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Volumn 343, Issue 6-7, 2001, Pages 547-558

Enzymatic Routes to Enantiomerically Pure Aromatic α-Hydroxy Carboxylic Acids: A Further Example for the Diversity of Biocatalysis

Author keywords

Asymmetric catalysis; Asymmetric synthesis; Carboxylic acids; Chiral resolution; Cyanohydrins

Indexed keywords


EID: 0041590743     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/1615-4169(200108)343:6/7<547::aid-adsc547>3.0.co;2-a     Document Type: Review
Times cited : (192)

References (87)
  • 1
    • 0006112560 scopus 로고    scopus 로고
    • 2nd Edn., Wiley-VCH, Weinheim
    • For a comprehensive overview about biotransformations in general, see: (a) H.-J. Rehm, G. Reed, A. Pühler, P. Stadler, D. R. Kelly, Biotechnology: Biotranformations I and II, Vols. 8a and 8b, 2nd Edn., Wiley-VCH, Weinheim, 1998; (b) K. Faber, Biotransformations in Organic Chemistry, Springer, Berlin, 1997; (c) A. Liese, K. Seelbach, C. Wandrey, Industrial Biotransformations, Wiley-VCH, Weinheim, 2000.
    • (1998) Biotechnology: Biotranformations I and II , vol.8 A AND B
    • Rehm, H.-J.1    Reed, G.2    Pühler, A.3    Stadler, P.4    Kelly, D.R.5
  • 2
    • 0003479152 scopus 로고    scopus 로고
    • Springer, Berlin
    • For a comprehensive overview about biotransformations in general, see: (a) H.-J. Rehm, G. Reed, A. Pühler, P. Stadler, D. R. Kelly, Biotechnology: Biotranformations I and II, Vols. 8a and 8b, 2nd Edn., Wiley-VCH, Weinheim, 1998; (b) K. Faber, Biotransformations in Organic Chemistry, Springer, Berlin, 1997; (c) A. Liese, K. Seelbach, C. Wandrey, Industrial Biotransformations, Wiley-VCH, Weinheim, 2000.
    • (1997) Biotransformations in Organic Chemistry
    • Faber, K.1
  • 3
    • 0004173474 scopus 로고    scopus 로고
    • Wiley-VCH, Weinheim
    • For a comprehensive overview about biotransformations in general, see: (a) H.-J. Rehm, G. Reed, A. Pühler, P. Stadler, D. R. Kelly, Biotechnology: Biotranformations I and II, Vols. 8a and 8b, 2nd Edn., Wiley-VCH, Weinheim, 1998; (b) K. Faber, Biotransformations in Organic Chemistry, Springer, Berlin, 1997; (c) A. Liese, K. Seelbach, C. Wandrey, Industrial Biotransformations, Wiley-VCH, Weinheim, 2000.
    • (2000) Industrial Biotransformations
    • Liese, A.1    Seelbach, K.2    Wandrey, C.3
  • 5
    • 0033599540 scopus 로고    scopus 로고
    • For the asymmetric synthesis of chiral cyanohydrins (as precursors) via metal-catalysts and organocatalysts, see: (a) Y. Hamashima, D. Sawada, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 1999, 121, 2641; (b) D. Sawada, M. Shibasaki, Angew. Chem. 2000, 112, 215; Angew. Chem. Int. Ed. Engl. 2000, 39, 209; (c) M. Kanai, Y. Hamashima, M. Shibasaki, Tetrahedron Lett. 2000, 41, 2405; (d) Y. Hamashima, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2000, 122, 7412; (e) Y. Hamashima, M. Kanai, M Shibasaki, Tetrahedron Lett. 2001, 42, 691; (f) K. Tanaka, A. Mori, S. Inoue, J. Org. Chem. 1990, 55, 181; (g) A. Mori, H. Nitta, M. Kudo, S. Inoue, Tetrahedron Lett. 1991, 32, 4333.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 2641
    • Hamashima, Y.1    Sawada, D.2    Kanai, M.3    Shibasaki, M.4
  • 6
    • 0001435240 scopus 로고    scopus 로고
