Alkyl Formate Ester Synthesis by a Fungal Baeyer-Villiger Monooxygenase

被引：17

作者：

Ferroni, Felix Martin ^{[1
]}

Tolmie, Carmien ^{[1
]}

Smit, Martha Sophia ^{[1
]}

Opperman, Diederik Johannes ^{[1
]}

机构：

[1] Univ Free State, Dept Biotechnol, 205 Nelson Mandela Dr, ZA-9300 Bloemfontein, South Africa

来源：

CHEMBIOCHEM | 2017年 / 18卷 / 06期

基金：

新加坡国家研究基金会;

关键词：

aldehydes; alkyl formate; Baeyer-Villiger monooxygenase; biocatalysis; formate ester; CYCLOHEXANONE MONOOXYGENASE; 4-HYDROXYACETOPHENONE MONOOXYGENASE; SUBSTRATE-SPECIFICITY; OXIDATION; TRANSESTERIFICATION; ENANTIOSELECTIVITY; REGIOSELECTIVITY; CHEMISTRY; SULFIDES; ALCOHOLS;

D O I：

10.1002/cbic.201600684

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

We investigated Baeyer-Villiger monooxygenase (BVMO)-mediated synthesis of alkyl formate esters, which are important flavor and fragrance products. A recombinant fungal BVMO from Aspergillus flavus was found to transform a selection of aliphatic aldehydes into alkyl formates with high regioselectivity. Near complete conversion of 10mm octanal was achieved within 8h with a regiomeric excess of approximate to 80%. Substrate concentration was found to affect specific activity and regioselectivity of the BVMO, as well as the rate of product autohydrolysis to the primary alcohol. More than 80% conversion of 50mm octanal was reached after 72h (TTN nearly 20000). Biotransformation on a 200mL scale under unoptimized conditions gave a space-time yield (STY) of 4.2gL(-1)d(-1) (3.4gL(-1)d(-1) extracted product).

引用

页码：515 / 517

页数：3

共 26 条

[1] Switching the Regioselectivity of a Cyclohexanone Monooxygenase toward (+)-trans-Dihydrocarvone by Rational Protein Design [J].