Asymmetric reduction of ethyl 4-chloro-3-oxobutanoate in an aqueous/organic solvent biphasic system with microorganism

Gao Xiao Hua Xue Gong Cheng Xue Bao/Journal of Chemical Engineering of Chinese Universities

Volumn 21, Issue 2, 2007, Pages 310-315

  He, Jun Yao ^a   Sun, Zhi Hao ^a   Zheng, Pu ^a   Han, Li ^a  

^a JIANGNAN UNIVERSITY   (China)

Author keywords

Asymmetric reduction; Aureobasidium pullulans SW0202; Ethyl (S) 4 chloro 3 hydroxybutanoate; Ethyl 4 chloro 3 oxobutanoate

Indexed keywords

BIOCOMPATIBILITY; BIOCONVERSION; CATALYSTS; MICROORGANISMS; ORGANIC SOLVENTS; PH; REACTION RATES; REDUCTION; WATER;

ASYMMETRIC REDUCTION; AUREOBASIDIUM PULLULANS SW0202; ETHYL (S)-4-CHLORO-3-HYDROXYBUTANOATE; ETHYL 4-CHLORO-3-OXOBUTANOATE;

ESTERS;

EID: 34249724556     PISSN: 10039015     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (27)

1. Zhou B, Gopalan A S, VanMiddlesworth F et al. Stereochemical control of yeast reductions. 1. Asymmetric synthesis of L-carnitine [J]. J Am Chem Soc, 1983, 105(18): 5925-5926.
2. Karanewsky D S, Badia M C, Ciosek C P J et al. Phosphorus-containing inhibitors of HMG-CoA reductase. 1, 4-[2-(arylethyl)hydroxyphosphinyl]-3-hydroxy-butanoic acids: a new class of cell-selective inhibitors of cholesterol biosynthesis [J]. J Med Chem, 1990, 33(11): 2952-2956.
3. Patel R N, McMamee C G, Banerjee A et al. Stereoselective reduction of p-keto esters by Geotrichum candidum [J]. Enzyme Microb Technol, 1992, 14(9): 731-738.
4. LIU Hui, LIN Jian-ping, WU Jian-ping et al. Study on the kinetics of biosynthesis of S-adenosyl-L-methionine by the yeast cells [J]. J Chem Eng of Chinese Univ, 2004, 18(6): 168-173.
5. OU Zhi-min, JIN Zhi-hua, WU Jian-ping et al. Kinetic model of asymmetric reduction of 2'-chloroacetophenone by Saccharomyces cerevisiae B5 with coenzyme regeneration process [J]. J Chem Eng of Chinese Univ, 2005, 19(4): 511-517.
6. Hunt J R, Carter A S, Murrell J C et al. Yeast catalysed reduction of p-keto esters (1): Factors affecting whole-cell catalytic activity and stereoselectivity [J]. Biocatal Biotransform, 1995, 12: 159-178.
7. Yasohara Y, Kizaki N, Hasegawa J et al. Synthesis of optically active ethyl 4-chloro-3-hydroxybutanoate by microbial reduction [J]. Appl Microbiol Biotechnol, 1999, 51: 847-851.
8. Saratani Y, Uheda E, Yamamoto H et al. Steroselective reduction of ethyl 4-chloro-3-oxobutanoate by fungi [J]. Biosci Biotechnol Biochem, 2001, 65(7): 1676-1679.
9. YANG Zhong-hua, YAO Shan-jing. Asymmetric reduction of ethyl 4-chloro-3-oxobutanoate to ethyl 4-chloro-3-hydroxybutanoate by yeast cells in aqueous phase [J]. Chinese J Catal, 2004, 25(6): 434-438.
10. Shieh W R, Gopalan A S, Sih C J. Stereochemical control of yeast reductions 5. Characterization of the oxidoreductases involved in the reduction of P-keto esters [J]. J Am Chem Soc, 1985, 107(10): 2993-2994.
11. Yamada H, Shimizu S, Kataoka M et al. A novel NADP-dependent aldehyde reductase catalyzing asymmetric reduction of P-keto esters, from Sporobolomyces salmonicolor: purification and characterization [J]. FEMS Microbiol Lett, 1990, 70(1): 45-48.
