메뉴 건너뛰기




Volumn 83, Issue 11, 2008, Pages 1479-1485

Yeast-mediated enantioselective synthesis of chiral R-(+)- and S-(-)-1-phenyl-1-butanol from prochiral phenyl n-propyl ketone in hexane-water biphasic culture

Author keywords

Candida utilis; Hexane water biphasic culture; ; Phenyl n propyl ketone; R,S 1 phenyl 1 butanol; Saccharomyces cerevisiae; Zn2+ ion

Indexed keywords

ALCOHOLS; CELL GROWTH; ELECTRON TRANSITIONS; ENANTIOSELECTIVITY; GROWTH (MATERIALS); GROWTH KINETICS; HEXANE; IONS; KETONES; ORGANIC COMPOUNDS; PH EFFECTS; YEAST; ZINC;

EID: 57149089684     PISSN: 02682575     EISSN: 10974660     Source Type: Journal    
DOI: 10.1002/jctb.1930     Document Type: Article
Times cited : (9)

References (32)
  • 1
    • 12044253833 scopus 로고
    • Baker's yeast mediated transformations in organic chemistry
    • Csuk R and Glänzer BI, Baker's yeast mediated transformations in organic chemistry. Chem Rev 91:49-97 (1991).
    • (1991) Chem Rev , vol.91 , pp. 49-97
    • Csuk, R.1    Glänzer, B.I.2
  • 2
    • 4243794106 scopus 로고
    • The biocatalytic approach to the preparation of enantiomerically pure chiral building blocks
    • Santaniello E, Ferraboschi P, Grisenti P and Manzocchi A, The biocatalytic approach to the preparation of enantiomerically pure chiral building blocks. Chem Rev 92:1071-1140 (1992).
    • (1992) Chem Rev , vol.92 , pp. 1071-1140
    • Santaniello, E.1    Ferraboschi, P.2    Grisenti, P.3    Manzocchi, A.4
  • 3
    • 4243365905 scopus 로고
    • Application of baker's yeast in bioorganic synthesis
    • Ward OP, Application of baker's yeast in bioorganic synthesis. Can J Bot 73:1043-1048 (1995).
    • (1995) Can J Bot , vol.73 , pp. 1043-1048
    • Ward, O.P.1
  • 4
    • 0344352483 scopus 로고    scopus 로고
    • Chemoenzymatic synthesis of (R)-(+)-2-methylbutan-1-ol, a chiral synthon for the preparation of optically active pheromones
    • Geresh S, Valiyaveettil TJ, Lavie Y and Shani A, Chemoenzymatic synthesis of (R)-(+)-2-methylbutan-1-ol, a chiral synthon for the preparation of optically active pheromones. Tetrahedron Asymmetry 9:89-96 (1998).
    • (1998) Tetrahedron Asymmetry , vol.9 , pp. 89-96
    • Geresh, S.1    Valiyaveettil, T.J.2    Lavie, Y.3    Shani, A.4
  • 5
    • 1242315612 scopus 로고    scopus 로고
    • Biotransformation of (±)-α-ionone and β-ionone by cultured cells of Caragana chamlagu
    • Sakamaki H, Itoh KI, Chai W, Hayashida Y, Kitanaka S and Horiuchi CA, Biotransformation of (±)-α-ionone and β-ionone by cultured cells of Caragana chamlagu. J Mol Catal B 27:177-181 (2004).
    • (2004) J Mol Catal B , vol.27 , pp. 177-181
    • Sakamaki, H.1    Itoh, K.I.2    Chai, W.3    Hayashida, Y.4    Kitanaka, S.5    Horiuchi, C.A.6
  • 6
    • 7244227658 scopus 로고    scopus 로고
    • Danish IA and Prasad KJR, Reduction of 1-hydroxyimino- 1,2,3,4-tetrahydro-carbazoles by metal and Baker's yeast: syntheses of aminocarbazole derivatives. Z Naturforsch 59:1054-1058 (2004).
    • Danish IA and Prasad KJR, Reduction of 1-hydroxyimino- 1,2,3,4-tetrahydro-carbazoles by metal and Baker's yeast: syntheses of aminocarbazole derivatives. Z Naturforsch 59:1054-1058 (2004).
  • 7
