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Parallel Synthesis of Sialyl Lewis X Mimetics on a Solid Phase: Access to a Library of Fucopeptides
Author(s) -
Lampe Thomas F. J.,
WeitzSchmidt Gabriele,
Wong ChiHuey
Publication year - 1998
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(19980703)37:12<1707::aid-anie1707>3.0.co;2-v
Subject(s) - combinatorial chemistry , ethylene glycol , chemistry , acetal , surface modification , copolymer , lewis acids and bases , peg ratio , solid phase synthesis , phase (matter) , polymer chemistry , stereochemistry , organic chemistry , catalysis , biochemistry , peptide , finance , economics , polymer
A novel anchoring group p ‐(acyloxymethyl)benzylidene acetal ( p ‐AMBA) enables the bidirectional functionalization of glycosylated amino acid derivatives and thus the rapid parallel synthesis of fucopeptides as sialyl Lewis X mimetics on a solid phase [Eq. (a), PEG‐PS=poly(ethylene glycol) graft copolymer]. This led to the discovery of new mimetics against P‐selectin with IC 50 values in the low μ M range.