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Chiral Synthons by New Oxidoreductases and Methodologies

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Biocatalysis

Part of the book series: Van Nostrand Reinhold Catalysis Series ((NRECSES))

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Abstract

For decades it has been known that the preparation of certain chiral compounds can be accomplished with oxidoreductases. The overwhelming majority of reactions that have been carried out involve the reduction of keto groups to chiral secondary alcohols or derivatives thereof. Many substrates can be reduced by alcohol dehydrogenase from liver or microbial sources, and for the former and some others it can be predicted which compound may be a substrate and which stereochemical course may be expected. Also the stereoselective dehy-drogenation of prochiral dialcohols is a valuable approach to many chiral compounds. Many groups contributed to the use of dehydrogenases or microorganisms containing such enzymes and a system for the regeneration of the pyridine nucleotides. Only a few can be mentioned here, with recent articles cited from which their earlier work can be followed. Jones et al. mainly worked with horse liver alcohol dehydrogenase and Sih et al. with yeasts (Dodds and Jones 1988; Van-middlesworth and Sih 1987). Wong and Whitesides worked out important kinetic and technical aspects of coenzyme regeneration on a preparative scale for many systems (Chenault, Simon, and Whitesides 1988).

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References

  • Bader, J., H. Günther, S. Nagata, H. J. Schütz, M. L. Link, and H. Simon. 1984. Unconventional and effective methods for the regeneration of NAD(P)H in microorganisms or crude extracts of cells. J. Biotechn. 1: 95–109.

    Article  CAS  Google Scholar 

  • Balahura, R. J., and R. G. Wilkins. 1983. Ligational effects on reduction of myoglobin and horseradish peroxidase by inorganic reagents. Biochim. Biophys. Acta 724: 465–472.

    Article  CAS  Google Scholar 

  • Chenault, H. K., E. S. Simon, and G. M. Whitesides. 1988. Cofactor regeneration for enzyme-catalysed synthesis. Biotechnol. Genet. Engineer. Rev. 6: 221–270.

    CAS  Google Scholar 

  • Dodds, D. R., and B. J. Jones. 1988. Enzymes in organic synthesis. 38. Preparations of enantiomerically pure chiral hydroxydecalones via stereospecific horse liver alcohol dehydrogenase catalyzed reductions of decalindiones.J. Am. Chem. Soc. 110: 577–583.

    Article  CAS  Google Scholar 

  • Fraisse, L., and H. Simon. 1988. Observations on the reduction of nonactiva-ted carboxylates by Clostridium formicoaceticum with carbon monoxide or formate and the influence of various viologens. Arch. Microbiol. 150: 381–386.

    Article  CAS  Google Scholar 

  • Görgen, G., W. Boland, U. Preiss, and H. Simon. 1989. Synthesis of chiral 12-phenyl(2H)dodecanic acids: Useful metabolic probes for the biosynthesis of 1-alkenes from fatty acids. Helv. Chim. Acta 72: 917–928.

    Article  Google Scholar 

  • Günther, H., S. Neumann, and H. Simon. 1987. 2-Oxocarboxylate reductase from Proteus species and its use in the preparation of (2R)-hydroxy acids. J. Biotechnol. 5: 53–65.

    Google Scholar 

  • Hummel, W., H. Schütte, E. Schmidt, C. Wandrey, and M.-R. Kula. 1987. Isolation of L-phenylalanine dehydrogenase from Rhodococcus sp. M4 and its application for the production of L-phenylalanine. Appl. Microbiol. Biotechnol. 26: 409–416.

    Article  CAS  Google Scholar 

  • Kim, M. J., and G. M. Whitesides. 1988. L-Lactate dehydrogenase: substrate specificity and use as a catalyst in the synthesis of homochiral 2-hydroxy acids.J. Am. Chem. Soc. 110: 2959–2964.

    Article  CAS  Google Scholar 

  • Klier, K., G. Kresse, O. Werbitzky, and H. Simon. 1987. The microbial splitting of the N-O bond of dihydrooxazines; an alternative to the chemical reduction. Tetrahedron Lett. 28: 2677–2680.

    Article  CAS  Google Scholar 

  • Kuno, S., A. Bacher, and H. Simon. 1985. Structure of enoate reductase from a Clostridium tyrobutyricum (C. spec. La1). Hoppe Seyler Z. Biol. Chem. 366: 463–472.

    Article  CAS  Google Scholar 

  • Nagata, S., R. Feicht, W. Bette, H. Günther, and H. Simon. 1987. On a viologen-dependent pyridine nucleotide oxidoreductase from a thermophilic Bacillus. Appl. Microbiol. Biotechnol. 26: 263–267.

