EMAIL THIS PAGE TO A FRIEND

Chemical science

Trimethyl lock: A trigger for molecular release in chemistry, biology, and pharmacology.


PMID 23181187

Abstract

The trimethyl lock is an o-hydroxydihydrocinnamic acid derivative in which unfavorable steric interactions between three pendant methyl groups encourage lactonization to form a hydrocoumarin. This reaction is extremely rapid, even when the electrophile is an amide and the leaving group is an amino group of a small-molecule drug, fluorophore, peptide, or nucleic acid. O-Acylation of the phenolic hydroxyl group prevents reaction, providing a trigger for the reaction. Thus, the release of an amino group from an amide can be coupled to the hydrolysis of a designated ester (or to another chemical reaction that regenerates the hydroxyl group). Trimethyl lock conjugates are easy to synthesize, making the trimethyl lock a highly versatile module for chemical biology and related fields.

Related Materials

Product #

Image

Description

Molecular Formula

Add to Cart

776181
3-(2-Acetoxy-4,6-dimethylphenyl)-3-methylbutyric acid N-succinimidyl ester, 95%
C19H23NO6