Recent developments in asymmetric reduction of ketones with biocatalysts

Tetrahedron: Asymmetry - Tập 14 Số 18 - Trang 2659-2681 - 2003
Kaoru Nakamura1, Rio Yamanaka1, Tomoko Matsuda2, Tadao Harada2
1Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan
2Department of Materials Chemistry, Faculty of Science and Technology, Ryukoku University, Otsu, Shiga 520-2194, Japan

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Santaniello, 2000, 95

Faber, 1995, 145

Hummel, 1989, Eur. J. Biochem., 184, 1, 10.1111/j.1432-1033.1989.tb14983.x

Nakamura, 2002, 991

Servi, 1990, Synthesis, 1, 10.1055/s-1990-26775

Roberts, 2000, J. Chem. Soc., Perkin Trans. 1, 611, 10.1039/a908303k

Roberts, 1999, J. Chem. Soc., Perkin Trans. 1, 1, 10.1039/a806595k

Roberts, 1998, J. Chem. Soc., Perkin Trans. 1, 157, 10.1039/a704412g

Azerad, 1995, Bull. Soc. Chim. Fr., 132, 17

Schomburg, D.; Salzmann, M. (GFB-Gesellschaft für Biotechnologische Forschung), Enzyme Handbook, Springer-Verlag, Berlin, D, 1990.

Bradshaw, 1992, J. Org. Chem., 57, 1526, 10.1021/jo00031a036

Bradshaw, 1992, J. Org. Chem., 57, 1532, 10.1021/jo00031a037

Nakamura, 1990, Bull. Chem. Soc. Jpn., 63, 1735, 10.1246/bcsj.63.1735

Nakamura, 1992, Chem. Lett., 951, 10.1246/cl.1992.951

Nakamura, 1988, Tetrahedron Lett., 29, 2453, 10.1016/S0040-4039(00)87905-8

Dutler, 1977, Eur. J. Biochem., 75, 423, 10.1111/j.1432-1033.1977.tb11544.x

Prelog, 1964, Pure Appl. Chem., 9, 119, 10.1351/pac196409010119

Jones, 1986, Tetrahedron, 42, 3351, 10.1016/S0040-4020(01)87306-3

Jones, 1976, 107

Davies, 1979, J. Am. Chem. Soc., 101, 5405, 10.1021/ja00512a048

Lam, 1988, J. Org. Chem., 53, 1611, 10.1021/jo00243a004

Velonia, 1999, Bioorg. Med. Chem. Lett., 9, 65, 10.1016/S0960-894X(98)00678-7

Zelinski, 1994, Bioorg. Med. Chem. Lett., 2, 421, 10.1016/0968-0896(94)80010-3

Nakamura, 2000, Tetrahedron Lett., 41, 6799, 10.1016/S0040-4039(00)01132-1

Nakamura, 2002, Chem. Commun., 1782, 10.1039/b203844g

Nakamura, 2002, Tetrahedron: Asymmetry, 13, 2529, 10.1016/S0957-4166(02)00683-3

Parkinson, 1984, Nature, 309, 148, 10.1038/309148a0

Yuan, 1997, J. Org. Chem., 62, 2494, 10.1021/jo9620573

Biade, 1992, J. Am. Chem. Soc., 114, 893, 10.1021/ja00029a015

Leonida, 1998, Bioorg. Med. Chem. Lett., 8, 2819, 10.1016/S0960-894X(98)00519-8

Kuwabata, 1993, Chem. Lett., 1631, 10.1246/cl.1993.1631

Kuwabata, 1994, J. Am. Chem. Soc., 116, 5437, 10.1021/ja00091a056

Sugimura, 1989, J. Am. Chem. Soc., 111, 2361, 10.1021/ja00188a093

Sugimura, 1990, Bioelectrochem. Bioenergetics., 24, 241, 10.1016/0302-4598(90)85025-D

Demirjian, 2000, 1

Yasohara, 1999, Appl. Microbiol. Biotechnol., 51, 847, 10.1007/s002530051472

Wada, 1998, Biosci. Biotech. Biochem., 62, 280, 10.1271/bbb.62.280

Wada, 1999, Biosci. Bioeng., 87, 144, 10.1016/S1389-1723(99)89003-3

Shimizu, 1984, Agric. Biol. Chem., 48, 2285, 10.1271/bbb1961.48.2285

Kataoka, 1990, Biotechnol. Lett., 12, 357, 10.1007/BF01024431

Miya, 1996, Biosci. Biotech. Biochem., 60, 95, 10.1271/bbb.60.95

Shafiee, 1998, Appl. Microbiol. Biotechnol., 49, 709, 10.1007/s002530051236

Kizaki, 2001, Appl. Microbiol. Biotechnol, 55, 590, 10.1007/s002530100599

Yasohara, 2000, Biosci. Biotech. Biochem., 64, 1430, 10.1271/bbb.64.1430

Yasohara, 2001, Tetrahedron: Asymmetry, 12, 1713, 10.1016/S0957-4166(01)00279-8

Kataoka, 1999, Appl. Microbiol. Biotechnol, 51, 486, 10.1007/s002530051421

Kita, 1999, Appl. Environ. Microbiol., 65, 5207, 10.1128/AEM.65.12.5207-5211.1999

