Synthesis of the Trisaccharide Repeating Unit of the O‐Antigen Related to the Enterohemorrhagic Escherichia coli Type O26:H

References

• Levine , M. M. 1987 . Escherichia coli that cause diarrhea: enterotoxigenic, enteropathogenic, enteroinvasive, enterohemorrhagic, and enteroadherent . J. Infect. Dis. , 155 ( 3 ) : 377 – 389 .
   PubMed Web of Science ®Google Scholar
• Manca , M. C. , Weintraub , A. and Widmalm , G. 1996 . Structural studies of the Escherichia coli O26 O‐antigen polysaccharide . Carbohydr. Res. , 281 : 155 – 160 .
   PubMedGoogle Scholar
• Robbins , J. B. , Schneerson , R. , Szu , S. C. and Pozsgay , V. 1999 . Bacterial polysaccharide‐protein conjugate vaccines . Pure Appl. Chem. , 71 ( 9 ) : 745 – 754 .
   Google Scholar
• Pozsgay , V. 1998 . Synthetic Shigella vaccines: a carbohydrate protein conjugate with totally synthetic hexadecasaccharide haptens . Angew. Chem., Int. Ed. Engl. , 37 : 138 – 142 .
   Web of Science ®Google Scholar
• Lemieux , R. U. , Takeda , T. and Chung , B. Y. 1976 . Synthetic methods for carbohydrates . ACS Symp. Ser. , 39 : 90 – 117 .
   Google Scholar
• Kihlberg , J. O. , Leigh , D. A. and Bundle , D. R. 1990 . The in situ activation of thioglycosides with bromine: an improved glycosylation method . J. Org. Chem. , 55 : 2860 – 2863 .
   Web of Science ®Google Scholar
• Jansson , K. , Ahlfors , S. , Frejd , T. , Kihlberg , S. and Magnusson , G. 1988 . 2‐Trimethylsilyl)ethyl glycosides. Synthesis, anomeric deblocking and transformation into 1,2‐trans 1‐O‐acyl sugars . J. Org. Chem. , 53 : 5629 – 5647 .
   Web of Science ®Google Scholar
• Bertolini , M. and Glaudemans , C. P.J. 1970 . The chloroacetyl groups in synthetic carbohydrate chemistry . Carbohydr. Res. , 15 : 263 – 270 .
   Web of Science ®Google Scholar
• Zhang , Z. and Magnusson , G. 1996 . Conversion of p‐methoxyphenyl glycosides into the corresponding glycosyl chlorides and bromides and into thiophenyl glycosides . Carbohydr. Res. , 295 : 41 – 55 .
   PubMed Web of Science ®Google Scholar
• Liptak , A. , Imore , J. and Nanasi , P. 1981 . Preparation of carbohydrate isopropylidene derivatives with 2,2‐dimethoxypropane in the presence of toluene p‐sulfonic acid . Carbohydr. Res. , 92 : 154 – 156 .
   Web of Science ®Google Scholar
• Wessel , H. P. and Bundle , D. R. 1985 . Strategies for the synthesis of branched oligo‐saccharides of the Shigella flexneri 5a, 5b and variant X serogroups employing a multifunctional rhamnose precursor . J. Chem. Soc., Perkin Trans. 1 , : 2251 – 2260 .
   Google Scholar
• Roth , W. and Pigman , W. 1963 . “ d‐Glucal and the glycols ” . In Methods in Carbohydrate Chemistry Edited by: Whistler , R. L. and Wolfrom , M. L. Vol. 2 , 405 – 408 . New York : Academic Press .
   Google Scholar
• Lemieux , R. U. and Ratcliffe , R. M. 1979 . The azidonitration of tri‐O‐acetyl‐d‐galactal . Can. J. Chem. , 57 : 1244 – 1251 .
   Web of Science ®Google Scholar
• Kinzy , W. and Schmidt , R. 1985 . Synthese des trisaccharides aus der “Repeating Unit” des kapselpolysaccharide von Neisseria meningitis des (Sero gruppe l) . Leibigs Ann. Chem. , : 1537 – 1545 .
   Google Scholar
• Wegmann , B. and Schmidt , R. R. 1987 . The application of the trichloroacetinidate method to the synthesis of α‐d gluco and α‐d‐galactopyranosides . J. Carbohydr. Chem. , 6 : 357 – 375 .
   Web of Science ®Google Scholar
• Schmidt , R. R. and Kinzy , W. 1994 . “ Anomeric‐oxygen activation for glycoside synthesis: the trichloroacetimidate method ” . In Advances in Carbohydrate Chemistry Edited by: Whistler , R. L. and BeMiller , J. N. Vol. 50 , 21 – 123 . New York : Academic Press .
   Google Scholar
• Veeneman , G. H. , van Leeuwen , S. H. and van Boom , J. H. 1996 . Iodonium ion promoted reactions at the anomeric center. II. An efficient thioglycoside mediated approach towards the formation of 1,2 trans linked glycosides and glycosidic esters . Tetrahedron Lett. , 31 : 1331 – 1334 .
   Google Scholar
• Zuurmond , H. M. , Veeneman , G. H. , van der Maral , G. A. and van Boom , J. H. 1994 . Iodonium ion assisted synthesis of a haptenic tetrasaccharide fragment corresponding to the inner cell‐wall glycopeptidolipid of Mycobacterium avium serotype 4 . Carbohydr. Res. , 241 : 153 – 164 .
   Google Scholar
• Matsuo , I. , Isomura , M. , Walton , R. and Ajisaka , K. 1996 . A new strategy for the synthesis of the core trisaccharide of asparagine‐linked sugar chains . Tetrahedron Lett. , 37 : 8795 – 8798 .
   Web of Science ®Google Scholar
• van der Ven , J. G.M. , Kerékgyártó , J. , Kamerling , J. P. , Lipták , A. and Vliegenthart , J. F.G. 1994 . Synthesis of a fucosylated and a non‐fucosylated core structure of xylose‐containing carbohydrate chains from N‐glycoproteins . Carbohydr. Res. , 264 : 45 – 62 .
   PubMed Web of Science ®Google Scholar
• Kanie , O. , Crawley , S. C. , Palcic , M. M. and Hindsgaul , O. 1993 . Acceptor‐substrate recognition by N‐acetyl glucosaminyltransferase‐V: critical role of the 4″‐hydroxyl group in β‐d‐GlcpNAc‐(1→2)‐α‐d‐Manp‐(1→6)‐β‐d‐Glcp‐OR . Carbohydr. Res. , 243 : 139 – 164 .
   PubMed Web of Science ®Google Scholar
• Zhang , J. and Kováč , P. 1998 . Synthesis of some analogs of the methyl α‐glycoside of the presumed antigenic determinant of the O‐specific polysaccharide of Vibrio cholerae O:1, Serotype Ogawa . J. Carbohydr. Chem. , 17 ( 3 ) : 341 – 357 .
   Web of Science ®Google Scholar