12. Kataoka M, Skai H, Morikawa T et al. Characterization of aldehyde reductase of Sporobolomyces salmonicolor [J]. Biochim Biophys Acta, 1992, 1122(1): 57-62.
13. Kita K, Nakase K, Yanase H et al. Purification and characterization of new aldehyde reductases from Sporobolomyces salmonicolor AKU-4429 [J]. J Mol Catalysis B: Enzymatic, 1999, 6: 305-313.
14. Wada M, Kataoka M, Kawabata H et al. Purification and characterization of NADP-dependent carbonyl reductase, involved in stereoselective reduction of ethyl 4-chloro-3-oxobutanoate, from Candida magnoliae [J]. Biosci Biotechnol Biochem, 1998, 62(2): 280-285.
15. Wada M, Kawabata H, Yoshizumi A et al. Occurrence of multiple ethyl 4-chloro-3-oxobutanoate-reducing enzymes in Candida magnoliae [J]. J Biosci Bioeng, 1999, 87(2): 144-148.
16. Wada M, Kawabata H, Kataoka M et al. Purification and characterization of an aldehyde reductase from Candida magnoliae [J]. J Mol Catal B: Enzymatic, 1999, 6: 333-339.
17. Kataoka M, Doi Y, Sim T S et al. A novel NADP-dependent carbonyl reductase of Candida macedoniensis: purification and characterization [J]. Arch Biochem Biophys, 1992, 294(2): 469-474.
18. Peters J, Miuth T, Kula M R. A novel NADP-dependent carbonyl reductase with an extremely broad substrate range from Candida parapsilosis: purification and characterization [J]. Enzyme Microb Technol, 1993, 15(11): 950-958.
19. Yamamoto H, Matsuyama A, Kobyashi Y. Synthesis of ethyl (5)-4-chloro-3-hydroxybutanoate using fabG-homologues [J]. Appl Microbiol Biotechnol, 2003, 61(2): 133-139.
20. Kataoka M, Rohani L P S, Yamamoto K et al. Enzymatic production of ethyl (R)-4-chloro-3-hydroxybutanoate: asymmetric reduction of ethyl 4-chloro-3-oxobutanoate by an Escherichia coli tranformant expressing the aldehyde reductase gene from yeast [J]. Appl Microbiol Biotechnol, 1997, 48(6): 699-703.
21. Kizaki N, Yasohara Y, Hasegawa J et al. Synthesis of optically pure ethyl (S)-4-chloro-3-hydroxybutanoate by Escherichia coli tranformant cells coexpressing the carbonyl reductase and glucose dehydrogenase genes [J]. Appl Microbiol Biotechnol, 2001, 55: 590-595.
22. SUN Zhi-hao, ZHENG Pu, HE Jun-yao et al. A strain and method for the biocatalytic synthesis of ethyl (S)-4-chloro-3-hydroxybutanoate [P]. Chinese Patent: CN 1778889A, 2006-05-31.
23. Shimizu S, Kataoka M, Katoh M et al. Stereoselective redction of ethyl 4-chloro-3-oxobutanoate by a microbial aldehyde reductase in an organic solvent-water diphasic system [J]. Appl Environ Microbiol, 1990, 56(8): 2374-2377.
24. Dahl A C, Madsen J Φ. Baker's yeast: production of D-and L-3-hydroxy esters [J]. Tetrahedron: Asymmetry, 1998, 9: 4395-4417.
25. León R, Fernandes P, Pinheiro H M et al. Whole-cell biocatalysis in organic media [J]. Enzyme Microb Technol, 1998, 23(7-8): 483-500.
26. Laane C, Boeren S, Vos K et al. Rules for the optimization of biocatalysis in organic solvents [J]. Biotechol Bioeng, 1987, 30(1): 81-87.
27. He J Y, Sun Z H, Ruan W Q et al. Biocatalytic synthesis of ethyl (S)-4-chloro-3-hydroxybutanoate in an aqueous-organic solvent biphasic system using Auriobasidimpullulans CGMCC1244 [J]. Process Biochem, 2006, 41(1): 244-249.