Chemical synthesis of 6(GlcNAc)- and 6(Gal)-O-sulfated SiaLe(X) tetrasaccharides in spacer-armed form

Practical synthesis of tetrasaccharide sulfates, 6((GlcNAc))-O-Su-SiaLe(X)-OCH(2)CH(2)CH(2)NH(2) and 6((Gal))-O-Su-SiaLe(X)-OCH(2)CH(2)CH(2)NH(2) (Su( )SO(3)H), selectin ligands, and leu- kocyte trafficking agents is presented. Both sulfates were synthesized starting from the same precursor, protect...

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Bibliographic Details
Published in:Glycobiology (Oxford) 2009-10, Vol.19 (10), p.1078-1081
Main Authors: Pazynina, Galina, Sablina, Marina, Mayzel, Maxim, Nasonov, Vitaly, Tuzikov, Alexander, Bovin, Nicolai
Format: Article
Language:English
Subjects:
Carbohydrate Sequence
Molecular Sequence Data
Molecular Structure
Oligosaccharides - chemical synthesis
Oligosaccharides - chemistry
Online Access:Get full text
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Summary:Practical synthesis of tetrasaccharide sulfates, 6((GlcNAc))-O-Su-SiaLe(X)-OCH(2)CH(2)CH(2)NH(2) and 6((Gal))-O-Su-SiaLe(X)-OCH(2)CH(2)CH(2)NH(2) (Su( )SO(3)H), selectin ligands, and leu- kocyte trafficking agents is presented. Both sulfates were synthesized starting from the same precursor, protected SiaLe(x), by the conventional procedures of carbohydrate chemistry. The sulfated SiaLe(x) derivative was modified at the spacer group to give 6((Gal))-O-Su-SiaLe(x)- OCH(2)CH(2)CH(2)NH-COCH(2)CH(2)C[triple bond]CH, convenient for "click chemistry" mode conjugation with an azido carrier, particularly, for the synthesis of an immunogen.
ISSN:1460-2423
DOI:10.1093/glycob/cwp093