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Enantioselective Biotransformations of Nitriles in Organic Synthesis

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Abstract

Recent advances in enantioselective biotransformations of nitriles utilizing nitrile-hydrolyzing microorganisms and enzymes are summarized in this article. Various examples of biocatalytic synthesis of highly enantiopure carboxylic acids including amino acids, hydroxyl acids, cyclopropanecarboxylic acids and amide derivatives and oxiranecarboxamides are presented. The enantioselectivity of the nitrile hydratases, nitrilases and amideses is discussed.

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References

  1. For reviews of biodegradation of nitriles, see (a) Cyanide Compounds in Biology (Ciba Foundation Symposium 140), ed. D.␣Evgred and S. Harnett (Wiley, Chichester, 1998); (b) J.-C. Jallageas, A. Arnaud and P. Galzy, Adv. Biochem. Eng. 12, (1980), 1; (c) J.L. Legras, G. Chuzel, A. Arnaud and P. Galzy, World J, Microbiol, Biotechnol. 6, (1990), 83.

  2. (a) K.V. Thimann and S. Mahadevan, Arch. Biochem. Biophy. 105, (1964), 133; (b) S. Mahadevan and K.V. Thimann, Arch. Biochem, Biophy. 107, (1964), 62; (c) D. B. Harper, Biochem. Soc. Trans. 4, (1976), 502; (d) D.B. Harper, Biochem. J. 165, (1977), 309; (c) M. Kobayashi and S. Shimizu, FEMS Microbiol. Lett. 120, (1994), 217.

  3. (a) Y. Asano, Y. Tani and H. Yamada, Agric. Biol. Chem. 44, (1980), 2251; (b) Y. Asano, K. Fujishiro, Y. Tani and H. Yamada, Agric. Biol. Chem. 46, (1982), 1165; (c) Y. Asano, M. Tachibana, Y. Tani and H. Yamada, Agric. Biol. Chun. 46, (1982), 1175.

  4. For useful overviews, see (a) L. Martinkova and V. Kren, Biocatal. Biotrans. 20, (2002), 73; (b) D.A. Cowan, R.A. Cameron and T.L. Tsekoa, Ad v. Appl.Microbiol. 52, (2003), 123.

  5. (a) P.A. Collins and C.J. Knowles, J. Gen. Microbiol. 129, (1983), 711; (b) E.A. Linton and C.J. Knowles, J. Gen. Microbiol. 132, (1986), 1493; (c) P.A. Vaughan, P.S.J. CHeetham and C.J. Knowles, J. Gen. Microbiol. 134, (1988), 1099.

  6. (a) T. Nagasawa, T. Nakamura and H. Yamada, Arch. Microbiol. 155, (1990), 13; (b) T. Nagasawa, K. Takeuchi, V. Nardi-Dei, Y.␣Mikara and H. Yamada, Appl. Microbiol. Biotechnol. 34, (1991), 783; (c) M. Kobayashi, H. Komeda, T. Nagasawa, H.␣Yamada and S. Shimizu, Biosci. Biotechnol. Biochem. 57, (1993), 1949; (d) For a latest review, see H. Yamada, S. Shimizu and M.␣Kobayashi, Chem. Record 1, (2001), 152 and references cited therein.

  7. (a) K. Ryuno, T. Nagasawa and H. Yamada, Agric. Biol. Chem. 52, (1988), 1813; (b) T. Nagasawa, K. Ryuno and H. Yamada, Experientia, 45, (1989), 1066.

  8. (a) A. Arnaud, P. Galzy and J.-C. Jallageas, Agric. Biol. Chem. 41, (1982), 2183; (b) T. Nagasawa, K. Ryuno and H. Yamada, Biochem. Biophy. Res. Commun. 139, (1986), 1305; (c) Y. Sugiura, J. Kuwahara, T. Nagasawa and H. Yamada, J. Am. Chem. Soc. 109, (1987), 5848; (d) J.-F. Mayaux, E. Cerbelaud, F. Soubrier, D. Faucher and D. Petre, J. Bacteriol 172, (1990), 6764.

  9. (a) T. Nnagamune, H. Kurata, M. Hirata, J. Honda, A. Hirata and I. Endo, Photochem. Photobiol. 51, (1990), 1; (b) J. Honda, T.␣Nagamune, Y. Tetrani; A. Hirata, H. Sasabe and I. Endo, NY Acad. Sci. USA, 672, (1992), 29.

  10. (a) I. Watanabe, Y. Satoh and K. Enomoto, Agric. Biol. Chem. 51, (1987), 3193; (b) I. Watanabe, Y. Satoh, K. Enomoto, S. Seki and K. Sakashita, Agric. Biol. Chem. 51, (1987), 3201; (c) T. Endo and I. Watanabe, FEBS Lett. 243, (1989), 61.

