Convenient synthesis of collagen-related tripeptides for segment condensation

Biopolymers. 2015 Nov;104(6):674-81. doi: 10.1002/bip.22700.

Abstract

Chromatography is a common step in the solution-phase synthesis of typical peptides, as well as peptide fragments for subsequent coupling on a solid support. Combining known reagents that form readily separable byproducts is shown to eliminate this step, which wastes time and other resources. Specifically, activating carboxyl groups with isobutyl chloroformate or as pentafluorophenyl esters and using N-methyl morpholine as a base enable chromatography-free synthetic routes in which peptide products are isolated from byproducts by facile evaporation, extraction, and trituration. This methodology was used to access tripeptides related to collagen, such as Fmoc-Pro-Pro-Gly-OH and Fmoc-Pro-Hyp(tBu)-Gly-OH, in a purity suitable for solid-phase segment condensation to form collagen mimetic peptides.

Keywords: collagen; isobutyl chloroformate; pentafluorophenyl ester; segment condensation; synthesis.

Publication types

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

MeSH terms

  • Chromatography, Liquid
  • Collagen / chemistry*
  • Mass Spectrometry
  • Oligopeptides / chemical synthesis*
  • Oligopeptides / chemistry

Substances

  • Oligopeptides
  • Collagen