A rapid and clean synthetic approach to cyclic peptides via micro-flow peptide chain elongation and photochemical cyclization: synthesis of a cyclic RGD peptide

Yuto Mifune; Hiroyuki Nakamura; Shinichiro Fuse

doi:10.1039/c6ob02391f

A rapid and clean synthetic approach to cyclic peptides via micro-flow peptide chain elongation and photochemical cyclization: synthesis of a cyclic RGD peptide

Org Biomol Chem. 2016 Nov 29;14(47):11244-11249. doi: 10.1039/c6ob02391f.

Authors

Yuto Mifune¹, Hiroyuki Nakamura¹, Shinichiro Fuse¹

Affiliation

¹ Laboratory for Chemistry and Life Science, Institute of Innovative Research, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8503, Japan. sfuse@res.titech.ac.jp.

PMID: 27849093
DOI: 10.1039/c6ob02391f

Abstract

A cyclic RGD peptide was efficiently synthesized based on micro-flow, triphosgene-mediated peptide chain elongation and micro-flow photochemical macrolactamization. Our approach enabled a rapid (amidation for peptide chain elongation <5 s, macrolactamization <5 min) and clean (only one column chromatographic separation) synthesis of a cyclic peptide.

MeSH terms

Chemistry Techniques, Synthetic / methods*
Green Chemistry Technology
Integrin alphaVbeta3 / antagonists & inhibitors
Kinetics
Peptides, Cyclic / chemical synthesis*
Peptides, Cyclic / chemistry*
Peptides, Cyclic / pharmacology
Photochemical Processes*

Substances

Integrin alphaVbeta3
Peptides, Cyclic
cyclic arginine-glycine-aspartic acid peptide