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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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.
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.
Mosbach, K. 1985 Immobilized enzymes in organic synthesis. In Enzymes in Organic Synthesis, eds Porter, R. & Clark, S. pp. 57–70. London: Pitman Press.
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.
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.
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.
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.
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.
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.
Turner, N.J. 1989 Recent advances in the use of enzyme-catalysed reactions in organic synthesis. Natural Products Report 6, 625–644.
Whitaker, J.R. & Sonnet, P.E. (eds) 1989 Biocatalysis in Agricultural Biotechnology. ACS Symposium Series 389. Washington, DC: American Chemical Society.
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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