Abstract:
Whole cells of the yeast Rhodotorula minuta were used in the biotransformation of dialkyl esters of 2-oxoglutaric acid. Almost 100% of conversion with 97-98% of enantiomeric excess of the (S) form of 2-hydroxydiesters was obtained through an enantioselective reduction of dimethyl and diethyl 2-oxoglutarate. When longer alkoxy chain 2-oxoglutarates were used as substrates, the corresponding 4-hydroxybutyric esters were obtained, suggesting a combination process including hydrolysis, decarboxylation and reduction. The cells showed a remarkable high productivity: high conversion and enantiomeric excess were obtained at 2 g wet weight mmol-1 substrate.
Registro:
Documento: |
Artículo
|
Título: | An efficient biotransformation of dialkyl esters of 2-oxoglutaric acid by Rhodotorula minuta whole cells |
Autor: | Rustoy, E.; Cerrutti, P.; Galvagno, M.; Baldessari, A. |
Filiación: | Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Buenos Aires, Argentina Departamento de Ingeniería Química, Facultad de Ingeniería, Universidad de Buenos Aires, Buenos Aires, Argentina IIB-Intech-CONICET-UNSAM, Buenos Aires, San Martín, Argentina
|
Palabras clave: | Biotransformation; Dialkyl 2-oxoglutaric acid esters; Rhodotorula minuta; Cells; Enantiomers; Enantioselectivity; Yeast; Biotransformation; Dialkyl esters; Oxoglutaric acid; Esters; 2 oxoglutaric acid; 4 hydroxybutyric acid; article; biocatalyst; biotransformation; decarboxylation; enantiomer; enantioselectivity; hydrolysis; nonhuman; reduction; Rhodotorula; Rhodotorula minuta; Rhodotorula minuta |
Año: | 2008
|
Volumen: | 26
|
Número: | 3
|
Página de inicio: | 204
|
Página de fin: | 209
|
DOI: |
http://dx.doi.org/10.1080/10242420701661172 |
Título revista: | Biocatalysis and Biotransformation
|
Título revista abreviado: | Biocatal. Biotransform.
|
ISSN: | 10242422
|
CODEN: | BOBOE
|
CAS: | 2 oxoglutaric acid, 328-50-7; 4 hydroxybutyric acid, 591-81-1
|
Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_10242422_v26_n3_p204_Rustoy |
Referencias:
- Baiker, A., Reflections on chiral metal surfaces and their potential for catalysis (2005) Catal Today, 100, pp. 159-170
- Baskar, B., Ganesh Pandian, N., Priya, K., Chadha, A., Asymmetric reduction of alkyl 2-oxo-4-arylbutanoates and -but-3-enoates by Candida parapsilosis ATCC 7330: assignment of the absolute configuration of ethyl 2-hydroxy-4-(p-methylphenyl)but-3-enoate by 1H NMR (2004) Tetrahedron: Asymmetry, 15, pp. 3961-3966
- Boutoute, P., Mousset, G., Veschambre, H., Regloselective or enantiogenic electrochemical and microbial reductions of 1,2-diketones (1998) New J Chem, 22, pp. 247-251
- 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
- Coppola, G.M., Schuster, H.F., (2000) Chiral α-hydroxyacids in Enantioselective Synthesis, , Wiley-VCH, Weinheim
- Crocq, V., Masson, C., Winter, J., Richard, C., Lemaitre, G., Lenay, J., Vivat, M., Prat, D., Synthesis of trimegestone: The first industrial application of baker's yeast mediated reduction of a ketone (1997) Org Proc Res Dev, 1, pp. 2-13
- Dao, D.H., Kawai, Y., Hida, K., Hornes, S., Nakamura, K., Ohno, A., Stereochemical control in microbial reduction. 30: Reduction of alkyl 2-oxo-4-phenylbutyrate as precursors of angiotensin converting enzyme (ACE) inhibitors (1998) Bull Chem Soc Jpn, 71, pp. 425-432
- Dao, D.H., Okamura, M., Akasaka, T., Kawai, Y., Hida, K., Ohno, A., Stereochemical control in microbial reduction. Part 31: Reduction of alkyl 2-oxo-4-arylbutanoates by baker's yeast under selected reaction conditions (1998) Tetrahedron: Asymmetry, 9, pp. 2725-2737
- Drioli, S., Nitti, P., Pitacco, G., Tossut, L., Valentin, E., Enantiomerically pure tetrahydro-5-oxo-2-furancarboxylic esteres from dialkyl 2-oxo-glutarates (1999) Tetrahedron: Asymmetry, 10, pp. 2713-2728
- Fernandes, P., Cruz, A., Angelova, B., Pinheiro, H.M., Cabral, J.S.M., Microbial conversion of steroids compounds: Recent developments (2003) Enzyme Microb Technol, 32, pp. 688-705
- García-Urdiales, E., Alfonso, I., Gotor, V., Enantioselective enzymatic desymmetrizations in organic synthesis (2005) Chem Rev, 105, pp. 313-354
- Ishihara, K., Yamguchi, H., Hamada, H., Nakajiman, N., Nakamura, K., Stereocontrolled reduction of α-keto esters with thermophilic actinomyecete Streptomyces thermocyaneviolaceus IFO 14271 (2000) J Mol Catal B: Enzym, 10, pp. 429-434
