Rhodotorula minuta-mediated bioreduction of 1,2-diketones

The reduction of cyclic and acyclic 1,2-diketones was investigated by employing whole cells of the yeast Rhodotorula minuta as biocatalyst. The reactions showed a variable degree of regio- and enantioselectivity depending on the nature of the substrate. In the case of cyclic diketones, the reduction...

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Autor principal: Monsalve, L.N
Otros Autores: Cerrutti, P., Galvagno, M.A, Baldessari, A.
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: 2010
Acceso en línea:Registro en Scopus
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024 7 |2 cas  |a 2,3 butanedione, 431-03-8 
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100 1 |a Monsalve, L.N. 
245 1 0 |a Rhodotorula minuta-mediated bioreduction of 1,2-diketones 
260 |c 2010 
270 1 0 |m Baldessari, A.; Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, C1428EGA Buenos Aires, Argentina; email: alib@qo.fcen.uba.ar 
506 |2 openaire  |e Política editorial 
504 |a Anisimov, V.N., Premature ageing prevention: Limitations and perspectives of pharmacological interventions (2006) Curr Drug Targets, 7, pp. 1485-1503 
504 |a Besse, P., Bolte, J., Fauve, A., Veschambre, H., Baker's yeast reduction of α-diketones: Investigation and control of the enzymatic pathway (1993) Bioorg Chem, 21, pp. 342-353 
504 |a Biradar, A.V., Sathe, B.R., Umbarkar, S.B., Dongare, M.K., Selective cis-dihydroxylation of olefins using recyclable homogeneous molybdenum acetylide catalyst (2008) J Mol Catal A: Chem, 285, pp. 111-119 
504 |a Bode, S.E., Wolberg, M., Muller, M., Stereoselective synthesis of 1,3-diols (2006) Synthesis, pp. 557-588 
504 |a Boutoute, P., Mousset, G., Veschambre, H., Regioselective or enantiogenic electrochemical and microbial reductions of 1,2-diketones (1998) New J Chem, pp. 247-251 
504 |a Cinelli, G., Cuomo, F., Hochkoeppler, A., Ceglie, A., Lopez, F., Use of Rhodotorula minuta live cells hosted in water-in-oil macroemulsion for biotransformation reaction (2006) Biotechnol Prog, 22, pp. 689-695 
504 |a Clerici, A., Porta, O., Reduction of aromatic carbonyl compounds promoted by titanium trichloride in basic media (1985) J Org Chem, 50, pp. 76-81. , Stereochemistry studies 
504 |a Demir, A.S., Hamamci, H., Ayhan, P., Duygu, A.N., Igdir, A.C., Capanoglu, D., Fungi mediated conversion of benzil to benzoin and hydrobenzoin (2004) Tetrahedron Asymm, 15, pp. 2579-2582 
504 |a Demir, A.S., Ayhan, P., Demirtas, U., Erkilic, U., Fusarium roseum and Aspergillus oryzae-mediated enantioselective reduction of benzyls to benzoins (2008) J Mol Catal B: Enzym, 55, pp. 164-168 
504 |a Edegger, K., Stampfer, W., Seisser, B., Faber, K., Mayer, S.F., Oehrlein, R., Hafner, A., Kroutil, W., Regio-and stereoselective reduction of diketones and oxidation of diols by biocatalytic hydrogen transfer (2006) Eur J Org Chem, pp. 1904-1909 
504 |a Fang, Q.K., Han, Z., Grover, P., Kessler, D., Senanayade, C.H., Wald, S.A., Rapid access to enantiopure bupropion and its major metabolite by stereospecific nucleophilic substitution on an α-ketotriflate (2000) Tetrahedron Asymm, 11, pp. 3659-3663 
504 |a Fries, R.W., Bohlken, D.P., Plapp, B.V., 3-Substituted pyrazole derivatives as inhibitors and inactivators of alcohol dehydrogenase (1979) J Med Chem, 22, pp. 356-359 