    • For the asymmetric synthesis of chiral cyanohydrins (as precursors) via metal-catalysts and organocatalysts, see: (a) Y. Hamashima, D. Sawada, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 1999, 121, 2641; (b) D. Sawada, M. Shibasaki, Angew. Chem. 2000, 112, 215; Angew. Chem. Int. Ed. Engl. 2000, 39, 209; (c) M. Kanai, Y. Hamashima, M. Shibasaki, Tetrahedron Lett. 2000, 41, 2405; (d) Y. Hamashima, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2000, 122, 7412; (e) Y. Hamashima, M. Kanai, M Shibasaki, Tetrahedron Lett. 2001, 42, 691; (f) K. Tanaka, A. Mori, S. Inoue, J. Org. Chem. 1990, 55, 181; (g) A. Mori, H. Nitta, M. Kudo, S. Inoue, Tetrahedron Lett. 1991, 32, 4333.
    • (2000) Angew. Chem. , vol.112 , pp. 215
    • Sawada, D.1    Shibasaki, M.2
  • 7
    • 0034598534 scopus 로고    scopus 로고
    • For the asymmetric synthesis of chiral cyanohydrins (as precursors) via metal-catalysts and organocatalysts, see: (a) Y. Hamashima, D. Sawada, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 1999, 121, 2641; (b) D. Sawada, M. Shibasaki, Angew. Chem. 2000, 112, 215; Angew. Chem. Int. Ed. Engl. 2000, 39, 209; (c) M. Kanai, Y. Hamashima, M. Shibasaki, Tetrahedron Lett. 2000, 41, 2405; (d) Y. Hamashima, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2000, 122, 7412; (e) Y. Hamashima, M. Kanai, M Shibasaki, Tetrahedron Lett. 2001, 42, 691; (f) K. Tanaka, A. Mori, S. Inoue, J. Org. Chem. 1990, 55, 181; (g) A. Mori, H. Nitta, M. Kudo, S. Inoue, Tetrahedron Lett. 1991, 32, 4333.
    • (2000) Angew. Chem. Int. Ed. Engl. , vol.39 , pp. 209
  • 8
    • 0034175598 scopus 로고    scopus 로고
    • For the asymmetric synthesis of chiral cyanohydrins (as precursors) via metal-catalysts and organocatalysts, see: (a) Y. Hamashima, D. Sawada, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 1999, 121, 2641; (b) D. Sawada, M. Shibasaki, Angew. Chem. 2000, 112, 215; Angew. Chem. Int. Ed. Engl. 2000, 39, 209; (c) M. Kanai, Y. Hamashima, M. Shibasaki, Tetrahedron Lett. 2000, 41, 2405; (d) Y. Hamashima, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2000, 122, 7412; (e) Y. Hamashima, M. Kanai, M Shibasaki, Tetrahedron Lett. 2001, 42, 691; (f) K. Tanaka, A. Mori, S. Inoue, J. Org. Chem. 1990, 55, 181; (g) A. Mori, H. Nitta, M. Kudo, S. Inoue, Tetrahedron Lett. 1991, 32, 4333.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 2405
    • Kanai, M.1    Hamashima, Y.2    Shibasaki, M.3
  • 9
    • 0034596326 scopus 로고    scopus 로고
    • For the asymmetric synthesis of chiral cyanohydrins (as precursors) via metal-catalysts and organocatalysts, see: (a) Y. Hamashima, D. Sawada, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 1999, 121, 2641; (b) D. Sawada, M. Shibasaki, Angew. Chem. 2000, 112, 215; Angew. Chem. Int. Ed. Engl. 2000, 39, 209; (c) M. Kanai, Y. Hamashima, M. Shibasaki, Tetrahedron Lett. 2000, 41, 2405; (d) Y. Hamashima, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2000, 122, 7412; (e) Y. Hamashima, M. Kanai, M Shibasaki, Tetrahedron Lett. 2001, 42, 691; (f) K. Tanaka, A. Mori, S. Inoue, J. Org. Chem. 1990, 55, 181; (g) A. Mori, H. Nitta, M. Kudo, S. Inoue, Tetrahedron Lett. 1991, 32, 4333.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 7412
    • Hamashima, Y.1    Kanai, M.2    Shibasaki, M.3
  • 10
    • 0035931483 scopus 로고    scopus 로고
