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. © 2010 Springer Science+Business Media, LLC.132314320Handbook of fine chemicals (2006) Acros Organics, Geel, , Acros Organics, BelgiumAssis, L.F., Kagohara, E., Omori, A.T., Comasseto, J.V., Andrade, L.H., Porto, A.L.M., Deracemization of (RS)-1-[(4-methylselanyl)phenyl]ethanol and (RS)-1-[(4-ethylselanyl)phenyl]ethanol by strains of Aspergillus terreus (2007) Food Technol Biotechnol, 45, pp. 415-419Bommarius, A.S., Riebel, B.R., (2004) Biocatalysis: Fundamentals and Applications, , 1st edn., Atlanta: Wiley-VCHBonugli-Santos, R.C., Durrant, L.R., da Silva, M., Sette, L.D., Production of laccase, manganese peroxidase and lignin peroxidase by Brazilian marine-derived fungi (2010) Enzyme Microb Technol, 46, pp. 32-37Botes, A.L., Weijers, C.A.G.M., Botes, P.J., van Dyk, M.S., Enantioselectivities of yeast epoxide hydrolases for 1,2-epoxides (1999) Tetrahedron: Asymmetry, 10, pp. 3327-3336Bredikhina, Z.A., Akhatova, F.S., Zakharychev, D.V., Bredikhin, A.A., Spontaneous resolution amongst chiral ortho-cyanophenyl glycerol derivatives: an effective preferential crystallization approach to a single enantiomer of the β-adrenoblocker bunitrolol (2008) Tetrahedron Asymmetr, 19, pp. 1430-1435Caner, H., Groner, E., Levy, L., Agranat, I., Trends in the development of chiral drugs (2004) Drug Discov Today, 9, pp. 105-110Comasseto, J.V., Assis, L.F., Andrade, L.H., Schoenlein-Crusius, I.H., Porto, A.L.M., Biotransformations of ortho-, meta- and para-aromatic nitrocompounds by strains of Aspergillus terreus: Reduction of ketones and deracemization of alcohols (2006) J Mol Catal B Enzym, 39, pp. 24-30da Costa, C.E., Comasseto, J.V., Crusius, I.H.S., Andrade, L.H., Porto, A.L.M., Biotransformation of β-hydroxyphenyl selenides, diphenyldiselenide and benzeneseleninic acid by whole cells of Aspergillus terreus (2007) J Mol Catal B Enzym, 45, pp. 135-139Drapeau, G.R., Matula, T.I., Macleod, R.A., Nutrition and metabolism of marine bacteria1 XV. Relation of Na +-activated transport to the Na + requirement of a marine pseudomonad for growth (1966) J Bacteriol, 92, pp. 63-71Egri, G., Bálint, J., Peredi, R., Fogassy, E., Novák, L., Poppe, L., Lipase-catalyzed enantiotope selective acetylation of 2-acyloxypropane-1,3-diols. Influence of the acyl moiety on the selectivity (2000) J Mol Catal B: Enzym, 10, pp. 583-596Faber, K., (2004) Biotransformations in Organic Chemistry: A Textbook, , 5th edn., Berlin: SpringerFujino, A., Asano, M., Yamaguchi, H., Shirasaka, N., Sakoda, A., Ilkunaka, M., Obata, R., Sugai, T., Bacillus subtilis epoxide hydrolase-catalyzed preparations of enantiopure 2-methylprtopane-1,2,3-triol monobenzyl ether and its application to expeditions synthesis of (R)-bicalutamide (2007) Tetrahedron Lett, 48, pp. 979-983García-Arieta, A., Abad-Santos, F., Rodríguez-Martínez, M.A., Varas-Polo, Y., Novalbos, J., Laparidis, N., Gallego-Sandín, S., Torrado, J., An eutomer/distomer ratio near unity does not justify non-enantiospecific assay methods in bioequivalence studies (2005) Chirality, 17, pp. 470-475Gong, P.-F., Xu, J.-H., Bio-resolution of a chiral epoxide using whole cells of Bacillus megaterium ECU1001 in a biphasic system (2005) Enzyme Microbiol Technol, 36, pp. 252-257Kagohara, E., Pellizari, V.H., Comasseto, J.V., Andrade, L.H., Porto, A.L.M., Biotransformations of substituted phenylethanols and acetophenones by environmental bacteria (2008) Food Technol Biotechnol, 46, pp. 381-387Kamal, A., Chouhan, G., Chemoenzymatic synthesis of calcilytic agent NPS-2143 employing a lipase-mediated resolution protocol (2005) Tetrahedron Asymmetr, 16, pp. 2784-2789Kamal, A., Sandbhor, M., Shaik, A.A., Chemoenzymatic synthesis of (S) and (R)-propanolol and sotalol employing one-pot lipase resolution protocol (2004) Bioorg Med Chem Lett, 14, pp. 4581-4583Keppler, A.F., Porto, A.L.M., Schoenlein-Crusius, I.H., Comasseto, J.V., Andrade, L.H., Enzymatic evaluation of different Aspergillus strains by biotransformation