ISSN:
0947-6539
Keywords:
antithrombotics
;
conformation
;
molecular recognition
;
oligosaccharides
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
An octasulfated pentasaccharide 1 having an L-iduronic acid moiety in a fixed 1C4 conformation was synthesized by the coupling of a triosyl donor 3 with a disaccharide acceptor 4 followed by deprotection and O-sulfation. The acceptor 4 was prepared from the fully acetylated 5-C-allyl-β-D-glucose building block 7 by means of a TMSOTf-promoted glycosylation, intramolecular substitution and ozonolysis of the olefinic bond as the key reactions. Compound 1 showed very low activity in an antithrombin 111-mediated anti-Xa assay; this reflects the importance of the presence of a flexible L-iduronic acid moiety in heparin-like antithrombotics.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/chem.1460020815
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