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A Short Synthetic Route towards a Biologically Active Heparin‐like Pentasaccharide with a Pseudo‐Alternating Sequence
Author(s) -
Lucas Hans,
Basten Jan E. M.,
Konradsson Peter,
van Boeckel Constant A. A.
Publication year - 1993
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.199304341
Subject(s) - disaccharide , epimer , antithrombin , sequence (biology) , chemistry , stereochemistry , biological activity , derivative (finance) , heparin , glycan , biochemistry , glycoprotein , in vitro , economics , financial economics
Simplification of the structure but maintenance of the biological activity —this (successful) strategy was the basis for the synthesis of 1 , the “non‐glycosamino” glycan analogue of the pentasaccharide domain of heparin responsible for binding antithrombin III. The disaccharide corresponding to the EF building block could be prepared from a protected derivative of fragment GH by basecatalyzed epimerization at C5. The number of synthetic steps was thus significantly reduced.