  11. M.A. Cohen J. Sawden N.J. Turner (1990) Tetrahedron Lett. 31 7223 Occurrence Handle10.1016/S0040-4039(00)97285-X

    Article  Google Scholar 

  12. H. Kakeya N. Sakai T. Sugai H. Ohta (1991) Tetrahedron Lett. 32 1343 Occurrence Handle10.1016/S0040-4039(00)79663-8

    Article  Google Scholar 

  13. A.J. Blakey J. Colby E. Williams C. O’Reilly (1995) FEMS Microbiol. Lett. 129 57 Occurrence Handle10.1016/0378-1097(95)00135-R

    Article  Google Scholar 

  14. (a) O. Meth-Cohn and M.-X. Wang, Tetrahedron Lett. 36, (1995), 9561; (b) O. Meth-Cohn and M.-X. Wang, J. Chem. Soc., Perkin Trans. 1(1997), 1099.

  15. (a) O. Meth-Cohn and M.-X. Wang, Chem. Commun. (1997), 1041; (b) O. Meth-Cohn and M.-X. Wang, J. Chem. Soc., Perkin Trans. 1(1997), 3197.

  16. W. Huang J. Jia J. Cummings M. Nelson G. Schneider Y. Lindvist (1997) Structure 5 691 Occurrence Handle10.1016/S0969-2126(97)00223-2 Occurrence Handle9195885

    Article  PubMed  Google Scholar 

  17. S. Nagashima M. Nakasako N. Dohmae M. Tsujimura K. Takio M. Odeka M. Yohda N. Kamiya I. Endo (1998) Nat. Struct. Biol. 5 347 Occurrence Handle10.1038/nsb0598-347 Occurrence Handle9586994

    Article  PubMed  Google Scholar 

  18. A. Miyanaga S. Fushinobu K. Ito T. Wakagi (2001) Biochem. Biophy. Res. Commun. 288 1169 Occurrence Handle10.1006/bbrc.2001.5897

    Article  Google Scholar 

  19. M. Makosza and B. Serafin, Rocz. Chem. 39, (1965), 1401, Chem. Abs. 64, (1966), 17474g.

  20. J.-P. Rieu A. Doucherle H. Cousse G. Mouzin (1986) Tetrahedron 42 4095 Occurrence Handle10.1016/S0040-4020(01)87634-1

    Article  Google Scholar 

  21. M.A. Cohen J.S. Parratt N.J. Turner (1992) Tetrahedron: Asymmetry 3 1543 Occurrence Handle10.1016/S0957-4166(00)86056-5

    Article  Google Scholar 

  22. T. Gilligan H. Yamada T. Nagasawa (1993) Appl. Microbiol. Biotechnol. 39 720 Occurrence Handle10.1007/BF00164456 Occurrence Handle7764117

    Article  PubMed  Google Scholar 

  23. M.-X. Wang G. Lu G.-J. Ji Z.-T. Huang O. Meth-Cohn J. Colby (2000) Tetrahedron: Asymmetry 11 1123 Occurrence Handle10.1016/S0957-4166(00)00025-2

    Article  Google Scholar 

  24. Z.-L. Wu Z.-Y. Li (2001) Tetrahedron: Asymmetry 12 3305 Occurrence Handle10.1016/S0957-4166(02)00017-4

    Article  Google Scholar 

  25. (a) L. Martinkova, A. Stolz and H.-J. Knackmuss, Biotechnol. Lett. 18, (1996), 1073; (b) I. Prepechalova, L. Martinkova, A.␣Stolz, M. Ovesna, K. Bezouska, J. Kopecky and V. Kren, Appl.Microbiol. Biotech. 55, (2001), 150.

  26. K. Yamamoto Y. Ueno K. Dtsubo K. Kawakami K.-I. Komatsu (1990) Appl. Environ. Microbiol. 56 3125 Occurrence Handle2285318

    PubMed  Google Scholar 

  27. M. Gragly C. J. Knowles (1994) Biotechnol. Lett. 16 41 Occurrence Handle10.1007/BF01022621

    Article  Google Scholar 

  28. M.-X. Wang J.-J. Li G.-J. Ji J.-S. Li (2001) J. Mol. Galal B-Enzym. 14 77 Occurrence Handle10.1016/S1381-1177(00)00239-3

    Article  Google Scholar 

  29. S.-I. Masutomo A. Inoue K. Kumagai R. Murai S. Mitsuda (1995) Biosci. Biotechnol. Biochem. 59 720

    Google Scholar 

  30. Y. Crameri J. Foricher M. Scalone R. Schmid (1997) Tetrahedron: Asymmetry 8 3617 Occurrence Handle10.1016/S0957-4166(97)00498-9

    Article  Google Scholar 

  31. I. Nakayama, N. Ohno, K. Aketa, Y. Suzuki, T. Kato and H.␣Yoshioka, in: Advances in Pesticide Science, ed. H. Geissbuhler, Part 2 (Pergamon Press, Oxford, UK, 1979), pp. 174–181.