    • For the asymmetric synthesis of chiral cyanohydrins (as precursors) via metal-catalysts and organocatalysts, see: (a) Y. Hamashima, D. Sawada, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 1999, 121, 2641; (b) D. Sawada, M. Shibasaki, Angew. Chem. 2000, 112, 215; Angew. Chem. Int. Ed. Engl. 2000, 39, 209; (c) M. Kanai, Y. Hamashima, M. Shibasaki, Tetrahedron Lett. 2000, 41, 2405; (d) Y. Hamashima, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2000, 122, 7412; (e) Y. Hamashima, M. Kanai, M Shibasaki, Tetrahedron Lett. 2001, 42, 691; (f) K. Tanaka, A. Mori, S. Inoue, J. Org. Chem. 1990, 55, 181; (g) A. Mori, H. Nitta, M. Kudo, S. Inoue, Tetrahedron Lett. 1991, 32, 4333.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 691
    • Hamashima, Y.1    Kanai, M.2    Shibasaki, M.3
  • 11
    • 0000624398 scopus 로고
    • For the asymmetric synthesis of chiral cyanohydrins (as precursors) via metal-catalysts and organocatalysts, see: (a) Y. Hamashima, D. Sawada, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 1999, 121, 2641; (b) D. Sawada, M. Shibasaki, Angew. Chem. 2000, 112, 215; Angew. Chem. Int. Ed. Engl. 2000, 39, 209; (c) M. Kanai, Y. Hamashima, M. Shibasaki, Tetrahedron Lett. 2000, 41, 2405; (d) Y. Hamashima, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2000, 122, 7412; (e) Y. Hamashima, M. Kanai, M Shibasaki, Tetrahedron Lett. 2001, 42, 691; (f) K. Tanaka, A. Mori, S. Inoue, J. Org. Chem. 1990, 55, 181; (g) A. Mori, H. Nitta, M. Kudo, S. Inoue, Tetrahedron Lett. 1991, 32, 4333.
    • (1990) J. Org. Chem. , vol.55 , pp. 181
    • Tanaka, K.1    Mori, A.2    Inoue, S.3
  • 12
    • 0025780990 scopus 로고
    • For the asymmetric synthesis of chiral cyanohydrins (as precursors) via metal-catalysts and organocatalysts, see: (a) Y. Hamashima, D. Sawada, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 1999, 121, 2641; (b) D. Sawada, M. Shibasaki, Angew. Chem. 2000, 112, 215; Angew. Chem. Int. Ed. Engl. 2000, 39, 209; (c) M. Kanai, Y. Hamashima, M. Shibasaki, Tetrahedron Lett. 2000, 41, 2405; (d) Y. Hamashima, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2000, 122, 7412; (e) Y. Hamashima, M. Kanai, M Shibasaki, Tetrahedron Lett. 2001, 42, 691; (f) K. Tanaka, A. Mori, S. Inoue, J. Org. Chem. 1990, 55, 181; (g) A. Mori, H. Nitta, M. Kudo, S. Inoue, Tetrahedron Lett. 1991, 32, 4333.
    • (1991) Tetrahedron Lett. , vol.32 , pp. 4333
    • Mori, A.1    Nitta, H.2    Kudo, M.3    Inoue, S.4
  • 13
    • 0030997203 scopus 로고    scopus 로고
    • An asymmetric approach to aromatic α-hydroxy carboxylic acid derivatives via metal-based asymmetric catalytic hydrogenation of keto acids has been developed by: (a) J.-F. Carpentier, A. Mortreux, Tetrahedron: Asymmetry 1997, 8, 1083; (b) C. Pasquier, S. Naili, L. Pelinski, J. Brocard, A. Mortreux, F. Agbossou, Tetrahedron: Asymmetry 1998, 9, 193.
    • (1997) Tetrahedron: Asymmetry , vol.8 , pp. 1083
    • Mortreux, A.1
  • 14
    • 0032579306 scopus 로고    scopus 로고
    • An asymmetric approach to aromatic α-hydroxy carboxylic acid derivatives via metal-based asymmetric catalytic hydrogenation of keto acids has been developed by: (a) J.-F. Carpentier, A. Mortreux, Tetrahedron: Asymmetry 1997, 8, 1083; (b) C. Pasquier, S. Naili, L. Pelinski, J. Brocard, A. Mortreux, F. Agbossou, Tetrahedron: Asymmetry 1998, 9, 193.
    • (1998) Tetrahedron: Asymmetry , vol.9 , pp. 193
