Toward synthesis of the isosteric sulfonate analogues of the AT-III binding domain of heparin

Mihály Herczeg; László Lázár; Anikó Borbás; András Lipták; Sándor Antus

doi:10.1021/ol900952d

Toward synthesis of the isosteric sulfonate analogues of the AT-III binding domain of heparin

Org Lett. 2009 Jun 18;11(12):2619-22. doi: 10.1021/ol900952d.

Authors

Mihály Herczeg¹, László Lázár, Anikó Borbás, András Lipták, Sándor Antus

Affiliation

¹ Research Group for Carbohydrates of the Hungarian Academy of Sciences, P.O. Box 94, H-4010 Debrecen, Hungary.

PMID: 19473011
DOI: 10.1021/ol900952d

Abstract

D-glucuronate and l-iduronate containing disaccharides related to the antithrombin-binding pentasaccharide of heparin, in which one of the sulfate esters is systematically replaced by a sodium sulfonatomethyl moiety, were synthesized. The sulfonic acid group was introduced by stereoselective radical addition onto the exomethylene moiety of the appropriate glycoside derivatives, and the resulting sulfonatomethyl glucosides were used as acceptors.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Aminoimidazole Carboxamide / chemical synthesis*
Antithrombin III / chemistry*
Binding Sites
Glucuronates / chemical synthesis
Glucuronates / chemistry
Heparin / chemical synthesis*
Heparin / chemistry
Iduronic Acid / chemical synthesis*
Iduronic Acid / chemistry
Molecular Structure
Oligosaccharides / chemistry*
Pyrazines / chemical synthesis*
Pyrazines / chemistry
Stearic Acids / chemical synthesis
Stearic Acids / chemistry
Structure-Activity Relationship
Sulfonic Acids / chemical synthesis*
Sulfonic Acids / chemistry

Substances

Glucuronates
Oligosaccharides
Pyrazines
Stearic Acids
Sulfonic Acids
Iduronic Acid
Aminoimidazole Carboxamide
Antithrombin III
Heparin
isostearic acid