Yoshisumi, 2001, Biosci. Biotech. Biochem., 65, 830, 10.1271/bbb.65.830

Wada, 1999, Appl. Environ. Microbiol., 65, 4399, 10.1128/AEM.65.10.4399-4403.1999

Kataoka, 2002, Biosci. Biotech. Biochem., 66, 2651, 10.1271/bbb.66.2651

Itoh, 1996, Biosci. Biotech. Biochem., 60, 1826, 10.1271/bbb.60.1826

Itoh, 1997, Appl. Environ. Microbiol., 63, 3783, 10.1128/AEM.63.10.3783-3788.1997

Itoh, 1999, J. Mol. Catal. B: Enzymatic, 6, 41, 10.1016/S1381-1177(98)00118-0

Wang, 1999, Appl. Microbiol. Biotechnol, 52, 386, 10.1007/s002530051536

Wang, 1999, Biosci. Biotech. Biochem., 63, 2216, 10.1271/bbb.63.2216

Itoh, 2002, Eur. J. Biochem., 269, 2394, 10.1046/j.1432-1033.2002.02899.x

Matsuyama, 2002, Org. Proc. Res. Develop., 6, 558, 10.1021/op025514s

Yamamoto, 2002, Biosci. Biotech. Biochem., 66, 481, 10.1271/bbb.66.481

Yamamoto, 2002, Biosci. Biotech. Biochem., 66, 925, 10.1271/bbb.66.925

Yamamoto, 2002, Biosci. Biotech. Biochem., 66, 1775, 10.1271/bbb.66.1775

Matsuyama, 2001, J. Mol. Catal. B: Enzymatic, 11, 513, 10.1016/S1381-1177(00)00032-1

