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Asymmetric bioreduction of keto esters by immobilized baker's yeast entrapped in calcium alginate beads in both water and organic/water solvent systems

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Abstract

Immobilized baker's yeast entrapped in calcium alginate beads, ca 1.5 mm diameter, was used more than 10 times in water and reduced ethyl 3-oxobutanoate and ethyl benzoylformate to the corresponding chiral hydroxy esters in good chemical yields and in high enantioselectivities. The biocatalyst was also successfully used in organic/water solvent systems such as hexane/water and acetonitrile/water, and in other systems, particularly in hexane, converted keto esters into their individual chiral hydroxy esters.

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References

  • Davies, H.G., Green, R.H., Kelly, D.R. & Roberts, S.M. 1989 Biotransformations in Preparative Organic Chemistry. The Use of Isolated Enzymes and Whole Cell Systems in Symthesis. New York: Academic Press.

    Google Scholar 

  • Gramatica, P. 1988 Biotransformations in organic synthesis. Baker's yeast-mediated reductions. Chimica Oggi 17–20.

  • Mori, K. 1989 Synthesis of optically active pheromones. Tetrahedron 45, 3233–3298.

    Google Scholar 

  • Mosbach, K. 1985 Immobilized enzymes in organic synthesis. In Enzymes in Organic Synthesis, eds Porter, R. & Clark, S. pp. 57–70. London: Pitman Press.

    Google Scholar 

  • Nakamura, K., Inoue, K., Ushio, K., Oka, S. & Ohno, A. 1988 Stereochemical control on yeast reduction of α-keto esters. Reduction by immobilized bakers' yeast in hexane. Journal of Organic Chemistry 53, 2589–2593.

    Google Scholar 

  • Naoshima, Y. & Hasegawa, H. 1987 Synthesis of both enantiomers of phoracantholide I, a defensive secretion of the eucarypt longicorn, employing asymmetric reduction with immobilized baker's yeast. Chemical Letters 2379–2382.

  • Naoshima, Y., Hasegawa, H. & Saeki, T. 1987 Synthesis of (R)-enantiomers of 5-hexadecanolide and 4-dodecanolide, pheromone of the oriental hornet and a defensive secretion of rove beetles, employing asymmetric reduction with immobilized baker's yeast. Agricultural and Biological Chemistry 51, 3417–3419.

    Google Scholar 

  • Naoshima, Y., Hasegawa, H., Nishiyama, T. & Nakamura, A. 1989a Synthesis of both the enantiomers of phoracantholide I, a defensive secretion of the eucarypt longicorn (Phoracantha synonyma), employing microbial asymmetric reduction with immobilized baker's yeast. Bulletin of the Chemical Society of Japan 62, 608–610.

    Google Scholar 

  • Naoshima, Y., Nakamura, A., Nishiyama, T., Haramaki, T., Mende, M. & Munakata, Y. 1989b Asymmetric bioreduction of ethyl 3-oxobutanoate by immobilized baker's yeast entrapped in calcium alginate beads. Application of the immobilized biocatalyst to the synthesis of (5Z,13S)-5-tetradecen-13-olide, aggregation pheromone of Cryptolestes grain beetle. Chemical Letters 1023–1026.

  • Naoshima, Y., Nishiyama, T. & Munakata, Y. 1989c Bioreduction of ethyl 3-oxobutanoate with immobilized baker's yeast in organic-water solvent systems. Chemical Letters 1517–1518.

  • Naoshima, Y., Nakamura, A., Munakata, Y., Kamezawa, M. & Tachibana, H. 1990a Synthesis of (5Z,13S)-5-tetradecen-13-olide, aggregation pheromone of Cryptolestes grain beetle, employing asymmetric bioreduction with immobilized bakers' yeast entrapped in calcium alginate beads. Bulletin of the Chemical Society of Japan 63, 1263–1265.

    Google Scholar 

  • Naoshima, Y., Maeda, J., Munakata, Y., Nishiyama, T., Kamezawa, M. & Tachibana, H. 1990b Bioreduction with immobilized bakers' yeast in hexane using alcohols as an energy source. Journal of the Chemical Society, Chemical Communications 964–965.

  • Seebach, D., Sutter, M.A., Weber, R.H. & Zuger, M.F. 1985 Yeast reduction of ethyl acetoacetate: (S)-(+)-ethyl 3-hydroxybutanoate. In Organic Synthesis, Vol. 63, ed. Saucy, G. pp. 1–9. New York: John Wiley.

    Google Scholar 

  • Shieh, W.R., Gopalan, A.S. & Sih, C.J. 1985 Stereochemical control of yeast reductions. 5. Characterization of the oxido-reductases involved in the reduction of β-keto esters. Journal of the American Chemical Society 107, 2993–2994.

    Google Scholar 

  • Turner, N.J. 1989 Recent advances in the use of enzyme-catalysed reactions in organic synthesis. Natural Products Report 6, 625–644.

    Google Scholar 

  • Whitaker, J.R. & Sonnet, P.E. (eds) 1989 Biocatalysis in Agricultural Biotechnology. ACS Symposium Series 389. Washington, DC: American Chemical Society.

    Google Scholar 

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Naoshima, Y., Munakata, Y., Nishiyama, T. et al. Asymmetric bioreduction of keto esters by immobilized baker's yeast entrapped in calcium alginate beads in both water and organic/water solvent systems. World Journal of Microbiology and Biotechnology 7, 219–224 (1991). https://doi.org/10.1007/BF00328993

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  • DOI: https://doi.org/10.1007/BF00328993

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