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Synthesis of Pentasaccharide Fragments Related to the O ‐Specific Polysaccharide of Shigella flexneri Serotype 1a
Author(s) -
Lemanski Gregor,
Ziegler Thomas
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200600078
Subject(s) - chemistry , shigella flexneri , glycosylation , stereochemistry , polysaccharide , glycoside , intramolecular force , derivative (finance) , escherichia coli , organic chemistry , biochemistry , financial economics , economics , gene
The synthesis of the pentasaccharide 5‐aminopentylglycosides α‐ L ‐Rha p ‐(1→3)‐[α‐ D ‐Glc p ‐(1→4)]‐β‐ D ‐Glc p NAc‐(1→2)‐α‐ L ‐Rha p ‐(1→2)‐α‐ L ‐Rha p ‐1‐ O ‐(CH 2 ) 5 NH 2 ( 29 ) andα‐ L ‐Rha p ‐(1→3)‐α‐ L ‐Rha p ‐(1→3)‐[α‐ D ‐Glc p ‐(1→4)]‐β‐ D ‐Glc p NAc‐(1→2)‐α‐ L ‐Rha p ‐1‐ O ‐(CH 2 ) 5 NH 2 ( 28 ), related to the O ‐specific polysaccharide of Shigella flexneri serotype 1a by coupling of the suitably protected trisaccharides α‐ D ‐Glc p ‐(1→4)‐β‐ D ‐Glc p (1→2)‐α‐ L ‐Rha p ‐1‐ O ‐(CH 2 ) 5 NH 2 ( 23 ) and α‐ L ‐Rha p ‐(1→3)‐[α‐ D ‐Glc p ‐(1→4)]‐β‐ D ‐Glc p ‐1‐SPh ( 26 ) with the corresponding rhamnosyl glycosides α‐ L ‐Rha p ‐(1→3)‐α‐ L ‐Rha p ‐1‐SEt ( 17 ) and α‐ L ‐Rha p ‐(1→3)‐α‐ L ‐Rha p ‐1‐ O ‐(CH 2 ) 5 NH 2 ( 13 ), is described. Building blocks 23 and 26 were prepared by intramolecular glycosylation of an unsymmetrically tethered cellobiosamine derivative. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)