    • 0345742698 scopus 로고    scopus 로고
    • Enantioselective bioreduction of acetophenone and its analogous by the fungus Trichothecium sp
    • Mandal D, Ahmad A, Islam Khan M and Kumar R, Enantioselective bioreduction of acetophenone and its analogous by the fungus Trichothecium sp. J Mol Catal B 27:61-63 (2004).
    • (2004) J Mol Catal B , vol.27 , pp. 61-63
    • Mandal, D.1    Ahmad, A.2    Islam Khan, M.3    Kumar, R.4
  • 9
    • 0035177201 scopus 로고    scopus 로고
    • Enantioselective synthesis of both enantiomers of various propargylic alcohols by use of two oxidoreductases
    • Schubert T, Hummel W, Kula M and Müller M, Enantioselective synthesis of both enantiomers of various propargylic alcohols by use of two oxidoreductases. Eur J Org Chem 22:4181-4187 (2001).
    • (2001) Eur J Org Chem , vol.22 , pp. 4181-4187
    • Schubert, T.1    Hummel, W.2    Kula, M.3    Müller, M.4
  • 11
    • 3042582109 scopus 로고    scopus 로고
    • Behaviour of dehydrated baker's yeast during reduction reactions in a biphasic medium
    • Cappaert L and Larroche C, Behaviour of dehydrated baker's yeast during reduction reactions in a biphasic medium. Appl Microbiol Biotechnol 64:686-690 (2004).
    • (2004) Appl Microbiol Biotechnol , vol.64 , pp. 686-690
    • Cappaert, L.1    Larroche, C.2
  • 12
    • 0000430160 scopus 로고    scopus 로고
    • Highly enantioselective reduction of carbonyl compounds using a reductase purified from bakers' yeast
    • Ema T, Sugiyama Y, Fukumoto M, Moriya H, Cui JN, Sakai T, et al., Highly enantioselective reduction of carbonyl compounds using a reductase purified from bakers' yeast. J Org Chem 63:4996-5000 (1998).
    • (1998) J Org Chem , vol.63 , pp. 4996-5000
    • Ema, T.1    Sugiyama, Y.2    Fukumoto, M.3    Moriya, H.4    Cui, J.N.5    Sakai, T.6
  • 13
    • 0028260855 scopus 로고
    • Highly efficient enzymic asymmetric reduction by use of regenerating NADPH in bakers' yeast cell-free extract
    • Ishihara K, Sakai T, Tsuboi S and Utaka M, Highly efficient enzymic asymmetric reduction by use of regenerating NADPH in bakers' yeast cell-free extract. Tetrahedron Lett 35:4569-4570 (1994).
    • (1994) Tetrahedron Lett , vol.35 , pp. 4569-4570
    • Ishihara, K.1    Sakai, T.2    Tsuboi, S.3    Utaka, M.4
  • 14
    • 0032127795 scopus 로고    scopus 로고
    • Asymmetric reduction of acetophenone with calcium-alginate-entrapped baker's yeast in organic solvents
    • Griffin DR, Yang F, Carta G and Gainer JL, Asymmetric reduction of acetophenone with calcium-alginate-entrapped baker's yeast in organic solvents. Biotechnol Prog 14:588-593 (1998).
    • (1998) Biotechnol Prog , vol.14 , pp. 588-593
    • Griffin, D.R.1    Yang, F.2    Carta, G.3    Gainer, J.L.4
  • 15
    • 0035980561 scopus 로고    scopus 로고
    • Immobilization of yeast alcohol dehydrogenase by entrapment and covalent binding to polymeric supports
    • Soni S, Desai JD and Devi S, Immobilization of yeast alcohol dehydrogenase by entrapment and covalent binding to polymeric supports. J Appl Polym Sci 82:1299-1305 (2001).
    • (2001) J Appl Polym Sci , vol.82 , pp. 1299-1305
    • Soni, S.1    Desai, J.D.2    Devi, S.3
  • 16
