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Glycobiology Advance Access originally published online on July 7, 2009
Glycobiology 2009 19(10):1078-1081; doi:10.1093/glycob/cwp093
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© The Author 2009. Published by Oxford University Press. All rights reserved. For permissions, please e-mail: journals.permissions@oxfordjournals.org

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

Galina Pazynina2, Marina Sablina2, Maxim Mayzel3, Vitaly Nasonov2, Alexander Tuzikov2 and Nicolai Bovin1,2

2 Laboratory of Carbohydrate Chemistry
3 Department of Instrumental Analytical Methods, Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 ul. Miklukho-Maklaya, 117997 Moscow, Russia

1 To whom correspondence should be addressed: Tel: +7(495)-330-71-38; Fax: +7(495)-330-55-92; e-mail: bovin{at}carb.ibch.ru

Received on April 15, 2009; revised on June 17, 2009; accepted on June 21, 2009

Practical synthesis of tetrasaccharide sulfates, 6(GlcNAc)-O-Su-SiaLeX-OCH2CH2CH2NH2 and 6(Gal)-O-Su-SiaLeX-OCH2CH2CH2NH2 (SuFormula SO3H), selectin ligands, and leu- kocyte trafficking agents is presented. Both sulfates were synthesized starting from the same precursor, protected SiaLex, by the conventional procedures of carbohydrate chemistry. The sulfated SiaLex derivative was modified at the spacer group to give 6(Gal)-O-Su-SiaLex- OCH2CH2CH2NH-COCH2CH2C{equiv}CH, convenient for "click chemistry" mode conjugation with an azido carrier, particularly, for the synthesis of an immunogen.

Key words: leukocyte trafficking agents / selectin ligands / sulfates of sialyl LewisX


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