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

Practical synthesis of tetrasaccharide sulfates, 6[sup](GlcNAc)-O-Su-SiaLe[sup]X-OCH[sub]2CH[sub]2CH[sub]2NH[sub]2 and 6[sup](Gal)-O-Su-SiaLe[sup]X-OCH[sub]2CH[sub]2CH[sub]2NH[sub]2 (SuSO[sub]3H), selectin ligands, and leu- kocyte trafficking agents is presented. Both sulfates were synthesized start...

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Bibliographic Details
Published in:Glycobiology (Oxford) 2009-10, Vol.19 (10), p.1078
Main Authors: Pazynina, Galina, Sablina, Marina, Mayzel, Maxim, Nasonov, Vitaly, Tuzikov, Alexander, Bovin, Nicolai
Format: Article
Language:English
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Summary:Practical synthesis of tetrasaccharide sulfates, 6[sup](GlcNAc)-O-Su-SiaLe[sup]X-OCH[sub]2CH[sub]2CH[sub]2NH[sub]2 and 6[sup](Gal)-O-Su-SiaLe[sup]X-OCH[sub]2CH[sub]2CH[sub]2NH[sub]2 (SuSO[sub]3H), selectin ligands, and leu- kocyte trafficking agents is presented. Both sulfates were synthesized starting from the same precursor, protected SiaLe[sup]x, by the conventional procedures of carbohydrate chemistry. The sulfated SiaLe[sup]x derivative was modified at the spacer group to give 6[sup](Gal)-O-Su-SiaLe[sup]x- OCH[sub]2CH[sub]2CH[sub]2NH-COCH[sub]2CH[sub]2C≡CH, convenient for "click chemistry" mode conjugation with an azido carrier, particularly, for the synthesis of an immunogen.
ISSN:0959-6658
1460-2423
DOI:10.1093/glycob/cwp093