    • 0034944766 scopus 로고    scopus 로고
    • Asymmetric reduction of aromatic ketones by the baker's yeast in organic solvent systems
    • Liu X, Zhu TS, Sun PD and Xu JH, Asymmetric reduction of aromatic ketones by the baker's yeast in organic solvent systems. Synth Commun 31:1521-1526 (2001).
    • (2001) Synth Commun , vol.31 , pp. 1521-1526
    • Liu, X.1    Zhu, T.S.2    Sun, P.D.3    Xu, J.H.4
  • 17
    • 0035108407 scopus 로고    scopus 로고
    • Enzymes which are stable in the presence of organic solvents
    • Ogino H and Ishikawa H, Enzymes which are stable in the presence of organic solvents. J Biosci Bioeng 91:109-116 (2001).
    • (2001) J Biosci Bioeng , vol.91 , pp. 109-116
    • Ogino, H.1    Ishikawa, H.2
  • 18
    • 0037182273 scopus 로고    scopus 로고
    • Tolerance of immobilized baker's yeast in organic solvents
    • Qun J, Shanjing Y and Lehe M, Tolerance of immobilized baker's yeast in organic solvents. Enzyme Microb Technol 30:721-725 (2002).
    • (2002) Enzyme Microb Technol , vol.30 , pp. 721-725
    • Qun, J.1    Shanjing, Y.2    Lehe, M.3
  • 20
    • 0023385987 scopus 로고
    • Rules for optimization of biocatalysis in organic solvents
    • Laane C, Boeren S, Vos K and Veeger C, Rules for optimization of biocatalysis in organic solvents. Biotechnol Bioeng 30:81-87 (1987).
    • (1987) Biotechnol Bioeng , vol.30 , pp. 81-87
    • Laane, C.1    Boeren, S.2    Vos, K.3    Veeger, C.4
  • 21
    • 84985684413 scopus 로고
    • Biotransformation of benzaldehyde to benzyl alcohol by whole cells and cell extracts of bakers' yeast in two-phase systems
    • Nikolova P and Ward OP, Biotransformation of benzaldehyde to benzyl alcohol by whole cells and cell extracts of bakers' yeast in two-phase systems. Prog Biotechnol 8:667-673 (1992).
    • (1992) Prog Biotechnol , vol.8 , pp. 667-673
    • Nikolova, P.1    Ward, O.P.2
  • 22
    • 0032493833 scopus 로고    scopus 로고
    • Control of enantioselectivity in the baker's yeast asymmetric reduction of γ-chloro β-diketones to γ-chloro (S)-β-hydroxy ketones
    • Cui J, Ema T, Sakai T and Utaka M, Control of enantioselectivity in the baker's yeast asymmetric reduction of γ-chloro β-diketones to γ-chloro (S)-β-hydroxy ketones. Tetrahedron Asymmetry 9:2681-2692 (1998).
    • (1998) Tetrahedron Asymmetry , vol.9 , pp. 2681-2692
    • Cui, J.1    Ema, T.2    Sakai, T.3    Utaka, M.4
  • 23
    • 0011247696 scopus 로고    scopus 로고
    • Enantioselective synthesis of S-(-)-1-phenylethanol in Candida utilis semi-fed-batch cultures
    • Cheng C and Ma JH, Enantioselective synthesis of S-(-)-1-phenylethanol in Candida utilis semi-fed-batch cultures. Proc Biochem 31:119-124 (1996).
    • (1996) Proc Biochem , vol.31 , pp. 119-124
    • Cheng, C.1    Ma, J.H.2
  • 24
    • 0031588695 scopus 로고    scopus 로고
    • Glucose metabolism and bioreduction of 2-butanone by Candida utilis studied by means of ion-exchange chromatography
    • Cheng C and Ma JH, Glucose metabolism and bioreduction of 2-butanone by Candida utilis studied by means of ion-exchange chromatography. J Chromatrogr A 763:205-211 (1997).
    • (1997) J Chromatrogr A , vol.763 , pp. 205-211
