Taxonomic group: bacteria / Spirochaetes
(Phylum: Spirochaetes)
Associated disease: Lyme disease [ICD11:
1C1G 
, ICD11:
XN13C ]
The structure was elucidated in this paperNCBI PubMed ID: 12799465Publication DOI: 10.1073/pnas.1232451100Journal NLM ID: 7505876Publisher: National Academy of Sciences
Correspondence: Ben-Menachem G <gilben
nih.gov>
Institutions: Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, Wroclaw, Poland, Laboratory of Developmental and Molecular Immunity, National Institute of Child Health and Human Development, National Institutes of Health, Bethesda, USA, Laboratory of Cellular and Molecular Biophysics, National Institute of Child Health and Human Development, National Institutes of Health, Bethesda, USA
Two major glycolipids, which comprise ≈36% of the total lipid mass from Borrelia burgdorferi, the etiological agent of Lyme disease, were investigated. We determined the fatty acid type, sugar identity, anomeric configuration, and substituent type and position. The structures were identified as cholesteryl 6-O-acyl-β-d-galactopyranoside (B. burgdorferi glycolipid 1, BbGL-I), and 1,2-di-O-acyl-3-O-α-d-galactopyranosyl-sn-glycerol (BbGL-II). The major fatty acids were palmitate and oleate. The structures were corroborated by gas-liquid chromatography MS, matrix-assisted laser desorption/ionization time-of-flight spectroscopy, fast atom bombardment MS, detailed NMR spectrometry, and metabolic labeling. This is a previously undescribed demonstration of a cholesteryl galactoside in bacteria. Lipopolysaccharide was not detected in B. burgdorferi. The two glycolipids have several properties suggesting they may function as lipopolysaccharide: both are main components of the bacterial membrane, surface exposed, and have a three-domain structure. BbGL-I elicited specific antibodies in mice and rabbits, and BbGL-II elicited antibodies that reacted with both glycolipids.
glycolipid, Borrelia burgdorferi, Lyme disease, galactoside
Structure type: monomer ; 809.87-835.87 [M+Na]+
Location inside paper: Fig.5, BbGL-I, Table 2, BbGL-I
Compound class: glycolipid, glycoside
Contained glycoepitopes: IEDB_136906,IEDB_137472,IEDB_141181,IEDB_141794,IEDB_151528,IEDB_187036,IEDB_190606,SB_7
Methods: 13C NMR, 1H NMR, methylation, GLC-MS, deacetylation, NMR-2D, FAB-MS, TLC, MALDI-TOF MS, biological assays, radiolabeling, enzymatic digestion, extraction, affinity chromatography, acetylation, methylation analysis, reduction, hydrolysis, CC, cell growth, derivatization, evaporation, centrifugation
Biological activity: BbGL-I elicited antibodies in mice and rabbits, mostly of the IgM isotype.
Related record ID(s): 45776, 45777, 45778
NCBI Taxonomy refs (TaxIDs): 224326,
139,
521007
Show glycosyltransferases
NMR conditions: in CDCl3 at 300(H) K
[as TSV]
13C NMR data:
missing...
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3 aDGalp 4.327 3.617 3.617 3.877 3.666 4.300-4.346
Subst
3,6 lXOle
3,6 lXPam
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3 | aDGalp | 4.327 | 3.617 | 3.617 | 3.877 | 3.666 | 4.300
4.346 |
| | Subst | |
| 3,6 | lXOle | |
| 3,6 | lXPam | |
|
There is only one chemically distinct structure:
Found 
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(later renamed to: Borreliella burgdorferi B31 ATCC 35210)