Synthesis of a conformationally constrained δ-amino acid building block

Amino Acids. 2013 Feb;44(2):511-8. doi: 10.1007/s00726-012-1362-3. Epub 2012 Aug 1.

Abstract

Conformationally restricted amino acids are important components in peptidomimetics and drug design. Herein, we describe the synthesis of a novel, non-proteinogenic constrained delta amino acid containing a cyclobutane ring, cis-3(aminomethyl)cyclobutane carboxylic acid (ACCA). The synthesis of the target amino acid was achieved in seven steps, with the key reaction being a base induced intramolecular nucleophilic substitution. A small library of dipeptides was prepared through the coupling of ACCA with proteinogenic amino acids.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemical synthesis*
  • Amino Acids / chemistry
  • Carboxylic Acids / chemistry
  • Cyclobutanes / chemistry
  • Molecular Structure

Substances

  • Amino Acids
  • Carboxylic Acids
  • Cyclobutanes