    Article  CAS  Google Scholar 

  • Preiss, U., H. White, and H. Simon. 1989. Additional enoates and other α, β-unsaturated carbonyl compounds as substrates for the enoate reductase from Clostridium tyrobutyricum, influence of elevated hydrogen pressure on the reduction rate. Dechema Biotechnology Conferences, Vol. 3 (D. Behrens ed.), pp. 189–192. Weinheim: Verlag Chemie.

    Google Scholar 

  • Schummer, A., H. Yu, C. Schinschel, P. Rauschenbach, and H. Simon. 1989. Preparation of multifunctional (2R)- or (2S)-hydroxy acids by Proteus vulgaris and their conversion to compounds with two or three chiral centers. Dechema Biotechnology Conferences Vol. 3 (D. Behrens, ed.), pp. 271–274. Weinheim: Verlag Chemie.

    Google Scholar 

  • Sih, C. J. and C.-S. Chen. 1984. Microbial asymmetric catalysis—enantiose-lective reductions of ketones. Angew. Chem. Int. Ed. Engl. 23: 570–578.

    Article  Google Scholar 

  • Simon, H. 19xx. In Chemistry and Biochemistry of Flavoenzymes, Vol. III (F. Mueller, ed.). CRC Press, Boca Raton, FL, in press.

    Google Scholar 

  • Simon, H., J. Bader, H. Günther, S. Neumann, and J. Thanos. 1985. Chiral compounds synthesized by biocatalytic reductions. Angew. Chem. Int. Ed. Engl. 24: 539–553.

    Article  Google Scholar 

  • Simon, H., H. White, H. Lebertz, and I. Thanos. 1987. Reduktion von 2-Enoaten und Acylaten mit Kohlenmonoxid oder Formiat, Viologenen und Clostridium thermoaceticum zu gesättigten Säuren und ungesättigten bzw, gesättigten Alkoholen. Angew. Chem. 100: 785–786.

    Article  Google Scholar 

  • Simon, H., and H. Günther. 1988. Microbial and enzymic production of labeled compounds. In Biotechnology, Vol. 6b. (H.-J. Rehm, and G. Reed, eds.), pp. 171–192. Weinheim: Verlag Chemie.

    Google Scholar 

  • Skopan, H., H. Günther, and H. Simon. 1987. A biocatalyst for the preparation of (R) and (S)-hydroxylic acids. Angew. Chem. Int. Ed. Engl. 26: 128 – 130.

    Article  Google Scholar 

  • Thanos, J., and H. Simon. 1986. Stereospecific reductions with hydrogen gas, modified metal catalysts, methylviologen and enzymes or microorganisms. Angew. Chem. Int. Ed. Engl. 25: 462–463.

    Article  Google Scholar 

  • Thanos, I., J. Bader, H. Günther, S. Neumann, F. Krauss, and H. Simon. 1987. Electroenzymatic and electromicrobial reductions for preparation of chiral compounds. Methods Enzymol. 136: 302–317.

    Article  CAS  Google Scholar 

  • Thanos, I., and H. Simon. 1987. Electro-enzymic viologen-mediated stereo-specific reduction of 2-enoates with free and immobilized enoate reductase on cellulose filters or modified carbon electrodes.J. Biotechnol. 6: 13–29.

    Article  CAS  Google Scholar 

  • Thanos, I., A. Deffner, and H. Simon. 1988. Further reactions catalysed by enoate reductase; reductions of 2-enals. Dehydrogenation of saturated aldehydes and their racemisation. Biol. Chem. Hoppe-Seyler 369: 263–267.

    Article  Google Scholar 

  • Vanmiddlesworth, F., and C. J. Sih. 1987. A model for predicting diastereose-lectivity in yeast reductions. Biocatalysis 1: 117–127.

    Article  CAS  Google Scholar 

  • White, H., G. Strobl, R. Feicht, and H. Simon. 1989. Carboxylic acid reductase. A new tungsten enzyme catalyses the reduction of nonactivated carboxylic acids to aldehydes. Eur. J. BioChem. 184: 89–96.

    Article  CAS  Google Scholar 

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© 1990 Van Nostrand Reinhold

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Simon, H. (1990). Chiral Synthons by New Oxidoreductases and Methodologies. In: Abramowicz, D.A. (eds) Biocatalysis. Van Nostrand Reinhold Catalysis Series. Springer, Dordrecht. https://doi.org/10.1007/978-94-010-9124-4_11

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  • DOI: https://doi.org/10.1007/978-94-010-9124-4_11

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-94-010-9126-8

  • Online ISBN: 978-94-010-9124-4

  • eBook Packages: Springer Book Archive

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