Yamamoto, 1999, Biosci. Biotech. Biochem., 63, 1051, 10.1271/bbb.63.1051

Yamamoto, 1995, Biosci. Biotech. Biochem., 59, 1769, 10.1271/bbb.59.1769

Kayser, 1999, J. Org. Chem., 64, 6603, 10.1021/jo9900681

Rodrı̀guez, 2000, J. Org. Chem., 65, 2586, 10.1021/jo9917036

Rodrı̀guez, 2001, J. Am. Chem. Soc., 123, 1547, 10.1021/ja0027968

Allen, 2000, J. Protein Eng., 13, 5, 10.1093/protein/13.1.5

Nakayama, 1992, J. Am. Chem. Soc., 114, 780, 10.1021/ja00028a066

Hsieh, 1993, Science, 260, 337, 10.1126/science.10049109

Zhou, 1983, J. Am. Chem. Soc., 105, 5925, 10.1021/ja00356a041

Chen, 1984, Bioorg. Chem., 12, 98, 10.1016/0045-2068(84)90021-X

Shieh, 1985, J. Am. Chem. Soc., 107, 2993, 10.1021/ja00296a038

Fujisawa, 1984, Tetrahedron Lett., 25, 5083, 10.1016/S0040-4039(01)91125-6

Nakamura, 1984, Tetrahedron Lett., 25, 3979, 10.1016/0040-4039(84)80045-3

Ferraboschi, 1990, J. Chem. Soc., Perkin Trans. 1, 2469, 10.1039/p19900002469

Goodhue, 1986, 97

Nakamura, 1996, Tetrahedron Lett., 37, 1629, 10.1016/0040-4039(96)00073-1

Nakamura, 1998, J. Org. Chem., 63, 8957, 10.1021/jo9812779

Matsuda, 2000, Tetrahedron Lett., 41, 4135, 10.1016/S0040-4039(00)00552-9

Hamada, 2001, Biotechnol. Lett., 23, 1603, 10.1023/A:1011922823367

Matsuda, 2002, Tetrahedron: Asymmetry, 13, 971, 10.1016/S0957-4166(02)00226-4

Nakamura, 1996, Tetrahedron Lett., 37, 5727, 10.1016/0040-4039(96)01211-7

Nakamura, 1998, Tetrahedron, 54, 8393, 10.1016/S0040-4020(98)00439-6

Matsuda, 2000, J. Org. Chem., 65, 157, 10.1021/jo991283k

Nakamura, 2002, Chirality, 14, 703, 10.1002/chir.10129

Matsuda, 2000, Chem. Commun., 1367, 10.1039/b004069j

Matsuda, 2003, Chem. Commun., 1198, 10.1039/b301452e

Panza, 2002, Tetrahedron, 59, 4091, 10.1016/S0040-4020(02)00259-4

Howarth, 2001, Tetrahedron Lett., 42, 7517, 10.1016/S0040-4039(01)01601-X

Nakamura, 1993, Bull. Chem. Soc. Jpn., 66, 2738, 10.1246/bcsj.66.2738

Nakamura, 1995, Tetrahedron, 51, 687, 10.1016/0040-4020(94)00970-6

Nakamura, 1995, Tetrahedron Lett., 36, 265, 10.1016/0040-4039(94)02188-H

Nakamura, 1999, J. Chem. Soc., Perkin Trans. 1, 2397, 10.1039/a900936a

Nakamura, 1993, Tetrahedron: Asymmetry, 4, 1253, 10.1016/S0957-4166(00)80236-0

Nakamura, 1994, Bioorg. Med. Chem., 2, 433, 10.1016/0968-0896(94)80012-X

Zelinski, 1997, Biocatal. Biotransformation, 15, 57, 10.3109/10242429709003610

Anderson, 1995, J. Am. Chem. Soc., 117, 12358, 10.1021/ja00154a048

Nakamura, 2000, J. Chem. Soc., Perkin Trans. 1, 3205, 10.1039/b005204n

Nakamura, 2002, Tetrahedron Lett., 43, 3629, 10.1016/S0040-4039(02)00649-4

Conceicao, 2003, Tetrahedron: Asymmetry, 14, 43, 10.1016/S0957-4166(02)00798-X

D'Arrigo, 1997, Tetrahedron: Asymmetry, 8, 2375, 10.1016/S0957-4166(97)00257-7

D'Arrigo, 1998, Tetrahedron, 54, 15017, 10.1016/S0040-4020(98)00941-7

D'Arrigo, 1998, Tetrahedron: Asymmetry, 9, 4021, 10.1016/S0957-4166(98)00432-7

Nakamura, 1990, Tetrahedron Lett., 31, 267, 10.1016/S0040-4039(00)94389-2

Nakamura, 1987, Chem. Lett., 679, 10.1246/cl.1987.679

Nakamura, 1989, Tetrahedron Lett., 30, 2245, 10.1016/S0040-4039(00)99659-X

Dahl, 1999, Tetrahedron: Asymmetry, 10, 551, 10.1016/S0957-4166(99)00025-7

Nakamura, 1989, Bull. Chem. Soc. Jpn., 62, 875, 10.1246/bcsj.62.875

Forni, 1994, Tetrahedron, 50, 11995, 10.1016/S0040-4020(01)89310-8

Kim, 1992, Bull. Korean Chem. Soc., 13, 2

Hayakawa, 1998, Tetrahedron Lett., 39, 67, 10.1016/S0040-4039(97)10490-7

Ushio, 1993, Enzyme Microb. Technol., 15, 222, 10.1016/0141-0229(93)90141-N

Hayakawa, 1997, Tetrahedron: Asymmetry, 8, 3201, 10.1016/S0957-4166(97)00434-5

Nakamura, 1991, J. Org. Chem., 56, 4778, 10.1021/jo00015a038

Pham, 1989, J. Am. Chem. Soc., 111, 1935, 10.1021/ja00187a089

Zheng, 1994, Catal. Today, 22, 607, 10.1016/0920-5861(94)80126-6

Tripp, 1998, J. Am. Chem. Soc., 120, 5137, 10.1021/ja974129t

Heiss, 2001, J. Am. Chem. Soc., 123, 345, 10.1021/ja005575a

(a) Benedetti, F.; Forzato, C.; Nitti, P.; Pitacco, G.; Valentin, E.; Vicario, M. Tetrahedron: Asymmetry2001, 12, 505–511;

(b) Comasseto, J. V.; Omri, T.; Andrade, L. H.; Porto, A. L. M. Tetrahedron: Asymmetry2003, 14, 711–715;

(c) Sakai, A.; Bakke, M.; Ohta, H.; Kosugi, H.; Sugai, T. Chem. Lett.1999, 1255–1256;

(d) Ema, T.; Moriya, H.; Kofukuda, T.; Ishida, T.; Maehara, K.; Utaka, M.; Sakai, T. J. Org. Chem.2001, 66, 8682–8684.

Keinan, 1986, J. Am. Chem. Soc., 108, 162, 10.1021/ja00261a026

Keinan, 1986, J. Am. Chem. Soc., 108, 3474, 10.1021/ja00272a051

Keinan, 1992, J. Org. Chem., 57, 3631, 10.1021/jo00039a023

Kitazume, 1986, J. Org. Chem., 51, 2795, 10.1021/jo00364a034

Kitazume, 1987, Synthesis, 187, 10.1055/s-1987-27885

Kitazume, T.; Yamazaki T. In Selective Fluorination in Organic and Bioorganic Chemistry, ACS Symposium Series No. 456; Welch, J. T., Ed.; American Chemical Society, 1991; pp. 175–185

Kitazume, T.; Sato, T. J. Fluorine Chem.1985, 30, 189–202; 1996, 37, 3903–3906.

