Thiol-Ene Reaction of Heparin Allyl Ester, Heparin 4-Vinylbenzyl Ester and Enoxaparin

Abstract

Heparin allyl ester and heparin 4-vinylbenzyl ester were prepared and examined for their potential for thiol-ene reaction using both free radical initiators and photochemistry. While both undergo reaction with mercaptoacetic acid, the allyl ester adduct proved to be somewhat more labile. Several more examples of adducts from heparin 4-vinylbenzyl ester are reported. Similar reactions on enoxaparin, where the reaction site is solely at the non-reducing end of the molecule, are also reported. These reactions may show promise as a strategy in the development of drug conjugates.