Synthesis of monomeric and dimeric repeating units of the zwitterionic type 1 capsular polysaccharide from Streptococcus pneumoniae Journal Article
| Authors: | Wu, X.; Cui, L.; Lipinski, T.; Bundle, D. R. |
| Article Title: | Synthesis of monomeric and dimeric repeating units of the zwitterionic type 1 capsular polysaccharide from Streptococcus pneumoniae |
| Abstract: | Zwitterionic polysaccharides (ZPSs) from Bacteroides fragilis and Streptococcus pneumoniae display unique T-cell activities. The first synthesis of a hexasaccharide representing two repeating units of the zwitterionic capsular polysaccharide from S. pneumoniae type 1 (Sp1) is reported. Key elements of the approach are stereoselective construction of 1,4-as-α-galactose linkages based on a reactive trichloroacetimidate donor that incorporates a 6-O-acetyl group, which may contribute to the high a selectivity in glycosylation, After assembly of the fully protected hexasaccharide from five monosaccharide synthons 2-4, 24 and 25, selective deprotection of the primary hydroxyl groups of the four galactose residues followed by oxidation to the corresponding uronic acids provides hexasaccharide 19. The trisaccharide counterpart 1 was synthesized in similar fashion from three synthons, 2-4. This approach employed both conventional and dehydrative glycosylation methodologies and avoids the use of poorly reactive uronic acid derived glycosyl donors and acceptors. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA. |
| Keywords: | chemistry; glycosylation; glucose; esterification; polysaccharide; polysaccharides; streptococcus pneumoniae; cell activity; oxidation; acids; oxidation reduction reaction; oxidation-reduction; synthesis; hexasaccharides; synthesis (chemical); stereoisomerism; carboxylic acids; t-cell activation; hydroxyl groups; uronic acid; bacteroides fragilis; capsular polysaccharides; fully protected; galactose residues; glycosyl donors; key elements; o-acetyl group; repeating unit; selective deprotection; stereoselective construction; synthons; t cell activation; uronic acids; bacterial polysaccharide; bacterial membrane; bacterial capsules; polysaccharides, bacterial |
| Journal Title: | Chemistry - A European Journal |
| Volume: | 16 |
| Issue: | 11 |
| ISSN: | 0947-6539 |
| Publisher: | Wiley V C H Verlag Gmbh |
| Date Published: | 2010-03-15 |
| Start Page: | 3476 |
| End Page: | 3488 |
| Language: | English |
| DOI: | 10.1002/chem.200902460 |
| PUBMED: | 20146269 |
| PROVIDER: | scopus |
| DOI/URL: | |
| Notes: | --- - "Cited By (since 1996): 2" - "Export Date: 20 April 2011" - "CODEN: CEUJE" - "Source: Scopus" |
