Efficient chemoenzymatic synthesis of enantiomerically pure α-amino acids

Matthias Beller, Markus Eckert, Holger Geissler, Bernd Napierski, Heinz Peter Rebenstock, E. Wolfgang Holla

Research output: Contribution to journalArticlepeer-review

52 Scopus citations

Abstract

A general two-step chemoenzymatic synthesis for enantiomerically pure natural and nonnatural α-amino acids is presented. In the first step of the sequence, the ubiquitous educts aldehyde, amide and carbon monoxide react by palladium-catalyzed amidocarbonylation to afford the racemic N-acyl amino acids in excellent yields. In the second step, enzymatic enantioselective hydrolysis yields the free optically pure a-amino acid and the other enantiomer as the N-acyl derivative, both in optical purities of 85-99.5% ee. The advantage of the chemoenzymatic process compared to other amino acid synthesis are demonstrated by the preparation of various functionalized (-OR, -Cl, -F, -SR) α-amino acids on a 10-g scale.

Original languageEnglish
Pages (from-to)935-941
Number of pages7
JournalChemistry - A European Journal
Volume4
Issue number5
DOIs
StatePublished - 1998
Externally publishedYes

Keywords

  • Amido-carbonylation
  • Amino acids
  • Enzymes
  • Homogeneous catalysis
  • Palladium

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