Chemo- and stereoselective reduction of β-keto esters by spores and various morphological forms of Mucor rouxii
We report the efficient enantioselective reduction of a number of β-ketoesters by mycelial and yeast-like forms of the dimorphic fungus Mucor rouxii in a whole-cell process. Mycelial cells, grown in aerobiosis, were efficient in water, whereas the yeast-like cells, grown in anaerobic medium, were bo...
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2002
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| LEADER | 08954caa a22011777a 4500 | ||
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| 001 | PAPER-5358 | ||
| 003 | AR-BaUEN | ||
| 005 | 20230518203500.0 | ||
| 008 | 190411s2002 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-0037007547 | |
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 030 | |a EMTED | ||
| 100 | 1 | |a Mangone, C.P. | |
| 245 | 1 | 0 | |a Chemo- and stereoselective reduction of β-keto esters by spores and various morphological forms of Mucor rouxii |
| 260 | |c 2002 | ||
| 270 | 1 | 0 | |m Baldessari, A.; Departamento de Quimica Organica, Facultad Ciencias Exactas Naturales, Universidad de Buenos Aires, 1428 Buenos Aires, Argentina; email: alib@qo.fcen.uba.ar |
| 506 | |2 openaire |e Política editorial | ||
| 504 | |a Mori, K., Synthesis of optically active pheromones (1989) Tetrahedron, 45, pp. 3233-3298 | ||
| 504 | |a Soai, K., Takashi, Y., Hitoshi, H., Oyamada, H., Asymmetric reduction of prochiral 3-aryl-3-oxoesters with lithium borohydride using N,N′-dibenzoylcystine as a chiral auxiliary (1985) J Chem Soc Chem Commun, pp. 138-139 | ||
| 504 | |a Burk, M.J., Harper, T.G.P., Kalberg, C.S., Highly enantioselective hydrogenation of β-ketoesters under mild conditions (1995) J Am Chem Soc, 117, pp. 4223-4224 | ||
| 504 | |a Evans, D.A., Morrissey, M.M., Dorow, R.L., Asymmetric oxigenation of chiral imide enolates. A general approach to the synthesis of enantiomerically pure α-hydroxy carboxylic acid synthons (1985) J Am Chem Soc, 107, pp. 4346-4348 | ||
| 504 | |a Marcantoni, E., Alessandrini, S., Malavolta, M., Reverse stereochemical control in the presence of CeCl3 and TiCl4 in the Lewis acid mediated reduction of α-alkyl-β-ketoesters by metal hydrides. A general methodology for the diasteroselective synthesis of syn and anti α-alkyl-β-hydroxy esters (1999) J Org Chem, 64, pp. 1986-1992 | ||
| 504 | |a Sheldon, R.A., (1993) Chirotechnology, pp. 423-423. , New York: Dekker | ||
| 504 | |a Adam, W., Lazarus, M., Boss, B., Saha-Möller, C.R., Humpf, H.U., Schreier, P., Enzymatic resolution of chiral 2-hydroxy carboxylic acids by enantioselective oxidation with molecular oxygen catalyzed by the glycolate oxidase from spinach (Spinacia oleracea) (1997) J Org Chem, 62, pp. 7841-7843 | ||
| 504 | |a Wong, C.H., Whitesides, G.M., Oxidoreductions (1994) Enzymes in Synthetic Organic Chemistry, pp. 131-194. , Balwin, Magnus, editors. Oxford: Elsevier Science Ltd | ||
| 504 | |a Kitayama, T., Microbial asymmetric syntheses of 3-alkylphthalide derivatives (1997) Tetrahedron Asym, 22, pp. 3765-3774 | ||