    • Pasquier, C.1    Naili, S.2    Pelinski, L.3    Brocard, J.4    Mortreux, A.5    Agbossou, F.6
  • 15
    • 0003445429 scopus 로고    scopus 로고
    • Springer, Berlin
    • Several metal-catalytic asymmetric routes for the synthesis of aromatic α-hydroxy carboxylic acids or chiral precursors thereof are discussed in: (a) E. N. Jacobsen, A. Pfaltz, H. Yamamoto (Eds.), Comprehensive Asymmetric Catalysis I-III, Springer, Berlin, 1999; (b) I. Ojima (Ed.), Catalytic Asymmetric Synthesis, 2. Ed., Wiley-VCH, New York, 2000.
    • (1999) Comprehensive Asymmetric Catalysis I-III
    • Jacobsen, E.N.1    Pfaltz, A.2    Yamamoto, H.3
  • 16
    • 84891580093 scopus 로고    scopus 로고
    • Wiley-VCH, New York
    • Several metal-catalytic asymmetric routes for the synthesis of aromatic α-hydroxy carboxylic acids or chiral precursors thereof are discussed in: (a) E. N. Jacobsen, A. Pfaltz, H. Yamamoto (Eds.), Comprehensive Asymmetric Catalysis I-III, Springer, Berlin, 1999; (b) I. Ojima (Ed.), Catalytic Asymmetric Synthesis, 2. Ed., Wiley-VCH, New York, 2000.
    • (2000) Catalytic Asymmetric Synthesis, 2. Ed.
    • Ojima, I.1
  • 23
    • 85087226590 scopus 로고    scopus 로고
    • [1b], p. 59ff
    • [1b], p. 59ff.
  • 38
    • 0347399094 scopus 로고    scopus 로고
    • EP 666320, 1995
    • Y. Hashimoto (Nitto Chemical Industry), EP 666320, 1995.
    • Hashimoto, Y.1
  • 39
    • 0348029911 scopus 로고    scopus 로고
    • Nitto Chemical Industry, EP 711836, 1996
    • K. Tamura (Nitto Chemical Industry), EP 711836, 1996.
    • Tamura, K.1
  • 43
    • 0348029910 scopus 로고    scopus 로고
    • US Patent 5241087, 1993
    • P. van Eikeren, US Patent 5241087, 1993.
    • Van Eikeren, P.1
  • 46
    • 0000710861 scopus 로고
    • F. Effenberger, Angew. Chem. 1994, 106, 1609; Angew. Chem. Int. Ed. Engl. 1994, 33, 1555.
    • (1994) Angew. Chem. , vol.106 , pp. 1609
    • Effenberger, F.1
  • 47
    • 33748215202 scopus 로고
    • F. Effenberger, Angew. Chem. 1994, 106, 1609; Angew. Chem. Int. Ed. Engl. 1994, 33, 1555.
    • (1994) Angew. Chem. Int. Ed. Engl. , vol.33 , pp. 1555
  • 53
    • 84985534669 scopus 로고
    • F. Effenberger, T. Ziegler, S. Förster, Angew. Chem. 1987, 99, 491; Angew. Chem. Int. Ed. Engl. 1987, 26, 458.
    • (1987) Angew. Chem. Int. Ed. Engl. , vol.26 , pp. 458
  • 58
    • 33748630895 scopus 로고    scopus 로고
    • S. Förster, J. Roos, F. Effenberger, H. Wajant, H. Sprauer, Angew. Chem. 1996, 108, 493; Angew. Chem. Int. Ed. Engl. 1996, 35, 437.
    • (1996) Angew. Chem. Int. Ed. Engl. , vol.35 , pp. 437
  • 59
    • 25944441641 scopus 로고
    • Ph. D. Thesis, University of Stuttgart
    • B. Hörsch, Ph. D. Thesis, University of Stuttgart, 1990.
    • (1990)
    • Hörsch, B.1
  • 68
    • 0025253111 scopus 로고
    • U. Niedermeyer, M. R. Kula, Angew. Chem. 1990, 102, 423; Angew. Chem. Int. Ed. Engl. 1990, 29, 386.
    • (1990) Angew. Chem. Int. Ed. Engl. , vol.29 , pp. 386
  • 80
    • 0348029905 scopus 로고    scopus 로고
    • (Ed.: R. N. Patel), Marcel Dekker Inc., New York, chapter 12
    • F. Effenberger, in Stereoselective Biocatalysis (Ed.: R. N. Patel), Marcel Dekker Inc., New York, 2000, chapter 12, p. 332.
    • (2000) Stereoselective Biocatalysis , pp. 332
    • Effenberger, F.1


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