title: Alkyl Formate Ester Synthesis by a Fungal Baeyer-Villiger Monooxygenase.
abstract: 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 10 mm octanal was achieved within 8 h with a regiomeric excess of ∼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 50 mm octanal was reached after 72 h (TTN nearly 20 000). Biotransformation on a 200 mL scale under unoptimized conditions gave a space-time yield (STY) of 4.2 g L-1d-1(3.4 g L-1d-1extracted product).
authors.affiliation: Department of Biotechnology, University of the Free State, 205 Nelson Mandela Drive, Bloemfontein, 9300, South Africa.
authors.forename: Felix Martin
authors.initials: FM
authors.lastname: Ferroni
authors.affiliation: Department of Biotechnology, University of the Free State, 205 Nelson Mandela Drive, Bloemfontein, 9300, South Africa.
authors.forename: Carmien
authors.initials: C
authors.lastname: Tolmie
authors.affiliation: Department of Biotechnology, University of the Free State, 205 Nelson Mandela Drive, Bloemfontein, 9300, South Africa.
authors.forename: Martha Sophia
authors.initials: MS
authors.lastname: Smit
authors.affiliation: Department of Biotechnology, University of the Free State, 205 Nelson Mandela Drive, Bloemfontein, 9300, South Africa.
authors.forename: Diederik Johannes
authors.initials: DJ
authors.lastname: Opperman
mesh_terms: D000438:Alcohols / Q000378:metabolism; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D005561:Formates / Q000138:chemical synthesis* / Q000737:chemistry; D005658:Fungi / Q000201:enzymology; D006899:Mixed Function Oxygenases / Q000737:chemistry / Q000378:metabolism*; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D004952:Esters; D005561:Formates; D006899:Mixed Function Oxygenases
keywords: Baeyer-Villiger monooxygenase; aldehydes; alkyl formate; biocatalysis; formate ester