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Applied Microbiology and Biotechnology

, Volume 48, Issue 4, pp 546-548

Novel l-specific cleavage of the urethane bond of t -butoxycarbonylamino acids by whole cells of Corynebacterium aquaticum

  • T. OhshiroAffiliated withDepartment of Biotechnology, Tottori University, Tottori 680, Japan Tel.: 81 857 31 5267; Fax.: 81 857 31 5267
  • , M. ShinjiAffiliated withDepartment of Biotechnology, Tottori University, Tottori 680, Japan Tel.: 81 857 31 5267; Fax.: 81 857 31 5267
  • , Y. MoritaAffiliated withDepartment of Biotechnology, Tottori University, Tottori 680, Japan Tel.: 81 857 31 5267; Fax.: 81 857 31 5267
  • , Y. TakayamaAffiliated withDepartment of Biotechnology, Tottori University, Tottori 680, Japan Tel.: 81 857 31 5267; Fax.: 81 857 31 5267
  • , Y. IzumiAffiliated withDepartment of Biotechnology, Tottori University, Tottori 680, Japan Tel.: 81 857 31 5267; Fax.: 81 857 31 5267

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Abstract

Microorganisms capable of cleaving the urethane bond of t-butoxycarbonyl (Boc) amino acids in a whole-cell reaction were screened among stock cultures, and Corynebacterium aquaticum IFO12154 was the most promising. The conversion of Boc-Ala to Ala was stimulated by CoSO4 in the medium and reaction mixture. The optimum whole-cell concentration was 25 mg lyophilized cells/ml. Boc-l-Met was the best substrate for this reaction, and other Boc-L-amino acids, as well as benzyloxycarbonyl-l-amino acids with hydrophobic residues, were also good substrates. Boc-d- and Z-d-amino acids were inert. When the reactions had proceeded for 24 h with each substrate at 10 mM, the molar conversion rates from Boc-l-, dl- and d-Met were 100%, 50%, and 0% respectively. From 150 mM Boc-l-Met, 143 mM l-Met was formed at a molar yield of 95.3%.