  32. M.-X. Wang S.-M. Zhao (2002) Tetrahedron: Asymmetry 13 1695 Occurrence Handle10.1016/S0957-4166(02)00470-6

    Article  Google Scholar 

  33. M.-X. Wang S.-M. Zhao (2002) Tetrahedron Lett. 43 6617 Occurrence Handle10.1016/S0040-4039(02)01449-1

    Article  Google Scholar 

  34. For a review, see G.M. Coppola and H.F. Schuster, Asymmetric Synthesis, Construction of Chiral Molecules Using Amino Acids, (Wiley, New York, 1987).

  35. For reviews, see (a) R.O. Duthaler, Tetrahedron 50, (1994), 1539; (b) R.M. Williams and J.A. Hendrix, Chem. Rev. 92, (1992), 889; (c) R.M. Williams, Synthesis of Optically Active α -Amino Acids. (Pergamon, Oxford, 1989).

  36. T.C. Bhalla A. Miura A. Wakamoto Y. Ohba Y. Furuhashi (1992) Appl. Microbiol. Biotechnol. 37 184 Occurrence Handle10.1007/BF00178168

    Article  Google Scholar 

  37. A.M. Macdam C.J. Knowles (1985) Biotechnol. Lett. 7 865 Occurrence Handle10.1007/BF01088007

    Article  Google Scholar 

  38. S.Y. Choi Y.M. Goo (1986) Arch. Phar: Res. 9 45

    Google Scholar 

  39. M. A. Wegman U. Heinemann F. Rantuijk ParticleVan A. Stolz R.A. Sheldon (2001) J. Mol. Catal B-Enzym. 11 249 Occurrence Handle10.1016/S1381-1177(00)00089-8

    Article  Google Scholar 

  40. (a) M.-X. Wang and S.-J. Lin, Tetrahedron Lett. 42, (2001), 6925; (b) M.-X. Wang and S.-J. Lin, . Chem. 67, (2002), 6542.

  41. M.-X. Wang S.-J. Lin J. Liu Q.-Y. Zheng (2004) Adv. Synth. Catal. 346 439 Occurrence Handle10.1002/adsc.200303219

    Article  Google Scholar 

  42. For a review, see G. Coppola and H. Schuster, α -Hydroxy Acids in Enantioselective Synthesis, (Wiley-VCH, Weinheim, 1997).

  43. For a review of enzymatic synthesis of α -hydroxy acids, see H.␣Gröger, Adv Synth. Catal. 343, (2004), 547.

    Google Scholar 

  44. K. Yamamoto K. Oishi I. Fujimatsu K.-I. Komatsu (1991) Appl. Environ. Microbiol. 57 3028 Occurrence Handle1660699

    PubMed  Google Scholar 

  45. Y. Hashimoto E. Kobayashi T. Endo M. Nishiyama S. Horinouchi (1996) Biosci. Biotechnol. Biochem. 60 1279 Occurrence Handle8987543

    PubMed  Google Scholar 

  46. G. DeSantis Z. Zhu W.A. Greenberg K. Wong J. Chaplin S.R. Hanson B. Farwell L.W. Nicholson C.L. Rand D.P. Weiner D.E. Robertson M.J. Burk (2002) J. Am. Chem. Soc. 124 9024 Occurrence Handle10.1021/ja0259842 Occurrence Handle12148986

    Article  PubMed  Google Scholar 

  47. N. Layh A. Stolz S. Fröster F. Effenberger H.-J. Knackmuss (1992) Arch. Microbiol. 158 405 Occurrence Handle10.1007/BF00276300

    Article  Google Scholar 

  48. (a) D. Bianchi, A. Bosetti, P. Cesti, G. Franzosi and S. Spezia, Biotechnol. Lett. 13, (1991), 241; (b) D. Bianchi, E. Battistel, P.␣Cesti, P. Golini and R. Tassinari, Appl. Microbiol. Biotechnol. 40, (1993), 53.