504 |a Garcia-Urdiales, E., Alfonso, I., Gotor, V., Enantioselective enzymatic desymmetrizations in organic synthesis (2005) Chem Rev, 105, pp. 313-354 
504 |a Hashimoto, T., Maruoka, K., Recent development and application of chiral phase-transfer catalysts (2007) Chem Rev, 107, pp. 5656-5682 
504 |a Hayakawa, R., Sahara, T., Shimizu, M., Reduction of 1,2-diketones with titanium tetraiodide: A simple approach to α-hydroxy ketones (2000) Tetrahedron Lett, 41, pp. 7939-7942 
504 |a Hoyos, P., Sansottera, G., Fernandez, M., Molinari, F., Sinisterra, J.V., Alcantara, A.R., Enantioselective monoreduction of different 1,2-diaryl-1,2-diketones catalysed by lyophilised whole cells from Pichia glucozyma (2008) Tetrahedron, 64, pp. 7929-7936 
504 |a Hummel, W., Boermann, F., Kula, M.R., Purification and characterization of an acetoin dehydrogenase from Lactobacillus kefir suitable for the production of (+)-acetoin (1989) Biocatal Biotransform, 2, pp. 293-308 
504 |a Ikariya, T., Blacker, J., Asymmetric transfer hydrogenation of ketones with bifunctional transition metal-based molecular catalysts (2007) Acc Chem Res, 40, pp. 1300-1308 
504 |a Kosjek, B., Satmpfer, W., Pogorevc, W., Goessler, W., Faber, K., Kroutil, W., Purification and characterization of a chemotolerant alcohol dehydrogenase applicable to coupled redox reactions (2004) Biotechnol Bioeng, 86, pp. 55-62 
504 |a Kume, Y., Ohta, H., Enzyme-mediated enantiofacedifferentiating hydrolysis of α-substituted sulfur-containing cyclic ketone enol esters (1992) Tetrahedron Lett, 33, pp. 6367-6370 
504 |a Mohr, J.T., Krout, M.R., Stoltz, B.M., Natural products as inspiration for the development of asymmetric catalysis (2008) Nature, 455, pp. 323-332 
504 |a Moore, J.C., Pollard, D.K., Kosjek, B., Devine, P.N., Advances in enzymatic reduction of ketones (2007) Acc Chem Res, 40, pp. 1412-1419 
504 |a Nakamura, K., Kondo, S., Kawai, Y., Hida, K., Kitano, K., Ohno, A., Enantio-and regioselective reduction of α-diketones by baker's yeast (1996) Tetrahedron Asymm, 7, pp. 409-412 
504 |a Nakamura, K., Yamanaka, R., Matsuda, T., Harada, T., Recent developments in asymmetric reduction of ketones with biocatalysts (2003) Tetrahedron Asymm, 14, pp. 2659-2681 
504 |a Neisius, N.M., Plietker, B., Diastereoselective Ru-catalyzed cross-metathesis-dihydroxylation sequence. An efficient approach toward enantiomerically enriched syn-diols (2008) J Org Chem, 73, pp. 3218-3227 
504 |a Ramaswamy, S., Kratzer, D.A., Hershey, A.D., Rogers, P.H., Arnone, A., Eklund, H., Plapp, B.V., Crystallization and preliminary crystallographic studies of Saccharomyces cerevisiae alcohol dehydrogenase i (1994) J Mol Biol, 235, pp. 777-779 
504 |a Rustoy, E., Cerrutti, P., Galvagno, M., Baldessari, A., An efficient biotransformation of dialkyl esters of 2-oxoglutaric acid by Rhodotorula minuta whole cells (2008) Biocatal Biotransform, 26, pp. 204-209 
504 |a Segretario, J.P., Slezynski, N., Zuman, P., Polarographic reduction of aldehydes and ketones: Part XXVIII. 1,2-cyclohexanedione (1986) J Electronanal Chem, 214, pp. 259-273 
504 |a Seki, M., A practical synthesis of a key chiral drug intermediate via asymmetric organocatalysis (2008) Synlett, pp. 164-176 
