title: Marine fungi Aspergillus sydowii and Trichoderma sp. catalyze the hydrolysis of benzyl glycidyl ether.
abstract: Whole cells of the marine fungi Aspergillus sydowii Gc12, Penicillium raistrickii Ce16, P. miczynskii Gc5, and Trichoderma sp. Gc1, isolated from marine sponges of the South Atlantic Ocean (Brazil), have been screened for the enzymatic resolution of (±)-2-(benzyloxymethyl)oxirane (benzyl glycidyl ether; 1). Whole cells of A. sydowii Gc12 catalyzed the enzymatic hydrolysis of (R,S)-1 to yield (R)-1 with an enantiomeric excess (ee) of 24-46% and 3-(benzyloxy)propane-1,2-diol (2) with ee values <10%. In contrast, whole cells of Trichoderma sp. Gc1 afforded (S)-1 with ee values up to 60% and yields up to 39%, together with (R)-2 in 25% yield and an ee of 32%. This is the first published example of the hydrolysis of 1 by whole cells of marine fungi isolated from the South Atlantic Ocean. The hydrolases from the two studied fungi exhibited complementary regioselectivity in opening the epoxide ring of racemic 1, with those of A. sydowii Gc12 showing an (S) preference and those of Trichoderma sp. Gc1 presenting an (R) preference for the substrate.
authors.affiliation: Instituto de Química de São Carlos, Universidade de São Paulo, Av. Trabalhador, São-carlense, 400, CEP 13560-970 CP 780, São Carlos, São Paulo, Brazil.
authors.forename: Mariana Provedel
authors.initials: MP
authors.lastname: Martins
authors.forename: Ana Maria
authors.initials: AM
authors.lastname: Mouad
authors.forename: Letícia
authors.initials: L
authors.lastname: Boschini
authors.forename: Mirna Helena
authors.initials: MH
authors.lastname: Regali Seleghim
authors.forename: Lara Durães
authors.initials: LD
authors.lastname: Sette
authors.forename: André Luiz
authors.initials: AL
authors.lastname: Meleiro Porto
mesh_terms: D000098:Acetophenones / Q000737:chemistry / Q000378:metabolism; D001230:Aspergillus / Q000302:isolation & purification / Q000378:metabolism*; D001711:Biotransformation; D004202:Disinfectants / Q000737:chemistry / Q000378:metabolism*; D005027:Ethylene Oxide / Q000737:chemistry / Q000378:metabolism*; D006868:Hydrolysis; D014242:Trichoderma / Q000302:isolation & purification / Q000378:metabolism*; D014871:Water Microbiology; D014874:Water Pollutants, Chemical / Q000737:chemistry / Q000378:metabolism*
chemical_list: D000098:Acetophenones; D004202:Disinfectants; D014874:Water Pollutants, Chemical; D005027:Ethylene Oxide