NCBI PubMed ID: 1831200Journal 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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