Enantioselective synthesis of an unnatural bipyridyl amino acid and its incorporation into a peptide

Kenneth J. Kise, Bruce E. Bowler

Research output: Contribution to journalArticlepeer-review

Abstract

The synthesis of a bipyridyl amino acid, 2-amino-3-(4'-methyl-2,2'- bipyridin-4-yl) propanoic acid, is described. A short three step synthesis from commercially available 4,4'-dimethyl-2,2'-bipyridine provides the amino acid in 65% enantiomeric excess (ee). An enzyme-mediated chiral resolution increases the ee to 95% in two additional steps. The amino acid was incorporated into a 22 amino acid peptide composed predominantly of alanine. The peptide was found to be 88% α-helical in aqueous solution at 1°C by circular dichroism (CD) spectropolarimetry, indicating a high helical propensity for this amino acid. This amino acid can provide a means to incorporate a metal into structure-forming peptides.

Original languageEnglish
Pages (from-to)3319-3324
Number of pages6
JournalTetrahedron Asymmetry
Volume9
Issue number18
DOIs
StatePublished - Sep 18 1998

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