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. 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Microbial communities in an oligotrophic reservoir influenced by high levels of ionizing radiation

In this study, we investigated the microbial community (bacteria and protozooplankton) of a Brazilian reservoir that receives neutralized acid mine drainage flowing from piles of earth produced during uranium extraction. Thus, this research represents an attempt to fill a gap in the information on the ecology of freshwater microorganisms in tropical oligotrophic habitats, in particular in systems affected by high levels of the uranium. During the study, we observed very low chlorophyll a contents and protozooplankton cell densities and biomass. These cell densities were between 0 and 89 cells L−1 and were lower than those frequently reported for oligotrophic freshwater lakes. In contrast, bacterial densities were normal or even slightly high, between 1.85 to 6.0 × 109 cells L−1. The present study has demonstrated very low protozooplankton cell densities and biomass in oligotrophic reservoir under the influence of acidic mining effuents and of high levels of ionizing radiation. It is likely that the ciliate cell densities and biomasses recorded in this study, which fall significantly below the previously published values, can be explained by the chronic fractionated exposure of these protozoa to the high levels of uranium to this system

Bioreduction Of α-chloroacetophenone By Whole Cells Of Marine Fungi

The asymmetric reduction of 2-chloro-1-phenylethanone (1) by seven strains of marine fungi was evaluated and afforded (S)-(-)-2-chloro-1-phenylethanol with, in the best case, an enantiomeric excess of 50% and an isolated yield of 60%. The ability of marine fungi to catalyse the reduction was directly dependent on growth in artificial sea water-based medium containing a high concentration of Cl- (1.2 M). When fungi were grown in the absence of artificial sea water, no reduction of 1 by whole cells was observed. The biocatalytic reduction of 1 was more efficient at neutral rather than acidic pH values and in the absence of glucose as co-substrate. © 2009 Springer Science+Business Media B.V.311015591563Amidjojo, M., Weuster-Botz, D., Asymmetric synthesis of the chiral synthon ethyl (S)-4-chloro-3-hydroxybutanoate using Lactobacillus kefir (2005) Tetrahedron Asymm, 16, pp. 899-901Assumpção, R.M.V., Morita, T., Manual de soluções, reagentes e solvents, , 2nd edn. 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(2007) Curr Opin Chem Biol, 11, pp. 553-560Goswami, A., Mirfakhrae, K.D., Totleben, M.J., Swaminathan, S., Patel, R.N., Microbial reduction of α-chloroketone to α-chlorohydrin (2001) J Ind Microbiol Biotechnol, 26, pp. 259-262Groger, H., Hummel, W., Rollmann, C., Chamouleau, F., Husken, H., Werner, H., Wunderlich, C., Buchholz, S., Preparative asymmetric reduction of ketones in a biphasic medium with an (S)-alcohol dehydrogenase under in situ-cofactor-recycling with a formate dehydrogenase (2004) Tetrahedron, 60, pp. 633-640Hunt, B., Vincent, A.C.J., Scale and sustainability of marine bioprospecting for pharmaceuticals (2006) Ambio, 35, pp. 57-64Itoh, N., Matsuda, M., Mabuchi, M., Dairi, T., Wang, J., Chiral alcohol production by NADH-dependent phenylacetaldehyde reductase coupled with in situ regeneration of NADH (2002) Eur J Biochem, 269, pp. 2394-2402Mayer, A.M.S., Rodríguez, A.D., Berlinck, R.G.S., Hamann, M.T., Marine pharmacology in 2003-4: Marine compounds with antihelmintic antibacterial, anticoagulant, antifungal, anti-inflammatory, antimalarial, antiplatelet, antiprotozoal, antituberculosis, and antiviral activitiesaffecting the cardiovascular, immune and nervous systems, and other miscellaneous mechanisms of action (2007) Comp Biochem Physiol C, 145, pp. 553-581Pavia, D.L., Lampman, G.M., Kriz, G.S., Engel, R.G., (1999) Introduction to Organic Laboratory Techniques, , 3rd edn. Sunders College Publishing, OrlandoPiovan, L., Capelari, M., Andrade, L.H., Comasseto, J.V., Porto, A.L.M., Biocatalytic reduction of a racemic selenocyclohexanone by Brazilian basidiomycetes (2007) Tetrahedron Asymm, 18, pp. 1398-1402Pollard, D.J., Woodley, J.M., Biocatalysis for pharmaceutical intermediates: The future is now (2006) Trends Biotechnol, 25, pp. 66-73Ricci, 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. 937-946Tanis, S.P., Evans, B.R., Nieman, J.A., Parker, T.T., Taylor, W.D., Heasley, S.E., Herrinton, P.M., Seest, E.P., Solvent and in situ catalyst preparation impacts upon Noyori reductions of aryl-chloromethyl ketones: Application to syntheses of chiral 2-amino-1-aryl-ethanols (2006) Tetrahedron Asymm, 17, pp. 2154-2182Vaillancourt, F.H., Yeh, E., Vosburg, D.A., Garneau-Tsodikova, S., Walsh, C.T., Nature's inventory of halogenation catalysts: Oxidative strategies predominate (2006) Chem Rev, 106, pp. 3364-3378Wei, Z.-L., Li, Z.-Y., Lin, G.-Q., Anti-Prelog microbial reduction of aryl α-halomethyl or α-hydroxymethyl ketones with Geotrichum sp 38 (1998) Tetrahedron, 54, pp. 13059-13072Zhao, H., van der Donk, W.A., Regeneration of cofactors for use in biocatalysis (2003) Curr Opin Biotechnol, 14, pp. 583-589Zhu, D., Rios, B.E., Rozzell, J.D., Hua, L., Evaluation of substituent effects on activity and enantioselectivity in the enzymatic reduction of aryl ketones (2005) Tetrahedron Asymm, 16, pp. 1541-154