23
Views
23
CrossRef citations to date
0
Altmetric
Original Article

Old and New Synthetic Capacities of baker's Yeast

, , &
Pages 299-312 | Published online: 11 Jul 2009

References

  • Azerad R., Buisson D. Stereocontrolled reduction of β-ketoesters with Geotrichum candidum. Microbial Reagents in Organic Synthesis, S. Servi. Academic Publishers, Kluwer. 1992; 121–440, and reference therein
  • Akamanchi K. G., Meenakshi R., Ranbhan K. J. A novel ability of bakers ' yeast in hydrolysis of Amadori compounds (1-deoxy-1-amino-2-ketoses). Indian J. Chem. 1992; 31B: 33–34
  • Brown R. T., Dauda B., Santos E. N, Cid A. M. Hydrolysis and selective reduction with yeast: enantiospecific synthesis of antirhine from secologanin. J. Chem. Soc, Chem. Commun 1991; 825–826
  • Buist P. H., Marecak D. M., Partington E. T., Skala P. Enantioselective sulfoxidation of a fatty acid analogue by bakers yeast. J. Org. Chem.; 1990; 55: 5667–5669
  • Chibata I., Tosa T., Takata I. Continuous production of l-malic acid by immobilised Dells. Trends Biotechnol. 1983; 1: 9–11
  • Chibata I., Tosa T., Sato T. Continuous production of L-aspartic acid. Improvement of productivity by both development of immobilization method and construction of new E. coli strain. Appl. Biochem. Biotechnol. 1986; 13: 231–240
  • Csuk R., Glanzer B. I. Bakers Yeast Mediated Transformations in Organic Chemistry. Chem. Rev. 1991; 91: 49–97
  • D'Arrigo P., Piergianni V, Scarcelli D., Servi S. unpublished results 1993
  • Dillon M. P., Hayes M. A., Simpson T. J., Sweeney J. B. The synthesis of isotopically labeled N-acetylcysteamine thio esters utilizing a baker 's yeast reduction in deuterium oxide. Bioorg. Med. Chem. Lett; 1991; 1: 223–226
  • Faber K. Biotransformations in organic chemistry. Springer Verlag, Berlin 1992
  • Fadnavis N. W., Deshpande A., Chauhan S., Bhalerao U. T. Peptide synthesis mediated by immobilized and viable baker 's yeast in reverse micelles: synthesis of leucine enkephalin analogs. J. Chem. Soc, Chem. Commun. 1990; 1548–1550
  • Fantin G., Fogagnolo M., Medici A., Pedrini P., Poli S., Sinigaglia M. Kinetic Resolution of 1-Arylethanols and 1-Heteroaryl Ethanols by Oxidation with Bakers Yeast. Tetrahedron Lett. 1993; 34: 883–886
  • Fronza G., Fuganti C, Grasselli P., Poli G., Servi S. On the products obtained from γ-oxygen substituted crotonaldehyde in fermenting baker's yeast. Biocatalysis 1990; 3: 51–56
  • Fronza G., Fuganti C, Mele A., Pedrocchi-Fantoni G., Servi S. On the origin of the C3 framework of yeast-generated (R)-S-benzylthioglycerate. J. Org. Chem. 1992a; 57: 999–1002
  • Fronza G., Fuganti C, Grasselli P., Pedrocchi-Fantoni G., Servi S. Minor synthetic capacities of baker's yeast towards unnatural substrates. Pure Appl. Chem. 1992b; 64: 1099–1101
  • Fronza G., Fuganti C, Mele A., Pedrocchi-Fantoni G., Servi S. On the mechanism of baker's yeast mediated synthesis of (R)-S-benzyl thioglycerate. experiments in deuterated water. Tetrahedron 1993, in the press
  • Fuganti C, Grasselli P., Seneci P. F., Casati P. Further information on the steric course of the baker's yeast reduction of 4-substituted-3-oxo butanoates. Tetrahedron Lett. 1986; 27: 5275–5276
  • Fuganti C, Grasselli P., Servi S., Högberg H. E. Baker's yeast mediated preparation of (S)-3-(2-furyl)-2-melhylpropan-l-ol, a bifunctional chiral C5 isoprenoid synthon: synthesis of (4R,8R)-4,8-dimethyldecanal, a pheromone of Tribolium castaneum. J. Chem. Soc. Perkin Trans. 1988; I: 3061–3065
