3-Thiopropionic acid as a highly versatile multidetachable thioester resin linker

Julio A. Camarero, Alberto Adeva, Tom W. Muir

Research output: Contribution to journalArticlepeer-review

35 Scopus citations

Abstract

This paper describes a practical new use of 3-mercaptopropionic acid as a highly versatile multidetachable linker for solid-phase synthesis. Our approach is based on the stability of the alkylthioester functionality to optimized Boc-SPPS protocols and HF treatment, as well as on the mild activation of the thioester functionality toward nucleophilic or reductive displacement. This allows several C-terminal modifications to be introduced into a synthetic molecule during the cleavage step. We have shown that unprotected peptides can be efficiently cleaved from a propyl thioester- polyethylene glycol-poly-(N, N-dimethylacrylamide) copolymer resin using a great variety of nucleophiles to give the corresponding C-terminally modified peptides (esters, thioesters, carboxylic acids, thioacids, amides, hydroxamic acids, hydrazides, alcohols). The nucleophilic cleavage reaction is both rapid and exceptionally clean in all the cases tested.

Original languageEnglish (US)
Pages (from-to)17-21
Number of pages5
JournalLetters in Peptide Science
Volume7
Issue number1
DOIs
StatePublished - Jan 1 2000
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry

Keywords

  • C-terminal modified peptides
  • Hydrazides
  • Hydroxamates
  • Multidetachable resin
  • Solid-phase peptide synthesis
  • Thioester handle

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