Article

Synthesis of a conformationally constrained δ-amino acid building block.

Centre for Synthesis and Chemical Biology, UCD School of Chemistry and Chemical Biology, Belfield, Dublin 4, Ireland.
Amino Acids (impact factor: 3.25). 08/2012; DOI:10.1007/s00726-012-1362-3
Source: PubMed

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.

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Keywords

amino acids
 
base induced intramolecular nucleophilic substitution
 
cis-3(aminomethyl)cyclobutane carboxylic acid
 
cyclobutane ring
 
dipeptides
 
drug design
 
key reaction
 
non-proteinogenic constrained delta amino acid
 
proteinogenic amino acids
 
small library
 
steps
 
target amino acid