Saccharomyces cerevisiae reduction

Alternative Step D Reduction with a Reductate — Sucrose (1 kg) is dissolved in water (9 liters) in a 20-liter bottle equipped with a gas trap. Baker s yeast Saccharomyces cerevisiae, 1 kg) is made into a paste with water (1 liter) and added to the sucrose solution with stirring. After lively evolution of gas begins (within 1 to 3 hours), 3-morpholino-4-(3-tert-butylamino-2-oxopropoxy)-1,2,5-thiadiazole hydrogen maleate [1.35 mols, prepared by reaction of the 3-morpholino-4-(3-tert-butylamino-2-oxopropoxy)-1,2,5-thiadiazole with an equimolar quantity of maleic acid in tetrahydrofuran]. The mixture is allowed to stand until fermentation subsides, after which the bottle is kept in a 32°C incubator until all fermentation has ended (in approximately 1 to 3 days). The yeast is filtered off with addition of diatomaceous earth and the filtrate is evaporated to dryness to give S-3-mor-pholino-4/3-tert-butylamino-2-hydroxypropoxy)-1,2,5-thiadiazole, MP 195° to 198°C (as hydrogen maleate), according to U.S. Patent 3,619,370. 

In the reduction of racemic /i-ketosulphoxides (e.g. 464a) with actively fermenting yeast (Saccharomyces cerevisiae) the enantiomers are reduced at sufficiently different rates to allow isolation of optically active /1-hydroxy sulphoxide 524 and unreacted optically active /1-ketosulphoxide with at least 95% optical purity617,618 (equation 323). 

A molecular variation of plasma membrane has been reported by Puccia et al. Reduction of total lipids (XL) content and significant variations of triglyceride (TG) and phospholipids (PL) fractions were observed as a consequence of exposure of C. intestinalis ovaries to TBTCl solutions. In particular, an evident TG decrease and a PL increase were observed, which probably provoked an increment in membrane fluidity, because of the high concentration of long chain fatty acids and, as a consequence, PL. This could be a cell-adaptive standing mechanism toward the pollutants, as observed in Saccharomyces cerevisiae. Also the increase in the content of the polyunsaturated fatty acids (PUPA), important in the synthesis of compounds such as prostaglandin which are present in the ovary in a stress situation, was probably a consequence of a defense mechanism to the stress provoked by the presence of TBTCl. 

An unusual reaction was been observed in the reaction of old yellow enzyme with a,(3-unsat-urated ketones. A dismutation took place under aerobic or anaerobic conditions, with the formation from cyclohex-l-keto-2-ene of the corresponding phenol and cyclohexanone, and an analogous reaction from representative cyclodec-3-keto-4-enes—putatively by hydride-ion transfer (Vaz et al. 1995). Reduction of the double bond in a,p-unsaturated ketones has been observed, and the enone reductases from Saccharomyces cerevisiae have been purified and characterized. They are able to carry out reduction of the C=C bonds in aliphatic aldehydes and ketones, and ring double bonds in cyclohexenones (Wanner and Tressel 1998). Reductions of steroid l,4-diene-3-ones can be mediated by the related old yellow enzyme and pentaerythritol tetranitrate reductase, for example, androsta-A -3,17-dione to androsta-A -3,17-dione (Vaz etal. 1995) and prednisone to pregna-A -17a, 20-diol-3,ll,20-trione (Barna et al. 2001) respectively. 

The enantiomeric reduction of 2-nitro-l-phenylprop-l-ene has been studied in a range of Gram-positive organisms including strains of Rhodococcus rhodochrous (Sakai et al. 1985). The enantiomeric purity of the product depended on the strain used, the length of cultivation, and the maintenance of a low pH that is consistent with the later results of Meah and Massey (2000). It has been shown that an NADPH-linked reduction of a,p-unsaturated nitro compounds may also be accomplished by old yellow enzyme via the flcf-nitro form (Meah and Massey 2000). This is formally analogous to the reduction and dismutation of cyclic enones by the same enzyme (Vaz et al. 1995), and the reductive fission of nitrate esters by an enzyme homologous to the old yellow enzyme from Saccharomyces cerevisiae (Snape et al. 1997). 

Kaluzna, I.A., Matsuda, T., Sewell, A.K. and Stewart, J.D. (2004) Systematic investigation of Saccharomyces cerevisiae enzymes catalyzing carbonyl reductions. Journal of the American Chemical Society, 126 (40), 12827-12832. 