| 504 | |a Panke, S., Wubbolts, M.G., Schmid, A., Withold, B., Production of enantiopure styrene oxide by recombinant Escherichia coli synthesizing a two component styrene monooxygenase (2000) Biotechnol Bioeng, 69, pp. 91-100 | ||
| 504 | |a Servi, S., Baker's yeast as a reagent in organic synthesis (1990) Synthesis, pp. 1-24 | ||
| 504 | |a Rotthaus, O., Krüger, D., Demuth, M., Schaffner, K., Reductions of keto- esters with baker's yeast in organic solvents. A comparison with the results in water (1997) Tetrahedron, 53, pp. 935-938 | ||
| 504 | |a Zaks, A., Klibanov, A.M., Enzyme-catalyzed processes in organic solvents (1985) Proc Natl Acad Sci USA, 82, pp. 3192-3196 | ||
| 504 | |a Terradas, F., Teston, H.M., Fitzpatrick, P.A., Klibanov, A.M., Marked dependence of enzyme prochiral selectivity on the solvent (1993) J Am Chem Soc, 115, pp. 390-396 | ||
| 504 | |a Hochuli, E., Taylor, K.E., Dutler, H., Dihydroxiacetone reductase from Mucor javanicus. 2. Identification of the physiological substrate and reactivity towards related compounds (1977) Eur J Biochem, 75, pp. 433-439 | ||
| 504 | |a Peters, J., Sypherd, P.S., Morphology-associated expression of nicotinamide adenine dinucleotide-dependent glutamate dehydrogenase in Mucor racemosus (1979) J Bacteriol, 137, pp. 1134-1139 | ||
| 504 | |a Shimizu, S., Hattori, S., Hata, H., Yamada, H., A novel fungal enzyme, NADPH-depedent carbonyl reductase, showing high specificity to conjugated polyketones. Purification and characterization (1988) Eur J Biochem, 174, pp. 37-44 | ||
| 504 | |a Zazueta-Sandoval, R., Gutiérrez-Corona, J.F., Developmental and environmental influences in the production of a single NAD-dependent fermentative alcohol dehydrogenase by the zygomycete Mucor rouxii (1999) Arch Microbiol, 172, pp. 280-286 | ||
| 504 | |a Haidle, C.W., Storck, R., Control of dimorphism in Mucor rouxii (1966) J Bacteriol, 92, pp. 1236-1244 | ||
| 504 | |a Bartnicki-García, S., Nickerson, W.J., Nutrition, growth, and morphogenesis of Mucor rouxii (1962) J Bacteriol, 83, pp. 841-858 | ||
| 504 | |a Seebach, D., Züger, M., Uber die depolymerisierung von Poly-(R)-3-hydroxy-buttersäureester (PHB) (1982) Helv Chim Acta, 65, pp. 495-504 | ||
| 504 | |a North, M., Baker's yeast reduction of β-ketoesters in petrol (1996) Tetrahedron Letters, 37, pp. 1699-1702 | ||
| 504 | |a Nakamura, K., Inoue, K., Ushio, L., Oka, S., Ohno, A., Stereochemical control on yeast reduction of α-ketoesters. Reduction by immobilized baker's yeast in hexane (1988) J Org Chem, 53, pp. 2589-2593 | ||
| 504 | |a Roser, B., Trehalose, a new approach to premium dried foods (1991) Trends in Food Sci Technol, 2, pp. 166-169 | ||