504 |a Stampfer, W., Kosjek, B., Faber, K., Kroutil, W., Biocatalytic asymmetric hydrogen transfer employing Rhodococcus ruber DSM 44541 (2003) J Org Chem, 68, pp. 402-406 
504 |a Trivić, S., Leskovac, V., Structure and function of yeast alcohol dehydrogenase (2000) J Serb Chem Soc, 65, pp. 207-227 
504 |a Wallace, O.B., Smith, D.W., Deshpande, M.S., Polson, C., Felsenstein, K.M., Inhibitors of Aβ production: Solid phase synthesis and SAR of α-hydroxycarbonyl derivatives (2003) Bioorg Med Chem Lett, 13, pp. 1203-1206 
504 |a Yang, W., Xu, J.H., Xie, Y., Xu, Y., Zhao, G., Lin, G.Q., Asymmetric reduction of ketones by employing Rhodotorula sp AS2-2241 and synthesis of the α-blocker (R)-nifelalol (2006) Tetrahedron Asymm, 17, pp. 1769-1774 
504 |a Zhang, W., Shi, M., Reduction of activated carbonyl groups by alkyl phosphines: Formation of α-hydroxyesters and ketones (2006) Chem Commun, pp. 1218-1220 
520 3 |a The reduction of cyclic and acyclic 1,2-diketones was investigated by employing whole cells of the yeast Rhodotorula minuta as biocatalyst. The reactions showed a variable degree of regio- and enantioselectivity depending on the nature of the substrate. In the case of cyclic diketones, the reduction afforded a mixture of diastereomeric diols only. The reduction of acyclic diketones allowed production of both the hydroxy ketone and the diol, in a two-step reaction. The first step was highly regio- and stereoselective, affording the hydroxy ketone of (S)-configuration with high enantiomeric excess. After longer reaction times the corresponding (S,S)-diols were obtained in high yield and diastereomeric excess. © 2010 Informa UK Ltd.  |l eng 
536 |a Detalles de la financiación: Agencia Nacional de Promoción Científica y Tecnológica, PICT 2005 06-32735 
536 |a Detalles de la financiación: We thank UBA (X089 (2004-2007) and X010 (2008-2010), ANPCyT (PICT 2005 06-32735) for partial financial support. A.B. and M.A.G. are Research Members of CONICET. The authors 
593 |a Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, C1428EGA Buenos Aires, Argentina 
593 |a Departamento de Ingeniería Química, Facultad de Ingeniería, Universidad de Buenos Aires, Buenos Aires, Argentina 
593 |a IIB-Intech-CONICET-UNSAM, Buenos Aires, Argentina 
690 1 0 |a 1,2-DIKETONES 
690 1 0 |a BIOREDUCTION 
690 1 0 |a RHODOTORULA MINUTA 
690 1 0 |a BIOREDUCTIONS 
690 1 0 |a DIASTEREOMERIC 
690 1 0 |a DIASTEREOMERIC EXCESS 
690 1 0 |a DIKETONES 
690 1 0 |a ENANTIOMERIC EXCESS 
690 1 0 |a HIGH YIELD 
690 1 0 |a REACTION TIME 
690 1 0 |a STEREO-SELECTIVE 
690 1 0 |a TWO-STEP REACTIONS 
690 1 0 |a WHOLE CELL 
690 1 0 |a ENANTIOSELECTIVITY 
690 1 0 |a KETONES 
690 1 0 |a 1,2 CYCLOHEXANEDIOL DERIVATIVE 
690 1 0 |a 1,2 DIKETONE DERIVATIVE 
690 1 0 |a 2 PHENYL 2,3 PROPANEDIONE 
690 1 0 |a 2,3 BUTANEDIONE 
690 1 0 |a 2,3 PENTANEDIONE 
690 1 0 |a DIKETONE 
690 1 0 |a UNCLASSIFIED DRUG 
690 1 0 |a ARTICLE 
690 1 0 |a CONTROLLED STUDY 
690 1 0 |a ENANTIOMER 
690 1 0 |a ENANTIOSELECTIVITY 
690 1 0 |a GAS LIQUID CHROMATOGRAPHY 
690 1 0 |a NONHUMAN 
690 1 0 |a REDUCTION 
690 1 0 |a RHODOTORULA 
690 1 0 |a RHODOTORULA MINUTA 
690 1 0 |a STEREOCHEMISTRY 
690 1 0 |a RHODOTORULA MINUTA 
700 1 |a Cerrutti, P. 
700 1 |a Galvagno, M.A. 
700 1 |a Baldessari, A. 
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