Document Detail


The galactosamine residue in mycobacterial arabinogalactan is alpha-linked.
MedLine Citation:
PMID:  23043372     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
Previous studies have demonstrated that cell wall arabinogalactan from mycobacteria possesses a single galactosamine (GalN) residue. This moiety, which is one the rare natural occurrences of galactosamine lacking an acetyl group on the nitrogen, has been identified as a pendant substituent attached to a highly branched arabinofuranose residue in the arabinan core. However, the stereochemistry by which the GalN residue is linked to the polysaccharide remains unknown. We report here the synthesis of two tetrasaccharides, 1 and 2, consisting of GalN attached through either an alpha or beta-linkage to a trisaccharide fragment of mycobacterial arabinan. These molecules represent the first synthetic GalN-containing oligosaccharides and their preparation of both targets was achieved from a single donor species by modulation of the reaction solvent. Comparison of the NMR spectra of 1 and 2 with those obtained from a sample derived from the natural glycan revealed that the GalN residue in the polysaccharide is attached via an alpha-linkage.
Authors:
Wenjie Peng; Lu Zou; Suresh Bhamidi; Michale R McNeil; Todd L Lowary
Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2012-10-8
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  -     ISSN:  1520-6904     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2012 Oct 
Date Detail:
Created Date:  2012-10-9     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
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