of cyclic ketones (2005) Enzyme Microb Technol, 36, pp. 967-975Kogure, K., Bioenergetics of marine bacteria (1998) Curr Opin Biotechnol, 9, pp. 278-282Kotik, M., Brichac, J., Kyslík, P., Novel microbial epoxide hydrolases for biohydrolysis of glycidyl derivatives (2005) J Biotechnol, 120, pp. 364-375Macleod, R.A., The question of the existence of specific marine bacteria (1965) Bacteriol Rev, 29, pp. 9-23Maher, T.J., Johnson, D.A., Review of chirality and its importance in pharmacology (2004) Drug Dev Res, 24, pp. 149-156Mischitz, M., Kroutil, W., Wandel, U., Faber, K., Asymmetric microbial hydrolysis of epoxides (1995) Tetrahedron Asymmetr, 6, pp. 1261-1272Piovan, L., Capelari, M., Andrade, L.H., Comasseto, J.V., Porto, A.L.M., Biocatalytic reduction of a racemic selenocyclohexanone by Brazilian basidiomycetes (2007) Tetrahedron Asymmetr, 18, pp. 1398-1402Piovan, L., Kagohara, E., Ricci, L.C., Keppler, A.F., Capelari, M., Andrade, L.H., Comasseto, J.V., Porto, A.L.M., Chemoselective screening for the reduction of a chiral functionalised (+/-)-2-(phenylthio)cyclohexanone by whole cells of Brazilian micro-organisms (2008) Tetrahedron Asymmetr, 19, pp. 2385-2389Raminelli, C., Kagohara, E., Pellizari, V.H., Comasseto, J.V., Andrade, L.H., Porto, A.L.M., Biotransformations of Mannich bases and propiophenones by Brazilian microorganisms and enzymatic resolution of phenylpropanols by lipase from Candida antarctica (Novozym 435) (2007) Enzyme Microb Technol, 40, pp. 362-369Ricci, L.C., Comasseto, J.V., Andrade, L.H., Capelari, M., Cass, Q.B., Porto, A.L.M., Biotransformations of aryl alkyl sulfides by whole cells of white-rot Basidiomycetes (2005) Enzyme Microb Technol, 36, pp. 937-946Rocha, L.C., Ferreira, H.V., Pimenta, E.F., Berlinck, R.G.S., Seleghim, M.H.R., Javaroti, D.C.D., Sette, L.D., Porto, A.L.M., Bioreduction of alpha-chloroacetophenone by whole cells of marine fungi (2009) Biotechnol Lett, 31, pp. 1559-1563Rocha, L.C., Ferreira, H.V., Pimenta, E.F., Berlinck, R.G.S., Rezende, M.O.O., Landgraf, M.D., Seleghim, M.H.R., Porto, A.L.M., Biotransformation of α-bromoacetophenones by the marine fungus Aspergillus sydowii (2010) Marine Biotechnol, , doi: 10. 1007/s10126-009-9241-ySimeó, Y., Faber, K., Selectivity enhancement of enantio- and stereo-complementary epoxide hydrolases and chemo-enzymatic deracemization of (±)-2-methylglycidyl benzyl ether (2006) Tetrahedron Asymmetr, 17, pp. 402-409Steinrieber, A., Osprian, I., Mayer, S.F., Orru, R.V.A., Faber, K., Enantioselective hydrolysis of functionalized 2,2-disubstituted oxiranes with bacterial epoxide hydrolases (2000) Eur J Org Chem, 2000, pp. 3703-3711Sun, F., Xu, G., Wu, J., Yang, L., New and facile preparation of tert-butyl (3R, 5S)-6-hydroxy-3,5-O-isopropylidene-3,5-dihydroxyhexanoate (2007) Tetrahedron Asymmetr, 18, pp. 2454-2461van Loo, B., Kingma, J., Heyman, G., Wittenaar, A., Spelberg, J.H.L., Sonke, T., Janssen, D.B., Improved enantioselective conversion of styrene epoxides and meso-epoxides through epoxide hydrolases with a mutant nucleophilic-flanking residue (2009) Enzyme Microbiol Technol, 44, pp. 145-153Vogel, A.I., (1989) Textbook of Practical Organic Chemistry, , 5th edn., London: LongmansWeijers, C.A.G.M., Enantioselective hydrolysis of aryl, alicyclic and aliphatic epoxides by Rhodotorula glutinis (1997) Tetrahedron Asymmetr, 8, pp. 639-647Wood, E.J.F., (1967) Microbiology of Oceans and Estuaries. Elsevier Oceanographic Series 3, p. 319. , 2nd edn., Barking: ElsevierXu, Y., Xu, J.-H., Pan, J., Tang, Y.-F., Biocatalytic resolution of glycidyl aryl ethers by Trichosporon loubierii: cell/substrate ratio influences the optical purity of (R)-epoxides (2004) Biotechnol Lett, 26, pp. 1217-1221Xu, Y., Xu, J.-H., Pan, J., Zhao, L., Zhang, S.-L., Biocatalytic resolution of nitro-substituted phenoxypropylene oxides with Trichosporon loubierii epoxide hydrolase and prediction of their enantiopurity variation with reaction time (2004) J Mol Catal B Enzym, 27, pp. 155-159