Padhi, S.K., Kaluzna, I.A., Buisson, D. et al. (2007) Reductions of cyclic beta-keto esters by individual Saccharomyces cerevisiae dehydrogenases and a chemo-enzymatic route to (lR,2S)-2-methyl-l-cyclohexanol. Tetrahedron Asymmetry, 18 (18), 2133-2138. 

Yang, Y., Zhu, D., Piegat, T.J. and Hua, L. (2007) Enzymatic ketone reduction mapping the substrate profile of a short-chain alcohol dehydrogenase (YMR226c) from Saccharomyces cerevisiae. Tetrahedron Asymmetry, 18 (15), 1799-1803. 

Engelking, H., Pfaller, R., Wich, G. and Weuster-Botz, D. (2006) Reaction engineering studies on /3-ketoester reductions with whole cells of recombinant Saccharomyces cerevisiae. Enzyme and Microbial Technology, 38, 536-544. 

Figure 14.9 Reaction scheme for production of (—)-ephedrine based on enzymatic C—C bond formation using Saccharomyces cerevisiae coupled with a chemical reductive animation...

Several catalysts are used in the field of microbial reductions. The common features of these catalysts are the high selectivity and their use only on a laboratorial scale. They are applied, for example, in the stereoselective synthesis of pharmaceutical intermediates. The reductions are exclusively selective either in the hydrogenation of the C=C double bond or in that of other reducible groups. One of the most widely used catalysts is baker s yeast. In the following hydrogenations, which are catalyzed by Saccharomyces cerevisiae, high enantioselectivities were achieved (equations 35-38)105-108. 

The reduction of Woodward s lactone with Saccharomyces cerevisiae produced an intermediate which is used for the preparation of hypotensive alkaloids (equation 44)118. 

Bisconti L, Pepi M, Mangani S, Baldi F. 1997. Reduction of vanadate to vanadyl by a strain of Saccharomyces cerevisiae. Biometals 10 239-46. 

Cytochrom c Peroxidase [13] Saccharomyces cerevisiae 2Cc(II) + H2O2 2Cc(III) + 2H2O Reduction of H2O2 and oxidation of Cytochrom c... 

Metal amalgams may be used for reduction of the keto groups in keto esters provided the medium does not cause hydrolysis of the ester. Because of that aluminum amalgam in ether is preferable to sodium amalgam in aqueous solutions. Diethyl oxalacetate was reduced to diethyl malate by sodium amalgam in 50% yield and with aluminum amalgam in 80% yield [148], Stereospecific reduction of a- and fi-keto esters to optically pure hydroxy esters was achieved by biochemical reduction in moderate to good yields. Saccharomyces cerevisiae converted methyl 2-keto-2-phenylacetate to methyl... 

Saccharomyces cerevisiae (Baker Yeast) are micro organisms and are used for the reduction of carbonyl group to hydroxyl group and for reduction of double bond. 

Stansfield 1, Jones KM, Kushnirov VV, Dagkesamanskaya AR, Poznyakovski Al, Paushkin SV, Nierras CR, Cox BS, Ter-Avanesyan MD, Tuite ME (1995) The products of the SUP45 (eRFl) and SUP35 genes interact to mediate translation termination in Saccharomyces cerevisiae. EMBO J 14 4365 373 Stansfield 1, Eurwilaichitr L, Akhmaloka, Tuite ME (1996) Depletion in the levels of the release factor eRFl causes a reduction in the efficiency of translation termination in yeast. Mol Microbiol 20 1135-1143 Stansfield 1, Kushnirov VV, Jones KM, Tuite ME (1997) A conditional-lethal translation termination defect in a sup45 mutant of the yeast Saccharomyces cerevisiae. Fur J Biochem 245 557-563 Stark H (2002) Three-dimensional electron cryomicroscopy of ribosomes. Curr Protein Pept Sci 3 79-91... 

Recently, it has been demonstrated that the yeast Saccharomyces cerevisiae (DHW S-3) can also be used for the (R)-selective reduction of the acetylsilane rac-48. By analogy with the bioconversions illustrated in Scheme 10, incubation of rac-48 with resting free cells of this microorganism yielded a 1 1 mixture of the corresponding diastereomeric (1-hydroxyethyl)silanes (SiR,CR)-49 and (SiS,CR)-5057. Under preparative conditions, the biotransformation products were isolated in 43% yield (relative to rac-48). The enantiomeric purities of the silanes (SiR,CR)-49 and (SiS,CR)-50 were >98% ee. 

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