Stereoselective bioreduction of 1-(5-phenylfuran-2-yl)-ethanones mediated by baker's yeast

Biocatalysis and Biotransformation

Volumn 30, Issue 2, 2012, Pages 177-183

  Trif, Maria ^a   Kall, Noémi Hajnalka ^a   Naghi, Mara Ana ^a   Bencze, Lászl Csaba ^a  

^a BABE BOLYAI UNIVERSITY   (Romania)

Author keywords

Baker's yeast; Bioreduction; Cellular biotransformation; Phenylfuran 2 yl ethanols; Stereoselective

Indexed keywords

BAKER'S YEAST; BIOREDUCTIONS; CELLULAR BIOTRANSFORMATION; PHENYLFURAN-2-YL-ETHANOLS; STEREO-SELECTIVE;

BIOCHEMISTRY; BIOCONVERSION; BIOTECHNOLOGY;

STEREOSELECTIVITY;

ALCOHOL DERIVATIVE; FURAN DERIVATIVE; PHENYL GROUP;

ARTICLE; BIOTRANSFORMATION; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; ENANTIOMER; FERMENTATION; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; SACCHAROMYCES CEREVISIAE; STEREOCHEMISTRY; STEREOSELECTIVE BIOREDUCTION; SYNTHESIS;

EID: 84858816048     PISSN: 10242422     EISSN: 10292446     Source Type: Journal    
DOI: 10.3109/10242422.2011.638374     Document Type: Article

References (25)

