Application of Threonine Aldolases for the Asymmetric Synthesis of α-Quaternary α-Amino Acids

Julia Blesl, Melanie Trobe, Felix Anderl, Rolf Breinbauer, Gernot A. Strohmeier, Kateryna Fesko*

*Korrespondierende/r Autor/in für diese Arbeit

Publikation: Beitrag in einer FachzeitschriftArtikel

Abstract

We report the synthesis of diverse β-hydroxy-α,α-dialkyl-α-amino acids with perfect stereoselectivity for the α-quaternary center through the action of l- and d-specific threonine aldolases. A wide variety of aliphatic and aromatic aldehydes were accepted by the enzymes and conversions up to >80 % were obtained. In the case of d-selective threonine aldolase from Pseudomonas sp., generally higher diastereoselectivities were observed. The applicability of the protocol was demonstrated by performing enzymatic reactions on preparative scale. Using the d-threonine aldolase from Pseudomonas sp., (2R,3S)-2-amino-3-(2-fluorophenyl)-3-hydroxy-2-methylpropanoic acid was generated in preparative amounts in one step with a diastereomeric ratio >100 favoring the syn-product. A Birch-type reduction enabled the reductive removal of the β-hydroxy group from (2S)-2-amino-3-hydroxy-2-methyl-3-phenylpropanoic acid to generate enantiopure l-α-methyl-phenylalanine via a two-step chemo-enzymatic transformation.

Originalspracheenglisch
Seiten (von - bis)3453-3458
Seitenumfang6
FachzeitschriftChemCatChem
Jahrgang10
Ausgabenummer16
DOIs
PublikationsstatusVeröffentlicht - 21 Aug 2018

ASJC Scopus subject areas

  • !!Catalysis
  • Organische Chemie

Fields of Expertise

  • Human- & Biotechnology

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