| 520 | 3 | |a We report the efficient enantioselective reduction of a number of β-ketoesters by mycelial and yeast-like forms of the dimorphic fungus Mucor rouxii in a whole-cell process. Mycelial cells, grown in aerobiosis, were efficient in water, whereas the yeast-like cells, grown in anaerobic medium, were both efficient in water and in organic solvents. Almost 100% of conversion with 97% of enantiomeric excess of the (S) forms of the reduced β-ketoesters was obtained at 15 g biomass (wet weight)/mmol substrate in two hours. The fungal spores, which are the physiologically resistant form of the fungus, also catalyzed the reductive process efficiently and stereoselectively. The freeze-dried as well as the warm-air dried yeast-like cells, rehydrated in a small volume of water, maintained the same efficiency and selectivity of the reaction in organic solvents as the fresh biomass up to at least 4 months. © 2002 Elsevier Science Inc. All rights reserved. |l eng | |
| 536 | |a Detalles de la financiación: Consejo Nacional de Investigaciones Científicas y Técnicas | ||
| 536 | |a Detalles de la financiación: We thank UMYMFOR and LANAIS-EMAR for GC analysis and spectra. We are indebted to CONICET for partial financial support. We are grateful to Miguel Galvagno and Moisés Burachik for helpful discussions. | ||
| 593 | |a Departamento De Química Orgánica, Facultad De Ciencias Exactas Y Naturales, Ciudad Universitaria, 1428, Buenos Aires, Argentina | ||
| 593 | |a Departamento De Química Biológica, Facultad De Ciencias Exactas Y Naturales, Ciudad Universitaria, 1428, Buenos Aires, Argentina | ||
| 690 | 1 | 0 | |a Β-KETOESTERS |
| 690 | 1 | 0 | |a MUCOR ROUXII |
| 690 | 1 | 0 | |a MYCELIAL |
| 690 | 1 | 0 | |a SPORES |
| 690 | 1 | 0 | |a YEAST |
| 690 | 1 | 0 | |a BIOMASS |
| 690 | 1 | 0 | |a CELLS |
| 690 | 1 | 0 | |a ESTERS |
| 690 | 1 | 0 | |a FUNGI |
| 690 | 1 | 0 | |a ORGANIC SOLVENTS |
| 690 | 1 | 0 | |a WATER |
| 690 | 1 | 0 | |a YEAST |
| 690 | 1 | 0 | |a STEREOSELECTIVITY |
| 690 | 1 | 0 | |a REDUCTION |
| 690 | 1 | 0 | |a ESTER DERIVATIVE |
| 690 | 1 | 0 | |a ORGANIC SOLVENT |
| 690 | 1 | 0 | |a WATER |
| 690 | 1 | 0 | |a AEROBIC METABOLISM |
| 690 | 1 | 0 | |a ARTICLE |
| 690 | 1 | 0 | |a BACTERIAL SPORE |
| 690 | 1 | 0 | |a BIOMASS |
| 690 | 1 | 0 | |a CATALYSIS |
| 690 | 1 | 0 | |a CONTROLLED STUDY |
| 690 | 1 | 0 | |a ENANTIOMER |
| 690 | 1 | 0 | |a ENANTIOSELECTIVITY |
| 690 | 1 | 0 | |a FUNGAL CELL |
| 690 | 1 | 0 | |a FUNGUS |
| 690 | 1 | 0 | |a FUNGUS GROWTH |
| 690 | 1 | 0 | |a FUNGUS SPORE |
| 690 | 1 | 0 | |a MORPHOLOGY |
| 690 | 1 | 0 | |a MUCOR |
| 690 | 1 | 0 | |a MUCOR ROUXII |
| 690 | 1 | 0 | |a MYCELIUM |
| 690 | 1 | 0 | |a NONHUMAN |
| 690 | 1 | 0 | |a PHYSIOLOGY |
| 690 | 1 | 0 | |a REDUCTION |
| 690 | 1 | 0 | |a REHYDRATION |
| 690 | 1 | 0 | |a STEREOCHEMISTRY |
| 690 | 1 | 0 | |a YEAST |
| 690 | 1 | 0 | |a AMYLOMYCES ROUXII |
| 690 | 1 | 0 | |a FUNGI |
| 690 | 1 | 0 | |a MUCOR |
| 650 | 1 | 7 | |2 spines |a AEROBIOSIS |
| 700 | 1 | |a N.Pereyra, E. | |
| 700 | 1 | |a Argimón, S. | |
| 700 | 1 | |a Moreno, S. | |
| 700 | 1 | |a Baldessari, A. | |
| 773 | 0 | |d 2002 |g v. 30 |h pp. 596-601 |k n. 5 |p Enzyme Microb. Technol. |x 01410229 |w (AR-BaUEN)CENRE-1003 |t Enzyme and Microbial Technology | |
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