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Engineering of the Cytochrome P450 Monooxygenase System for Benzyl Maltol Hydroxylation

Engineering of the Cytochrome P450 Monooxygenase System for Benzyl Maltol Hydroxylation

Iori Kozono, Kousuke Mihara, Kazuyuki Minagawa, Makoto Hibi, Jun Ogawa

Appl Microbiol Biotechnol. 2017 Sep;101(17):6651-6658.

PMID: 28730410

Abstract:

Maltol derivatives are utilized in a variety of fields due to their metal-chelating abilities, and modification of the 2-methyl side chain is known to effectively expand their functional diversity. In the present study, microbial enzymes were screened for hydroxylating activity towards the 2-methyl group in a maltol derivative, 3-benzyloxy-2-methyl-4-pyrone (BMAL). Novosphingobium sp. SB32149 was found to have the ability to convert BMAL into 3-benzyloxy-2-hydroxymethyl-4-pyrone (BMAL-OH). The enzymes responsible, a cytochrome P450 monooxygenase (P450nov), a ferredoxin (FDXnov), and a ferredoxin reductase (FDRnov), were identified in the SB32149 strain. In the reaction with recombinant Escherichia coli expressing P450nov, FDXnov, and FDRnov, BMAL-OH was successfully produced from BMAL. Moreover, using the directed evolution approach, four amino acid substitutions, L188P/F218L/L237M in P450nov and A10T in FDXnov, were found to enhance BMAL-OH production. Consequently, up to 5.2 g/L BMAL-OH was obtained from 8.0 g/L BMAL by bioconversion using a 250-mL jar fermenter, indicating that this strain may be useful for synthesis of maltol derivatives which could have potential applications in various fields.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP870718073	3-Benzyloxy-2,6-difluorophenylboronic acid		870718-07-3	Price

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