A novel acylase from Streptomyces mobaraensis that efficiently catalyzes hydrolysis/synthesis of capsaicins as well as N-acyl-L-amino acids and N-acyl-peptides

Mayuko Koreishi, Demin Zhang, Hiroyuki Imanaka, Koreyoshi Imamura, Shuji Adachi, Ryuichi Matsuno, Kazuhiro Nakanishi

Research output: Contribution to journalArticlepeer-review

19 Citations (Scopus)

Abstract

A novel enzyme that catalyzes efficient hydrolysis of capsaicin (8-methyl-N-vanillyl-6-nonenamide) was isolated from the culture broth of Streptomyces mobaraensis. The enzyme consisted of two dissimilar subunits with molecular masses of 61 and 19 KDa. The enzyme was activated and stabilized in the presence of Co2+. It showed a pH optimum of about 8 and was stable at temperatures of up to 55°C for 1 h at pH 7.8. The specific activity of the enzyme for the hydrolysis of capsaicin was 10 2-104 times higher than those for the enzymes reported to date. In an aqueous/n-hexane biphasic system, capsaicin analogues such as octanoyl, decanoyl, and lauroyl vanillylamides were synthesized from the corresponding fatty acids and vanillylamine at yields of 50% or greater. In addition, the enzyme catalyzed the deacylation of N-lauroyl-L-amino acids and N-lauroyl-L-dipeptides and the efficient synthesis of Nα-lauroyl-L-lysine, Nε-lauroyl-L-lysine, and various N-lauroyl-peptides in aqueous solution in both the absence and the presence of glycerol.

Original languageEnglish
Pages (from-to)72-78
Number of pages7
JournalJournal of agricultural and food chemistry
Volume54
Issue number1
DOIs
Publication statusPublished - Jan 11 2006

Keywords

  • Actinomycetes
  • Capsaicin
  • Capsaicin derivative
  • Lauric acid
  • N-acyl-L-amino acid
  • N-acyl-peptide
  • Streptomyces mobaraensis

ASJC Scopus subject areas

  • Chemistry(all)
  • Agricultural and Biological Sciences(all)

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