Chemical synthesis of 6(GlcNAc)- and 6(Gal)-O-sulfated SiaLeX tetrasaccharides in spacer-armed form.
Glycobiology, 19 (10), pp. 1078 - 1081, (2009)
1 Laboratory of Carbohydrate Chemistry
2 Department of Instrumental Analytical Methods
3 Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 ul. Miklukho-Maklaya, 117997 Moscow, Russia
Practical synthesis of tetrasaccharide sulfates, 6(GlcNAc)-O-Su-SiaLeX-OCH2CH2CH2NH2 and 6(Gal)-O-Su-SiaLeX-OCH2CH2CH2NH2 (Su=SO3H), selectin ligands, and leukocyte 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≡CH, convenient for "click chemistry" mode conjugation with an azido carrier, particularly, for the synthesis of an immunogen.
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