- Kaluzna, I.A., Matsuda, T., Sewell, A.K., Stewart, J.D., Systematic investigation of Saccharomyces cerevisiae enzymes catalyzing carbonyl reductions (2004) J Am Chem Soc, 126, pp. 12827-12832
- Kayser, M.M., Mihovilovic, M.D., Kearns, J., Feicht, H., Stewart, J.D., Baker's yeast-mediated reductions of (α-Keto Esters and an (β-Keto-(-Lactam. Two routes to the paclitaxel side chain (1999) J Org Chem, 64, pp. 6603-6610
- Kirk, P., Cannon, P., David, J., Stalpers, J., (2001) Ainsworth & Bisby's Dictionary of the Fungi, , CAB International, Wellingford
- Mangone, C.P., Pereyra, E.N., Argimon, S., Moreno, S., Baldessari, A., Chemo- and stereoreduction of β-ketoesters by spores and various morphological forms of Mucor rouxii (2002) Enzyme Microb Technol, 30, pp. 596-601
- Martin, D.A.G., Reynolds, W.F., Reese, P.B., Stemodane skeletal rearrangement: Chemistry and microbial transformation (2005) Phytochemistry, 66, pp. 901-909
- Nakamura, K., Kondo, S., Nakajima, N., Ohno, A., Mechanistic study for stereochemical control of microbial reduction of α-ketoesters in an organic solvent (1995) Tetrahedron, 51, pp. 687-694
- Nakamura, K., Yamanaka, R., Matsuda, T., Harada, T., Recent developments in asymmetric reduction of ketones with biocatalysts (2003) Tetrahedron: Asymmetry, 14, pp. 2659-2681
- North, M., Synthesis and application of non-racemic cyanohydrins (2003) Tetrahedron: Asymmetry, 14, pp. 147-176
- Patel, R.N., Chu, L., Chidambaram, R., Zhu, J., Khant, J., Enantioselective microbiol reduction of 2-oxo-2-(1′, 2′, 3′, 4′-tetrahydro-1′, 1′, 4′, 4′-tetramethyl-6′-naphthalenyll acetic acid and its ethyl ester (2002) Tetrahedron: Asymmetry, 13, pp. 349-355
- Radosevich, A.T., Musich, C., Toste, F.D., Vanadium catalyzed asymmetric oxidation of α-hydroxy esters using molecular oxygen as stoichiometric oxidant (2005) J Am Chem Soc, 127, pp. 1090-1091
- Ramachandran, P.V., Pitre, S., Brown, H.C., Selective reductions. α-, β-, and γ-keto acids using diisopinocamphenylborane and intermolecular asymmetric reductions of the corresponding esters with β-chlorodiisocamphenylborane (2002) J Org Chem, 67, pp. 5315-5319
- Rathbone, D.A., Bruce, N.C., Microbial transformation of alkaloids (2002) Curr Opin Microbiol, 5, pp. 274-281
- Rustoy, E.M., Pereyra, E.N., Moreno, S., Baldessari, A., Combination strategy using pure enzymes and whole cells as biocatalysts for the preparation of 2-hydroxyesters and lactones from 2-oxoglutaric acid (2004) Tetrahedron: Asymmetry, 15, pp. 3763-3768
- 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 β-blocker (R)-nifenalol. Tetrahedron: Asymmetry, 17, pp. 1769-1774 (2006) Tetrahedron: Asymmetry, 17, pp. 1769-1774
- Zhu, D., Mukherjee, C., Rozzell, J.D., Kambourakis, S., Hua, L., A recombinant ketoreductase tool-box. Assessing the substrate selectivity and stereoselectivity towards the reduction of β-ketoesters (2006) Tetrahedron, 62, pp. 901-905
- Zymanczyk-Duda, E., Klimek-Ochab, M., Kafarski, P., Lejczak, B., Stereochemical control of biocatalytic asymmetric reduction of diethyl 2-oxopropylphosphonate employing yeasts (2005) J Organomet Chem, 690, pp. 2593-2596
Citas:
---------- APA ----------
Rustoy, E., Cerrutti, P., Galvagno, M. & Baldessari, A.
(2008)
. An efficient biotransformation of dialkyl esters of 2-oxoglutaric acid by Rhodotorula minuta whole cells. Biocatalysis and Biotransformation, 26(3), 204-209.
http://dx.doi.org/10.1080/10242420701661172---------- CHICAGO ----------
Rustoy, E., Cerrutti, P., Galvagno, M., Baldessari, A.
"An efficient biotransformation of dialkyl esters of 2-oxoglutaric acid by Rhodotorula minuta whole cells"
. Biocatalysis and Biotransformation 26, no. 3
(2008) : 204-209.
http://dx.doi.org/10.1080/10242420701661172---------- MLA ----------
Rustoy, E., Cerrutti, P., Galvagno, M., Baldessari, A.
"An efficient biotransformation of dialkyl esters of 2-oxoglutaric acid by Rhodotorula minuta whole cells"
. Biocatalysis and Biotransformation, vol. 26, no. 3, 2008, pp. 204-209.
http://dx.doi.org/10.1080/10242420701661172---------- VANCOUVER ----------
Rustoy, E., Cerrutti, P., Galvagno, M., Baldessari, A. An efficient biotransformation of dialkyl esters of 2-oxoglutaric acid by Rhodotorula minuta whole cells. Biocatal. Biotransform. 2008;26(3):204-209.
http://dx.doi.org/10.1080/10242420701661172