    • Cheng, C.1    Ma, J.H.2
  • 25
    • 0345256290 scopus 로고    scopus 로고
    • Column switching technique, assisted on-line matrix elimination, and chiral analysis of R- and S-1-phenyl-1-butanol in biphasic Saccharomyces cerevisiae mediated culture
    • Tsai SR and Cheng C, Column switching technique, assisted on-line matrix elimination, and chiral analysis of R- and S-1-phenyl-1-butanol in biphasic Saccharomyces cerevisiae mediated culture. J Liq Chromatogr Relat Technol 26:3249-3264 (2003).
    • (2003) J Liq Chromatogr Relat Technol , vol.26 , pp. 3249-3264
    • Tsai, S.R.1    Cheng, C.2
  • 26
    • 0021475287 scopus 로고
    • Microbial asymmetric catalysis: Enantioselective reduction of ketones
    • Sih C and Chen C, Microbial asymmetric catalysis: enantioselective reduction of ketones. Angew Chem Int Ed Engl 23:570-578 (1984).
    • (1984) Angew Chem Int Ed Engl , vol.23 , pp. 570-578
    • Sih, C.1    Chen, C.2
  • 27
    • 0029819664 scopus 로고    scopus 로고
    • Alkaline unfolding and salt-induced folding of yeast alcohol dehydrogenase under high pH conditions
    • Le WP, Yan SX, Li S, Zhong HN and Zhou HM, Alkaline unfolding and salt-induced folding of yeast alcohol dehydrogenase under high pH conditions. Int J Pept Protein Res 47:484-490 (1996).
    • (1996) Int J Pept Protein Res , vol.47 , pp. 484-490
    • WP, L.1    Yan, S.X.2    Li, S.3    Zhong, H.N.4    Zhou, H.M.5
  • 28
    • 0029892434 scopus 로고    scopus 로고
    • Acid-induced folding of yeast alcohol dehydrogenase under low pH conditions
    • Le WP, Yan SX, Zhang YX and Zhou HM, Acid-induced folding of yeast alcohol dehydrogenase under low pH conditions. J Biochem 119:674-679 (1996).
    • (1996) J Biochem , vol.119 , pp. 674-679
    • WP, L.1    Yan, S.X.2    Zhang, Y.X.3    Zhou, H.M.4
  • 30
    • 0036891388 scopus 로고    scopus 로고
    • The three zinc-containing alcohol dehydrogenases from baker's yeast, Saccharomyces cerevisiae
    • Leskovac V, Trivić S and Peričin D, The three zinc-containing alcohol dehydrogenases from baker's yeast, Saccharomyces cerevisiae. FEMS Yeast Res 2:481-494 (2002).
    • (2002) FEMS Yeast Res , vol.2 , pp. 481-494
    • Leskovac, V.1    Trivić, S.2    Peričin, D.3
  • 31
    • 0031937470 scopus 로고    scopus 로고
    • Use of competitive dead-end inhibitors to determine the chemical mechanism of action of yeast alcohol dehydrogenase
    • Leskovac V, Trivić S and Anderson BM, Use of competitive dead-end inhibitors to determine the chemical mechanism of action of yeast alcohol dehydrogenase. Mol Cell Biochem 178:219-227 (1998).
    • (1998) Mol Cell Biochem , vol.178 , pp. 219-227
    • Leskovac, V.1    Trivić, S.2    Anderson, B.M.3
  • 32
    • 0026675661 scopus 로고
    • Importance of the structural zinc atom for the stability of yeast alcohol dehydrogenase
    • Magonet E, Hayen P, Delforge D, Delaive E and Remacle J, Importance of the structural zinc atom for the stability of yeast alcohol dehydrogenase. Biochem J 287:361-365 (1992).
    • (1992) Biochem J , vol.287 , pp. 361-365
    • Magonet, E.1    Hayen, P.2    Delforge, D.3    Delaive, E.4    Remacle, J.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.