title: Synthesis of a conformationally constrained δ-amino acid building block.
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.
authors.affiliation: Centre for Synthesis and Chemical Biology, UCD School of Chemistry and Chemical Biology, Belfield, Dublin 4, Ireland.
authors.forename: Elaine
authors.initials: E
authors.lastname: O'Reilly
authors.forename: Lara
authors.initials: L
authors.lastname: Pes
authors.forename: Yannick
authors.initials: Y
authors.lastname: Ortin
authors.forename: Helge
authors.initials: H
authors.lastname: Müller-Bunz
authors.forename: Francesca
authors.initials: F
authors.lastname: Paradisi
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry; D003503:Cyclobutanes / Q000737:chemistry; D015394:Molecular Structure
chemical_list: D000596:Amino Acids; D002264:Carboxylic Acids; D003503:Cyclobutanes