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Synthesis of Fucopeptides as Sialyl Lewis x Mimetics
Author(s) -
Wu ShihHsiung,
Shimazaki Makoto,
Lin ChunCheng,
Qiao Lei,
Moree Wilna J.,
WeitzSchmidt Gabriele,
Wong ChiHuey
Publication year - 1996
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199600881
Subject(s) - chemistry , fucose , threonine , biochemistry , butyric acid , stereochemistry , glycoprotein , enzyme , serine
The same biological activity as the antigen determinant sialyl Lewis x was shown by the fucopeptide 1 in a binding assay with E‐selectin. In the design of this mimetic the type and spatial arrangement of the functional groups essential for the interaction between sialyl Lewis x and E‐selectin were considered. Fucopeptide 1 , which may have potential as an antiinflammatory agent, was synthesized from L‐fucose. L‐threonine, (2 S ,3 R )‐2‐amino‐3,4‐dihydroxy‐butyric acid, and glutarate.