Kinetic studies and predictions on the hydrolysis and aminolysis of esters of 2-S-phosphorylacetates

M Trmčić, DRW Hodgson

Index: Trmcic, Milena; Hodgson, David R. W. Beilstein Journal of Organic Chemistry, 2010 , vol. 6, p. 732 - 741

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Citation Number: 4

Abstract

Background: Heterobifunctional cross-linking agents are useful in both protein science and organic synthesis. Aminolysis of reactive esters in aqueous systems is often used in bioconjugation chemistry, but it must compete against hydrolysis processes. Here we study the kinetics of aminolysis and hydrolysis of 2-S-phosphorylacetate ester intermediates that result from displacement of bromide by a thiophosphate nucleophile from commonly used ...