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Preorganization of the Bioactive Conformation of Sialyl Lewis X Analogues Correlates with Their Affinity to E‐Selectin
Author(s) -
Thoma Gebhard,
Magnani John L.,
Patton John T.,
Ernst Beat,
Jahnke Wolfgang
Publication year - 2001
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 - 10.1002/1521-3773(20010518)40:10<1941::aid-anie1941>3.0.co;2-t
Subject(s) - chemistry , fucose , steric effects , tetrahydropyran , substituent , stereochemistry , tetrasaccharide , galactose , glycan , biochemistry , organic chemistry , ring (chemistry) , polysaccharide , glycoprotein
It pays to be organized : Steric repulsion between fucose and the methyl substituent of the adjacent tetrahydropyran reduces the distance between galactose and fucose in the E‐selectin antagonist 1 compared to the distance in closely related compounds that lack the methyl group. This effect causes a solution conformation of 1 that already resembles its conformation when bound to E‐selectin and, thus, leads to a significantly improved bioactivity.