Enzymatic synthesis of β-lactam antibiotics and N-fatty-acylated amino compounds by the acyl-transfer reaction catalyzed by penicillin V acylase from Streptomyces mobaraensis

Mayuko Koreishi, Kazuha Tani, Yuuichi Ise, Hiroyuki Imanaka, Koreyoshi Imamura, Kazuhiro Nakanishi

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

Penicillin V acylase from Streptomyces mobaraensis (Sm-PVA) showed high acyl-transfer activity in reactions using methyl esters of carboxylic acid (acyl donor) and amino compounds (nucleophile), to produce the corresponding amides. Moreover, Sm-PVA had broad substrate specificity, as indicated by the fact that it catalyzed the efficient synthesis of β-lactam antibiotics, capsaicin derivatives, and N-fatty-acyl-amino acid/N-fatty-acyl-peptide derivatives.

Original languageEnglish
Pages (from-to)1582-1586
Number of pages5
JournalBioscience, Biotechnology and Biochemistry
Volume71
Issue number6
DOIs
Publication statusPublished - 2007

Fingerprint

Streptomyces mobaraensis
penicillin V
Penicillin Amidase
lactams
amino compounds
Lactams
Capsaicin
Streptomyces
Antibiotics
Substrate Specificity
Carboxylic Acids
Amides
Esters
chemical derivatives
antibiotics
Anti-Bacterial Agents
Derivatives
Amino Acids
Peptides
Nucleophiles

Keywords

  • β-lactam antibiotics
  • Acyl transfer reaction
  • N-fatty-acylated amino compounds
  • Penicillin V acylase
  • Streptomyces mobaraensis

ASJC Scopus subject areas

  • Bioengineering
  • Biotechnology
  • Biochemistry
  • Biochemistry, Genetics and Molecular Biology(all)
  • Chemistry (miscellaneous)
  • Applied Microbiology and Biotechnology
  • Food Science

Cite this

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abstract = "Penicillin V acylase from Streptomyces mobaraensis (Sm-PVA) showed high acyl-transfer activity in reactions using methyl esters of carboxylic acid (acyl donor) and amino compounds (nucleophile), to produce the corresponding amides. Moreover, Sm-PVA had broad substrate specificity, as indicated by the fact that it catalyzed the efficient synthesis of β-lactam antibiotics, capsaicin derivatives, and N-fatty-acyl-amino acid/N-fatty-acyl-peptide derivatives.",
keywords = "β-lactam antibiotics, Acyl transfer reaction, N-fatty-acylated amino compounds, Penicillin V acylase, Streptomyces mobaraensis",
author = "Mayuko Koreishi and Kazuha Tani and Yuuichi Ise and Hiroyuki Imanaka and Koreyoshi Imamura and Kazuhiro Nakanishi",
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T1 - Enzymatic synthesis of β-lactam antibiotics and N-fatty-acylated amino compounds by the acyl-transfer reaction catalyzed by penicillin V acylase from Streptomyces mobaraensis

AU - Koreishi, Mayuko

AU - Tani, Kazuha

AU - Ise, Yuuichi

AU - Imanaka, Hiroyuki

AU - Imamura, Koreyoshi

AU - Nakanishi, Kazuhiro

PY - 2007

Y1 - 2007

N2 - Penicillin V acylase from Streptomyces mobaraensis (Sm-PVA) showed high acyl-transfer activity in reactions using methyl esters of carboxylic acid (acyl donor) and amino compounds (nucleophile), to produce the corresponding amides. Moreover, Sm-PVA had broad substrate specificity, as indicated by the fact that it catalyzed the efficient synthesis of β-lactam antibiotics, capsaicin derivatives, and N-fatty-acyl-amino acid/N-fatty-acyl-peptide derivatives.

AB - Penicillin V acylase from Streptomyces mobaraensis (Sm-PVA) showed high acyl-transfer activity in reactions using methyl esters of carboxylic acid (acyl donor) and amino compounds (nucleophile), to produce the corresponding amides. Moreover, Sm-PVA had broad substrate specificity, as indicated by the fact that it catalyzed the efficient synthesis of β-lactam antibiotics, capsaicin derivatives, and N-fatty-acyl-amino acid/N-fatty-acyl-peptide derivatives.

KW - β-lactam antibiotics

KW - Acyl transfer reaction

KW - N-fatty-acylated amino compounds

KW - Penicillin V acylase

KW - Streptomyces mobaraensis

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