Fujisawa, 1993, Tetrahedron: Asymmetry, 4, 1237, 10.1016/S0957-4166(00)80234-7

Fujisawa, 1994, Tetrahedron: Asymmetry, 5, 1095, 10.1016/0957-4166(94)80060-X

Fujisawa, 1998, Tetrahedron, 54, 4267, 10.1016/S0040-4020(98)00144-6

Imuta, 1980, J. Org. Chem., 45, 3352, 10.1021/jo01304a044

Carvalho, 1991, Tetrahedron, 47, 2073, 10.1016/S0040-4020(01)96117-4

Wei, 1998, Tetrahedron, 54, 13059, 10.1016/S0040-4020(98)00796-0

Barbieri, 1999, Tetrahedron: Asymmetry, 10, 3931, 10.1016/S0957-4166(99)00402-4

Patel, 1992, J. Enzyme Microb. Technol., 14, 731, 10.1016/0141-0229(92)90113-3

Aragozzini, 1992, Biocatalysis, 5, 325, 10.3109/10242429209014878

Akakabe, 1995, J. Chem. Soc., Perkin Trans. 1, 1295, 10.1039/p19950001295

Drochner, 2001, Eur. J. Org. Chem., 211, 10.1002/1099-0690(200101)2001:1<211::AID-EJOC211>3.0.CO;2-R

Mori, K.; Mori, H. Org. Synth.1993, Coll. Vol. 8, 312–315

Mori, 1993, Liebigs Ann. Chem., 91, 10.1002/jlac.199319930115

Brooks, 1987, J. Org. Chem., 52, 3223, 10.1021/jo00391a009

Ohta, 1986, Agric. Biol. Chem., 50, 2499, 10.1271/bbb1961.50.2499

Bortolini, 1997, J. Org. Chem., 62, 1854, 10.1021/jo9618381

Fuhshuku, 2000, J. Org. Chem., 65, 129, 10.1021/jo991192n

Bel-Rhlid, 1992, Biocatalysis, 6, 319, 10.3109/10242429209065251

Ikeda, 1996, Tetrahedron, 52, 8113, 10.1016/0040-4020(96)00373-0

Zhu, 1996, Tetrahedron: Asymmetry, 7, 3295, 10.1016/0957-4166(96)00430-2

Lee, 1997, Tetrahedron: Asymmetry, 8, 3051, 10.1016/S0957-4166(97)00372-8

Besse, 1993, Bioorg. Chem., 21, 342, 10.1006/bioo.1993.1029

Nakamura, 1996, Tetrahedron: Asymmetry, 7, 409, 10.1016/0957-4166(96)00020-1

Sakakibara, 1995, Biosci. Biotech. Biochem., 59, 1300, 10.1271/bbb.59.1300

Levene, P. A.; Walti, A. Org. Synth.1943, Coll. Vol. 2, 545–547

Barry, 1981, Synthesis, 453, 10.1055/s-1981-29479

Ramaswamy, 1991, Tetrahedron, 47, 1145, 10.1016/S0040-4020(01)86371-7

Ferraboschi, 1990, J. Chem. Soc., Perkin 1, 2469, 10.1039/p19900002469

Sato, 1988, Chem. Lett., 1537, 10.1246/cl.1988.1537

Wei, 2000, Bioorg. Med. Chem., 8, 1129, 10.1016/S0968-0896(00)00023-7

Kodama, 1990, Tetrahedron Lett., 31, 4025, 10.1016/S0040-4039(00)94489-7

Iriuchijima, 1978, Agric. Biol. Chem., 22, 451, 10.1271/bbb1961.42.451

Liu, 1995, J. Org. Chem., 60, 2022, 10.1021/jo00112a025

Fujisawa, 1985, Chem. Lett., 1751, 10.1246/cl.1985.1751

Itoh, 1986, Tetrahedron Lett., 27, 5405, 10.1016/S0040-4039(00)85223-5

Robin, 1993, Tetrahedron: Asymmetry, 4, 239, 10.1016/S0957-4166(00)82344-7

Gopalan, 1990, Tetrahedron Lett., 31, 5575, 10.1016/S0040-4039(00)97900-0

Ohtsuka, 1997, Bull. Chem. Soc. Jpn., 70, 483, 10.1246/bcsj.70.483

Ohta, 1987, J. Org. Chem., 52, 2735, 10.1021/jo00389a018