  • Fuganti C, Pedrocchi-Fantoni G., Servi S. (S)-2-methyl-3-phenypropanethiol hemisuccinate: a new chiral material with partial kinetic resolution from baker 's yeast incubation of racemic 2-methyl-3-phenylpropanethiol. Agric. Biol. Chem. 1991; 55: 643–644
  • Glänzer B. I., Faber K., Griengl H. Enantioselective hydrolysis by baker's yeast. III Microbial resolution of alkynyl esters using lyophilised yeast. Tetrahedron 1987; 43: 5791–5796
  • Halgas J. Biocatalysts in organic synthesis. Elsevier, Amsterdam 1992
  • Heidlas J., Engel K.-H., Tressl R. Purification and characterization of two oxidoreductases involved in the enantioselective reduction of 3-oxo, 4-oxo and 5-oxo esters in baker's yeast. Eur. J. Biochem. 1988; 172: 633–639
  • Högberg H. E., Hedenström E., Fägerhag J., Servi S. Enantioselective synthesis of (S)-2-methyl-l-alkanols via bakers yeast mediated reduction of α-methyl-2-thiophenepropenals. J. Org. Chem. 1992; 57: 2052–2059
  • Hoshino T., Williams H. J., Chung Y. S., Scott A. I. Partial purification and characterization of oxidosqualene-lanosterolcyclase from baker's yeast. Tetrahedron 1991; 47: 5925–5932
  • Hudlicky T., Gillman G., Andersen C. Homochiral amine synthesis by Bakers ' yeast resolution of a β-keto amide: 1-phenylethylamine. Tetrahedron: Asymmetry 1992; 3: 281–286
  • Hudlicky T., Tsunoda T., Gadainaselti K. G., Murry I., Keck G. E. Yeast-mediated resolution of β-keto esters of prochiral alcohols. J. Org, Chem. 1991; 56: 3619–3623
  • Kamal A., Rao M. V., Rao A. B. Efficient enzymatic cyclization of 2-(carbamoyloxy)-benzonitrile and 2-(sulfamoyloxy)-benzonitrile by ultrasonically stimulated bakers yeast. Heterocycles 1990a; 31: 577–579
  • Kamal A., Rao M. V., Rao A. B. Enzymatic oxidative conversion of thio to oxo by bakers yeast in thiocarbamates and thioureas. Chem. Lett. 1990b; 655–656
  • Kamal A., Rao M. V., Rao A. B. Enzymatic cyclizations mediated by ultrasonically stimulated baker's yeast - synthesis of imidazo-fused heterocycles. J. Chem. Soc. Perkin Trans. I 1990c; 2755–2757
  • Kamal A., Rao M. V., Meshram H. M. Efficient enzymatic hydrazone hydrolysis by baker's yeast. Tetrahedron Lett. 1991a; 32: 2657–2658
  • Kamal A., Rao M. V., Meshram H. M. Enzymatic deoximation of oximes by ultrasonically stimulated baker yeast. J. Chem. Soc, Perkin Trans. I 1991b; 2056–2057
  • Kyler K. S., Novak M. J. Cyclase mediated synthesis of terpenoids. in S. Servi Ed. Microbial reagents in organic synthesis. Academic Publ., Kluwer. 1992; 3–24
  • Neuberg C. Biochemical reduction at the expenses of sugars. Adv. Carbohydr. Chem. 1949; 4: 75–106
  • Nakamura K., Kawai Y., Nakajima N., Ohno A. A method for controlling the enantioselectivity of reduction with baker's yeast. J. Org. Chem. 1991; 56: 4778–4783
  • Nakamura K. Stereochemical control in microbial reduction in Servi, S. Ed. Microbial eagents in Organic Synthesis. Academic Publishers, Kluwer. 1992; 389–398
  • Nakamura K., Kondo S., I., Kawai Y., Ohno A. Asymmetric reduction of etopantolactone with baker's yeast. Tetrahedron: Asymmetry 1993; 4: 1253–1254
  • Pedrocchi-Fantoni G., Redaelli S., Servi S., Högberg H. E. Chiral amino alcohols om baker's yeast reduction of α-keto-acid derivatives. Gazz. Chim. It. 1992; 122: 499–502
