Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 9, Issue 22, Pages 7659-7662Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c1ob06276j
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Funding
- National Institutes of Health (NIAID) [P01 AI053725]
- NATIONAL INSTITUTE OF ALLERGY AND INFECTIOUS DISEASES [P01AI053725] Funding Source: NIH RePORTER
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Natural killer T (NKT) cells recognize glycolipids produced by Sphingomonas bacteria, and these glycolipids contain C6-oxidized sugars, either glucuronic acid or galacturonic acid, linked to ceramides. Glycolipids with gluco stereochemistry are the most prevalent. Multiple studies have demonstrated that galactosylceramides are more potent stimulators of NKT cells than their glucose isomers. To determine if this stereoselectivity is retained in the context of the C6-oxidized sugars found in bacterial glycolipids, we prepared two sets of gluco and galacto-glycolipids oxidized at their C6 positions and compared their NKT stimulatory properties. In the context of carboxylic acid groups at C6, gluco stereochemistry gave the more potent responses. We also prepared bacterial glycolipids containing more complex ceramide groups to determine if these chains impact NKT cell responses.
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