Thiol Catalysis of Selenosulfide Bond Cleavage by a Triarylphosphine

ABSTRACT: The arylthiol 4-mercaptophenylacetic acid (MPAA) is a powerful catalyst of selenosulfide bond reduction by the trisodium salt (TPPTS). Both reagents are water-soluble at neutral pH and are particularly adapted for working with unprotected peptidic substrates. Contrary to trialkylphosphines such as tris(2carboxyethyl)phosphine hydrochloride (TCEP), TPPTS has the advantage of not inducing deselenization reactions. We believe that the work reported here will be of value for those manipulating selenosulfide bonds in peptidic or protein molecules.

Automated summary

The arylthiol 4-mercaptophenylacetic acid is a powerful catalyst for the reduction of selenosulfide bonds by the water-soluble trisodium salt. It is particularly suitable for working with unprotected peptidic substrates and does not induce deselenization reactions.