  • Poppe L., Novak L. Selective Biocatalysis - A synthetic approach. VCH, Weinheim 1992
  • Pradines A., Klaébeé A., Périé F., Paul F., Monsan P. Enzymatic synthesis of losphoric monoesters with alkaline phosphatase in reverse hydrolysis conditions. Tetrahedron 1986; 44: 73–6386
  • Rama Rao K., Bhanumathi N., Sattur P. B. Baker 's yeast catalyzed asymmetric cloaddition of nitrile oxides to the C:C bond: improved chiral recognition by using β-cyclodextrin. rahedron Lett. 1990; 31: 3201–3204
  • Rama Rao K., Nageswar Y. V.D., Kumar H. M.S. Biocatalytic Asymmetric Synthesis β-Aminoacid Esters - Improved Chiral Recognition in the Presence of β-Cyclodextrin. etrahedron Letters 1991; 32: 6611–6612
  • Rama Rao K., Kumar H. M.S. Baker's yeast catalysed oxidative coupling of thiols to sulfides. Bioorganic & Medicinal Chem Lett. 1991; 1: 507–508
  • Santaniello E., Ferraboschi P., Grisenti P., Aragozzini F., Maconi E. A biocatalytic iproach to the enantioselective synthesis of (R)- and (S)-malic acid. J. Chem. Soc, Perkin Trans. I 1991; 1–5
  • Santaniello E., Ferraboschi P., Grisenti P., Manzocchi A. The biocatalytic approach the preparation of enantiomerically pure chiral building blocks. Chem. Rev. 1992; 92: 1071–1140
  • Scollar M. P., Sigal G., Klibanov A. M. Preparative resolution of D,L-threonine talysed by immobilised phosphatase. Biotech. Bioeng. 1985; 27: 247–252
  • Seebach D., Sutter M. A., Weber R. H., Züger M. F. Yeast reduction of ethyl etoacetate: (S>-(+)-ethyl-3-hydroxybutanoale. Org. Synth. 1984; 63: 1–9
  • Servi S. Baker's yeast as reagent in organic synthesis. Synthesis 1990; 1–25
  • Microbial Reagents in Organic Synthesis, S. Servi. Kluwer Academic Publishers. 1992, Shieh, W.-R.; Gopalan, A.S. and Sih, C.J. (1985) Stereochemical control of yeast reductions. 6. iastereoselectivity of 2-alkyl-3-oxobutanoate oxido reductases. J. Am. Chem. Soc, 107, 2993–2997
  • Shieh W.-R., Sih C. J. Stereochemical control of yeast reductions. 6. iastereoselectivity of 2-alkyl-3-oxobutanoate oxido reductases. Tetrahedron: Asymmetry 1993; 4: 1259–1269
  • Takeshita M., Yoshida S. Reduction of N-Oxide with Bakers Yeast. Heterocycles 1990; 30: 1–874
  • Takabe K., Hiyoshi H., Sawada H., Tanaka M., Miyazaki A., Yamada T., Katagiri T., Oda H. Baker's yeast reduction of 3-phenylthiomethyl-2-butenolide and its derivatives: nthesis of versatile chiral C5-building blocks for terpenoid synthesis. Tetrahedron: Asymm. 1992; 3: 99–1400
  • Ticozzi C., Zanarotti A. Baker's yeast reduction of 5-acetyl-2-isoxazolines. Synthesis enantiomerically pure 2,3-dihydroxy ketones and 1,2,4-triols. Tetrahedron Lett. 1988; 29: 6167–6170
  • Trevelyan W. E. Preparation of phosphatidyl inositol from baker's yeast. J. Lipid Res. 1966; 1(7)5–447
  • Xiao X. Y., Prestwich G. D. Enzymatic cyclizations of 26-hydroxy-2,3-oxidosqualenes and 29-hydroxy-2,3-oxidosquaienes give 19-hydroxylanosterols and 21-hydroxylanosterols. Tetrahedron Lett. 1991; 32: 6843–6846
  • Ward O. P., Young C. S. Reductive biotransformations of organic compounds by cells or enzymes of yeast. Enzyme Microb. Technol 1991; 12: 482–493
  • Wu W. I., Lin Y. P., Wang E., Merrill A. H., Carman G. M. Regulation of phosphatidate phosphatase activity from the yeast Saccharomyces cerevisiae by sphingoid bases. J. Biol. Chem. 1993; 268: 13830–13837

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.