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

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 bromoacetate ester cross-linking agents.

Results

We found cross-linking between uridine-5'-monophosphorothioate and D-glucosamine using N-hydroxybenzotriazole and N-hydroxysuccinimde bromoacetates to be ineffective. In order to gain insight into these shortfalls, 2-S-(5'-thiophosphoryluridine)acetic acid esters were prepared using p-nitroph

SUBMITTER: Trmcic M 

PROVIDER: S-EPMC2956570 | biostudies-literature | 2010 Aug

REPOSITORIES: biostudies-literature