Synthesis of cyclic, multivalent Arg-Gly-Asp using sequential thiol-ene/thiol-yne photoreactions

Alex A Aimetti; Kristen R Feaver; Kristi S Anseth

doi:10.1039/c0cc01292k

Synthesis of cyclic, multivalent Arg-Gly-Asp using sequential thiol-ene/thiol-yne photoreactions

Chem Commun (Camb). 2010 Aug 21;46(31):5781-3. doi: 10.1039/c0cc01292k. Epub 2010 Jun 15.

Authors

Alex A Aimetti¹, Kristen R Feaver, Kristi S Anseth

Affiliation

¹ Department of Chemical & Biological Engineering, University of Colorado, Boulder, CO 80309, USA.

Abstract

A unique method has been developed for the formation of multivalent cyclic peptides. This procedure exploits on-resin peptide cyclization using a photoinitiated thiol-ene click reaction and subsequent clustering using thiol-yne photochemistry. Both reactions utilize the sulfhydryl group on natural cysteine amino acids to participate in the thiol-mediated reactions.

Publication types

Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Oligopeptides / chemistry*
Peptides, Cyclic / chemical synthesis*
Peptides, Cyclic / chemistry
Photochemical Processes
Sulfhydryl Compounds / chemistry*

Substances

Oligopeptides
Peptides, Cyclic
Sulfhydryl Compounds
arginyl-glycyl-aspartic acid

Abstract

Publication types

MeSH terms

Substances

Grants and funding