12
Views
9
CrossRef citations to date
0
Altmetric
Original Article

Reduction of 2-Substituted Cyclohexanones by Saccharomyces Cerevisiae

, , , &
Pages 233-243 | Received 04 Oct 1995, Accepted 17 Mar 1996, Published online: 11 Jul 2009

References

  • D'Arrigo H. E., Högberg H. E., Pedrocchi-Fantoni G., Servi S. Old and new synthetic capacities of baker's yeast. Biocatalysis 1994; 9: 299–312
  • Bucciarelli M., Forni A., Moretti I., Prati F., Torre G. Substituent effect on the absolute stereochemistry of the asymmetric reduction of fluorine-containing (3-diketones by baker's yeast. Biocalalyis 1994; 9: 313–320
  • Canonne P., Bernatchez M. Highly stereoselective synthesis of trans-1,2-disubstituted cycloalkanols. J. Org. Chem 1987; 52: 4025–4031
  • Dale J. A., Dull D. L., Mosher H. S. α-Methoxy-α-trifluoromethylphenylacetic acid, a versatile reagent for the determination of enantiomeric composition of alcohols and amines. J. Org. Chem 1969; 34: 2543–2549
  • Dale J. A., Mosher H. S. Enantiomeric purity of phenylethylene glycol and reliability of phenylglyoxylate asymmetric reduction in configurational assignment. J. Org. Chem 1970; 35: 4002–4003
  • Dale J. A., Mosher H. S. Nuclear magnetic resonance enantiomer reagent. Configurational correlations via nuclear magnetic resonance chemical shifts of diastereomeric mandelate, O-methylmandelate, and α-methoxy-α-trifluoro-methyl-phenylacetate (MTPA) esters. J. Am. Chem. Soc 1973; 95: 512–519
  • Hunt J. R., Carter A. S., Murrell J. C., Dalton H., Hallinan K. O., Crout D. H. G., Holt R. A., Crosby J. Yeast catalyzed reduction of (β-ketoesters (1): Factors affecting whole-cell catalytic activity and stereoselectivity. Biocatalysis and Biotransformation 1995; 12: 159–178
  • Jones J. B. Enzymes in organic synthesis. Tetrahedron 1986; 42: 3351–3403
  • Minamikawa J., Brossi A. Selective O-demethylation of an aromatic methyl-ester in the presence of an aromatic methylenedioxy group with trimethylsilyl iodide in quinoline. Tetrahedron Lett 1978; 3085–3086
  • Moran P. J. S., Rodrigues J. A. R., Joekes I., Brenelli E. C. S., Leite R. A. Reduction of α-azidopropiohenone by immobilized baker's yeast. Biocatalysis 1994; 9: 321–328
  • Patel R. N., Banerjee A., McNamee C. G., Brozozowski D., Hanson R. L., Szarka L. J. Enantioselective microbial reduction of 3,5-dioxo-6-(benzyloxy)-hexanoic acid, ethyl ester. Enzyme Microb. Technol 1993; 15: 1014–1021
  • Rinaldi P. L. The determination of absolute configuration using nuclear magnetic resonance techniques. Prog. Nucl. Magn. Resort. Spectrosc 1982; 15: 291–351
  • Rejzek M., Wimmer Z., Zarevúcka M., Pavlík M., Ŝaman D., Řícánková M. Chiral juvenoids derived from 2-substituted cyclohexanols. Tetrahedron: Asymm 1994a; 5: 1501–1512
  • Rejzek M., Wimmer Z., Ŝaman D., Říčánková M. Synthesis and structure-activity relationships of juvenoids derived from 2-(4-hydroxybenzyl)-cycloalkan-1-ones. Helvetica Chimica Acta 1994b; 71: 1241–1255
  • Servi S. Baker's yeast as reagent in organic synthesis. Synthesis 1990; 1–25
  • Sih C. H., Chen C. H. Microbial asymmetric catalysis — enantioselective reduction of ketones. Angew. Chem. Int. Ed. Engl 1984; 23: 570–578
  • Sullivan G. R., Dale J. A., Mosher H. S. Correlation of configuration and 19F chemical shifts of α-methoxy-α-trifluoromethylphenylacetate derivatives. J. Org. Chem 1973; 38: 2143–2147
  • Van Middlesworth F., Sih C. J. A model for predicting diastereoselectivity in yeast reductions. Biocatalysis 1987; 1: 117–127
  • Vogel A. I. Physical properties and chemical constitution. Part XXIII. Miscellaneous compounds. Investigation of the so-called coordinate or dative link in esters of oxy-acids and in nitro-paraffins by molecular refractivity determinations. Atomic, structural, and group parachors and refractivities. J. Chem. Soc 1948; 1833–1855
  • Ward O. P., Young C. S. Reductive biotransformation of organic compounds by cells or enzymes of yeast. Enzyme Microb. Technol 1990; 12: 482–493
  • Wimmer Z., Streinz L., Romanˆuk M. Preparation of carbamate derivatives of 2-(4-hydroxybenzyl)-1-cyclohexanone with a juvenoid activity. Collect. Czech. Chem. Commun 1985; 50: 2543–2456
  • Wimmer Z., Buděšínský M., Macek T., Svatoš A., Ŝaman D., Vašičková S., Romanˆuk M. Biotransformation of 2-(4-methoxybenzyl)-1-cyclo-hexanone by means of Saccharomyces cerevisiae. Collect. Czech. Chem. Commun 1987; 52: 2326–2337
  • Wimmer Z., Vanêk T., Macek, Ŝaman D., Svatoš A. Reduction of 2-substituted cyclohexanones by Saccharomyces cerevisiae under aerobic and anaerobic conditions. Enzyme Microb. Technol 1992; 14: 197–202
  • Zarevucka M., Rejzek M., Wimmer Z., Ŝaman D., Streinz L. Chiral precursors of optically active juvenoids. Tetrahedron 1993; 49: 5305–5314
  • Zhou B., Gopalan A. S., Van Middlesworth F., Sheih W. R., Sih C. J. Stereochemical control of yeast reductions. I. Asymmetric synthesis of L-carnitine. J. Am. Chem. Soc 1983; 105: 5925–5926

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.