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Efficient Sialyltransferase Inhibitors Based on Transition‐State Analogues of the Sialyl Donor
Author(s) -
Müller Bernd,
Schaub Christoph,
Schmidt Richard R.
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(19981102)37:20<2893::aid-anie2893>3.0.co;2-w
Subject(s) - sialyltransferase , chemistry , cytidine , phosphonate , transition state analog , stereochemistry , substrate (aquarium) , carbon atom , transition (genetics) , ring (chemistry) , enzyme , biochemistry , organic chemistry , active site , biology , ecology , gene
A 200‐ to 1000‐fold higher affinity for sialyltransferase is shown by compounds 1 and 2 relative to the natural substrate. These inhibitors, which are derived from the transition state of S N 1‐type sialyltransfer, contain a flat ring that is attached through a carbon atom with a phosphonate and a cytidine monophosphate group.