Journal
CHEMICAL SCIENCE
Volume 3, Issue 8, Pages 2412-2420Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c2sc20536j
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Funding
- Medical Scientist Training Program
- NIH [R01 CA073808, R01 GM044783]
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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.
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