Marine fungi Aspergillus sydowii and Trichoderma sp. catalyze the hydrolysis of benzyl glycidyl ether.
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.
Martins
Mariana Provedel
MP
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.
Mouad
Ana Maria
AM
Boschini
Letícia
L
Regali Seleghim
Mirna Helena
MH
Sette
Lara Durães
LD
Meleiro Porto
André Luiz
AL
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*
D000098:Acetophenones; D004202:Disinfectants; D014874:Water Pollutants, Chemical; D005027:Ethylene Oxide