1. Bencze LC, Paizs C, Toşa MI, Irimie FD. 2010. Substituent effects on the stereochemical outcome of the baker's yeast-mediated biotransformation of α-hydroxy-and α-acetoxyme-thyl-5-phenylfuran-2-yl-ethanones. Tetrahedron: Asymmetry; 21: 356-364.
2. Bencze LC, Paizs C, Toşa MI, Irimie FD. 2011. Sequential use of regio-and stereoselective lipases for the efficient kinetic resolution of racemic 1-(5-phenylfuran-2-yl)ethane-1,2-diols. Tetrahedron: Asymmetry; 22: 675-683.
3. Busto E, Gotor-Fernandez V, Gotor V. 2006. Biocatalytic preparation of optically active 4-(N, N-dimethylamino)pyridines for application in chemical asymmetric catalysis. Tetrahedron: Asymmetry; 17: 1007-1016.
4. Cui JN, Ema T, Sakai T, Utaka M. 1998. Control of enantiose-lectivity in the baker's yeast asymmetric reduction of y-chloro (5-diketones to y-chloro (S)-3-hydroxy ketones. Tetrahedron: Asymmetry; 9: 2681-2692. (Pubitemid 28394395)
5. Dao DH, Okamura M, Akasaka T, Kawai Y, Hida K, Ohno A. 1998a. Stereochemical control in microbial reduction. Part 31: Reduction of alkyl 2-oxo-4-arylbutyrates by baker's yeast under selected reaction conditions. Tetrahedron: Asymmetry; 9: 2725-2737. (Pubitemid 28394399)
6. Dao DH, Kawai Y, Hida K, Hornes S, Nakamura K, Ohno A, et al. 1998b. Stereochemical control in microbial reduction. 30. Reduction of alkyl 2-oxo-4-phenylbutyrate as precursors of angiotensin converting enzyme (ACE) inhibitors. Bull Chem Soc Jpn; 71: 425-432.
7. Farina V, Reeves JT, Senanayake CH, Song JJ. 2006. Asymmetric synthesis of active pharmaceutical ingredients. Chem Rev; 106: 2734-2793. (Pubitemid 44207755)
8. Forni A, Moretti I, Prati F, Torre G. 1994. Stereochemical control in yeast reduction of fluorinated 3-diketones. Tetrahedron; 50: 11995-12000. (Pubitemid 24306820)
9. Huang QQ, Huang M, Nan FJ, Ye QZ. 2005. Metalloform-selective inhibition: synthesis and structure-activity analysis of Mn(II)-form-selective inhibitors of Escherichia coli methionine ami-nopeptidase. Bioorg Med Chem Lett; 15: 5386-5391. (Pubitemid 41562955)
10. Kaluzna I, Andrew AA, Bonilla M, Martzen MR, Stewart JD. 2002. Enantioselective reductions of ethyl 2-oxo-4-phenylbu-tyrate by Saccharomyces cerevisiae dehydrogenases. J Mol Catal B: Enzym; 17: 101-105. (Pubitemid 34275482)
11. Matsuda T, Yamanaka R, Nakamura K. 2009. Recent progress in biocatalysis for asymmetric oxidation and reduction. Tetrahedron: Asymmetry; 20: 513-557.
12. Meerwein H, Buchner E, Emster K. 1939.über die einwirkung aromatischer diazoverbindungen auf a,|5-unges ä ttigte carbon- ylverbindungen. J Prakt Chem; 152: 237-266.
13. Meth-Cohn O, Horak RM, Fouche G. 1994. Baker's yeast-mediated transformations of a-keto epoxides. J Chem Soc Perkin Trans; 1: 1517-1527.
14. Nakamura K, Kawai Y, Nakajima N, Ohno A. 1991. Stereochemical control of microbial reduction. 17. A method for controlling the enantioselectivity of reductions with bakers'yeast. J Org Chem; 56: 4778-4783.
15. Nakamura K, Higaki M, Ushio K, Oka S, Ohno A, 1995. Stereochemical control of microbial reduction. 2. Reduction of (5-keto esters by immobilized bakers'yeast. Tetrahedron Lett; 26: 4213-4216.
16. Nishio K, Fukuhara A, Omata Y, Saito Y, Yamaguchi S, Kato H, et al. 2008. Characterization of novel furan compounds on the basis of their radical scavenging activity and cytoprotective effects against glutamate-and lipopolysaccharide-induced insults. Bioorg Med Chem; 16: 10332-10337. (Pubitemid 50315313)
17. Paizs C, Toşa MI, Majdik C, Moldovan PV, Novák L, Kolonits P, et al. 2003. Optically active 1-(benzofuran-2-yl)ethanols and ethane-1,2-diols by enantiotopic selective bioreductions. Tetrahedron: Asymmetry; 14: 1495-1501. (Pubitemid 36588848)
18. Prelog V. 1964. Specification of the stereospecificity of some oxido-reductases by diamond lattice sections. Pure Appl Chem; 9: 119-130.
19. Shi YG, Fang Y, Ren YP, Guan HL, Zhang JY. 2009. Applying alpha-phenacyl chloride to the enantioselective reduction of ethyl 2-oxo-4-phenylbutyrate with baker's yeast. J Chem Technol Biotechnol; 84: 681-688.
20. Takeshita M, Terada K, Akutsu N, Yoshida S, Sato T. 1987. Synthesis of optically active hetero alkylaryl alcohols by baker's yeast. Heterocycles; 26: 3051-3054.
21. Toşa MI, Paizs C, Majdik C, Novák L, Kolonits P, Irimie FD, Poppe L. 2002a. Synthesis of optically active 3-substituted-10-alkyl-10H- phenothiazine-5-oxides by enantioselective biotrans-formations. Tetrahedron: Asymmetry; 13: 211-221. (Pubitemid 34258488)
22. Toşa MI, Paizs C, Majdik C, Moldovan PV, Novák L, Kolonits P, et al. 2002b. Baker's yeast mediated preparation of (10-alkyl-10H- phenothiazin-3-yl)methanols. J Mol Catal B: Enzym; 17: 241-248. (Pubitemid 34663845)
23. Toşa MI, Podea PV, Paizs C, Irimie FD. 2008. Chemoenzymatic synthesis of (R)-and (S)-1-heteroarylethanols. Tetrahedron: Asymmetry; 19: 2068-2071.
24. Ushio K, Hada J, Tanaka Y, Ebara K. 1993. Allyl bromide, a powerful inhibitor against R-enzyme activities in bakers'yeast reduction of ethyl 3-oxoalkanoates. Enzyme Microb Tech; 15: 222-228. (Pubitemid 23062282)
25. Yang ZH, Yao SJ, Lin DQ. 2004. Improving the stereoselectivity of asymmetric reduction of 3-oxo ester to 3-hydroxy ester with pretreatments on baker's yeast. Ind Eng Chem Res; 43: 4871-4875.