  49. F. Effenberger S. O. β wald (2001) Tetrahedron: Asymmetry 12 279 Occurrence Handle10.1016/S0957-4166(01)00034-9

    Article  Google Scholar 

  50. (a) N. Klempier, A. De Raadt, K. Faber and H. Griengl, Tetrahedron Lett, 32, (1991), 341; (b) N. Klempier, A. De Raadt, K. Faber and H. Griengl, J. Chem. Soc., Perkin trans. 1, (1992), 137; (c) L. Martinkova, N. Klempier, M. Preiml, M. Ovesna, M. Kuzma, V. Mylerova and V. Kren, Can. J. Chem. 80, (2002), 724; (d) E.C. Harm, A.E. Sigmund, S.K. Fager, F.B. Cooling, J.E. Gavagan, A.␣Ben-Bassat, S. Chauhan, M.S. Payne, S.M. Hennessey and R.␣DiCosimo, Adv. Synth. Catal., 345, (2003), 775; (e) Z.-L. Wu and Z.-Y. Li, J. Mol. Catal. B-Enzym. 22, (2003), 105; (f) M. Preiml, K.␣Hillmayer and N. Kiempier, Tetrahedron Lett. 44, (2003), 5057.

  51. M. Yokoyama N. Imai T. Sugai H. Ohta (1996) J. Mol. Catal B-Enzym. 1 135 Occurrence Handle10.1016/1381-1177(95)00021-6

    Article  Google Scholar 

  52. M.-X. Wang Y. Wu (2003) Org. Biomol. Chem. 1 535 Occurrence Handle10.1039/b209791e Occurrence Handle12926256

    Article  PubMed  Google Scholar 

  53. S.-M. Zhao M.X. Wang (2002) Chinese J. Chem. 20 1291

    Google Scholar 

  54. S.K. Taylor N.H. Chmiel L.J. Simons J.R. Vyvyan (1996) Chem. 61 9084

    Google Scholar 

  55. M.-X. Wang G.-Q. Feng (2000) Tetrahedron Lett. 41 6501 Occurrence Handle10.1016/S0040-4039(00)01031-5

    Article  Google Scholar 

  56. M.-X. Wang G-Q. Feng (2002) New J. Chem. 26 1575 Occurrence Handle10.1039/b200110a

    Article  Google Scholar 

  57. G.-Q. Feng M.-X. Wang (2001) Chinese J. Chem. 19 113

    Google Scholar 

  58. M.-X. Wang G.-Q. Wang (2002) J. Mol. Catal B-Enzym. 18 267 Occurrence Handle10.1016/S1381-1177(02)00105-4

    Article  Google Scholar 

  59. M.-X. Wang G.-Q. Feng (2003) Chem. 68 622

    Google Scholar 

  60. (a) M.-X. Wang, G.-Q. Feng and Q.-Y. Zheng, Adv. Synth. Catal. 345, (2003), 695; (b) M.-X. Wang, G.-Q. Feng and Q.-Y. Zheng, Tetrahedron; Asymmetry 15, (2004), 347.

  61. M.-X. Wang S.-J. Lin C.-S. Liu Q.0Y. Zheng J.-S. Li (2003) Chem. 68 4570

    Google Scholar 

  62. H. Kakeya, N. Sakai, M. Yokoyama, T. Sugai and H. Ohta, Chem. Lett. (1991), 1823.

  63. T. Beard M.A. Cohen J.S. Parratt N.J. Turner J. Crosby J. Moilliet (1993) Tetrahedron: Asymmetry 4 1085 Occurrence Handle10.1016/S0957-4166(00)80215-3

    Article  Google Scholar 

  64. S.J. Maddrell N.J. Turner A. Kerridge A. Willetts J. Crosby (1996) Tetrahedron Lett. 37 6001 Occurrence Handle10.1016/0040-4039(96)01259-2

    Article  Google Scholar 

  65. M.-X. Wang C.-S. Liu J.-S. Li O. Meth-Cohn (2000) Tetrahedron Lett. 41 8549 Occurrence Handle10.1016/S0040-4039(00)01518-5

    Article  Google Scholar 

  66. M.-X. Wang C.-S. Liu J.-S. Li (2001) Tetrahedron: Asymmetry 12 3367 Occurrence Handle10.1016/S0957-4166(02)00028-9

    Article  Google Scholar 

  67. M. Yokoyama T. Sugai H. Ohta (1993) Tetrahedron: Asymmetry 4 1081 Occurrence Handle10.1016/S0957-4166(00)80214-1

    Article  Google Scholar 

  68. Z.-L. Wu and Z.-Y. Li, Chem. Commun. (2003), 386.

  69. K. Matoishi A. Sano N. Imai T. Yamazaki M. Yokoyama T. Sugaiand H. Ohta (1998) Tetrahedron: Asymmetry 9 1097 Occurrence Handle10.1016/S0957-4166(98)00084-6

    Article  Google Scholar 

  70. J.-J. Li J.-S. Li M.-X. Wang (2001) Acta Chim. Sinica 59 1827

    Google Scholar 

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  1. Laboratory of Chemical Biology, Center for Molecular Science, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100080, China

    Mei-Xiang Wang

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Wang, MX. Enantioselective Biotransformations of Nitriles in Organic Synthesis. Top Catal 35, 117–130 (2005). https://doi.org/10.1007/s11244-005-3817-1

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