Synthesis of novel peptide linkers: simultaneous cyclization and labeling

Gajanan K Dewkar; Pedro B Carneiro; Matthew C T Hartman

doi:10.1021/ol901662c

Synthesis of novel peptide linkers: simultaneous cyclization and labeling

Org Lett. 2009 Oct 15;11(20):4708-11. doi: 10.1021/ol901662c.

Authors

Gajanan K Dewkar¹, Pedro B Carneiro, Matthew C T Hartman

Affiliation

¹ Department of Chemistry and Massey Cancer Center, Virginia Commonwealth University, 401 College Street, Richmond, Virginia 23298-0037, USA.

PMID: 19736915
DOI: 10.1021/ol901662c

Abstract

Synthesis of novel peptide linkers was accomplished by monocarboxylation of 1,3,5-tris(bomomethyl)benzene with a wide variety of carboxylic acids in the presence of diisopropylethylamine. These reagents can be used to simultaneously cyclize and label peptides containing two cysteines. Many labels are compatible with this method including lipids, fluorescent groups, and biotin.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Cyclization
Peptides / chemistry*
Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
Staining and Labeling
Time Factors
Xylenes / chemistry

Substances

Peptides
Xylenes