A Selective Deprotection Strategy for the Construction of trans-2-Aminocyclopropanecarboxylic Acid Derived Peptides

Org Lett. 2019 Jan 4;21(1):100-103. doi: 10.1021/acs.orglett.8b03533. Epub 2018 Dec 17.

Abstract

A procedure allowing access to unprecedented tripeptides containing a trans-2-aminocyclopropanecarboxylic acid residue in their central position has been established. The key features of the strategy are the use of a masked trans-2-aminocyclopropanecarboxylic acid monomer equivalent for C-terminal coupling and full N-Boc protection of all amide groups until the final step.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carboxylic Acids / chemistry*
  • Crystallography, X-Ray
  • Cyclopropanes / chemistry*
  • Models, Molecular
  • Molecular Structure
  • Peptides / chemical synthesis*
  • Peptides / chemistry

Substances

  • 2-aminomethylcyclopropanecarboxylic acid
  • Carboxylic Acids
  • Cyclopropanes
  • Peptides