Synthesis of γ-halogenated and long-chain β-hydroxy-α-amino acids and 2-amino-1,3-diols using threonine aldolases

Johannes Steinreiber, Kateryna Fesko, Clemens Mayer, Christoph Reisinger, Martin Schürmann, Herfried Griengl*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

45 Citations (Scopus)

Abstract

The L- and D-threonine aldolase catalyzed formation of γ-halogenated and long-chain L- and D-3-alkylserine-derivatives 1–12, respectively, was shown starting from glycine and halogenated C2– or C4–C12 aldehydes. LTA from Pseudomonas putida accepted all tested aldehydes with strongly varying diastereoselectivity (de up to 93%). Only aldehydes smaller than decanal were converted by DTA from Alcaligenes xylosoxidans with good selectivities (de up to 73%). Utilizing isobutanal enantio- and diastereopure d-syn-2-amino-3-hydroxy-4-methylpentanoic acid was obtained (ee>99%, de>95%), which was converted to the corresponding 2-amino-1,3-diol.
Original languageEnglish
Pages (from-to)8088-8093
JournalTetrahedron
Volume63
Issue number34
DOIs
Publication statusPublished - 9-Jun-2007
Externally publishedYes

Keywords

  • Enzymes
  • Threonine aldolase
  • Biocatalysis
  • Amino acid

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