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Synthesis and Biological Evaluation of S ‐Neofucopeptides as E‐ and P‐Selectin Inhibitors
Author(s) -
MorenoVargas Antonio J.,
Molina Lidia,
Carmona Ana T.,
Ferrali Alessandro,
Lambelet Martine,
Spertini Olivier,
Robina Inmaculada
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200800199
Subject(s) - chemistry , stereochemistry , combinatorial chemistry , computational biology , biology
The synthesis of α/β‐ L ‐fucosylated cysteamine, 3‐thiopropionic acid, and 3‐thioacetic acid derivatives as building blocks for the preparation of S ‐neofucopeptides is shown. These compounds were used in the synthesis of new thiofucosides derivatives ( 8 α, 9 α, 9 β, 10 α, 22 α, 22 β, 24 α, 26 α) that show affinity towards E‐ and P‐selectins. They constitute a new series of hydrolytically stable and low‐molecular‐weight mimetics of the natural SLe x tetrasaccharide. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)