1,720,994 research outputs found
Regio- And Enantioselective Reduction Of A α-methyleneketone Byrhodotorula Glutinis
No full textA study of the reduction of 2-ethyl-1-phenylprop-2-en-1-one (3) by Rhodotorula glutinis CCT 2182 in the presence and absence of XAD-7 resin is reported. The use of XAD-7 led to the corresponding (S)-α-methylketone 4 in high yield and enantiomeric excess.200310500506Loughlin, W.A., (2000) Bioresour. Technol., 74, p. 49Siqueira-Filho, E.P., Moran, P.J.S., Rodrigues, J.A.R., (2001) Tetrahedron: Asymmetry, 12, p. 847Siqueira-Filho, E.P., Moran, P.J.S., Rodrigues, J.A.R., (2001) J. Mol. Catal. B: Enzym., 15, p. 23. , and references cited thereinAnastas, P.T., Kirchhoff, M.M., (2002) Acc. Chem. Res., 35, p. 686Patel, R., Hanson, R., Goswami, A., Nanduri, V., Banerjee, A., Donovan, M.J., Goldberg, S., Ko, R., (2003) J. Ind. Microbiol. Biotech., 30, p. 252De Conti, R., Rodrigues, J.A.R., Moran, P.J.S., (2001) Quim. Nova, 24, p. 672Conceiçâo, G.J.A., Moran, P.J.S., Rodrigues, J.A.R., (2003) Tetrahedron: Asymmetry, 14, p. 43Rodrigues, J.A.R., Siqueira-Filho, E.P., Mancilha, M., Moran, P.J.S., (2003) Synth. Commun., 33, p. 333D'Arrigo, P., Fantoni, G.P., Servi, S., Strini, A., (1997) Tetrahedron: Asymmetry, 8, p. 2375D'Arrigo, P., Fuganti, C., Fantoni, G.P., Servi, S., (1998) Tetrahedron, 54, p. 15017Oppolzer, W., Darcel, C., Rochet, P., Rosset, S., De Brabander, J., (1997) Helv. Chim. Acta, 80, p. 131
Enantioselective Reductions Of Ketones Using Baker's Yeast [reduções Enantiosseletivas De Cetonas Utilizando-se Fermento De Pão]
No full textBaker's yeast has been successful employed to reduce carbonyl compounds carrying appropriated substituents at distances under the electronic influence of the keto group. High yields and enantiomeric excess (ee) were obtained with 1,2-alkanedione, 1,2-alkanedione (2-O-methyloxime) and 1,3-alkanedione. Potential chiral building blocks were obtained and applied for stereoselective synthesis of valuable compounds. Evidence for a free radical chain process was obtained with baker's yeast reduction of a-iodoacetophenone using radical inhibitors.246893897Pasteur, L., (1862) C. R., Hebd. Seances Acad. Sci., 55, p. 28Brown, A.J., (1886) J. Chem. Soc., 49, p. 172Boutroux, L., (1880) C. R., Hebd. Seances Acad. Sci., 91, p. 236Bertrand, G., (1896) C. R., Hebd. Seances Acad. Sci., 122, p. 900Dumas, J.B., (1874) Ann. Chim. Phys., 5, p. 3Windisch, W., (1898) Chem. Centr., 1, p. 1214Litner, C.J., Von Liebig, H.J.Z., (1911) Physiol., 72, p. 449Neuberg, C., Welde, E., (1914) Biochem., 60, p. 472Rose, A.H., (1961) Industrial Microbiology, p. 264. , Butterworths: Washington, DCDuran, N., De Conti, R., Rodrigues, J.A.R., (2000) Bol. Soc. Chil. Quim., 45, p. 109Sheldon, R.A., (1993) Chirotecnology, , Marcel Dekker: New YorkWittcoff, H.A., Reuben, B.G., (1996) Industrial Organic Chemicals, , John Wiley & Sons: New YorkAtlas, R.M., (1996) Principles of Microbiology, , McGraw-Hill, Boston, 2a edD'Arrigo, P., Pedrocchi-Fantoni, G., Servi, S., (1997) Adv. Appl. Microbiol., 44, p. 81Czuk, R., Glänzer, B.I., (1991) Chem Rev., 91, p. 49Servi, S., (1990) Synthesis, 1Pereira, R.S., (1995) Quim. Nova, 18, p. 452Santaniello, E., Ferrabochi, P., Grisenti, P., Manzocchi, A., (1992) Chem. Rev., 92, p. 1071Davies, 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 Synthesis, , Katritzky, A. R.Meth-Cohn, O. Rees, C. W., Eds.Academic Press: New YorkStewart, J.D., Reed, K.W., Martinez, C.A., Zhu, J., Chen, G., Kayser, M.M., (1998) J. Am. Chem. Soc., 120, p. 3541Chen, C.S., Zhou, B.N., Girdaukas, G., Shieh, W.R., VanWMiddlesworth, F., Gopalan, A.S., Sih, C.J., (1984) Bioorg. Chem., 12, p. 98Anderson, B.A., Hansen, M.M., Harkness, A.R., Henry, C.L., Vicenzi, J.T., Zmijewski, M.J., (1955) J. Am. Chem. Soc., 117, p. 12358D'Arrigo, P., Fantoni, G.P., Servi, S., Strini, A., (1997) Tetrahedron Asymm., 8, p. 2375D'Arrigo, P., Fuganti, C., Fantoni, G.P., Servi, S., (1998) Tetrahedron, 54, p. 15017MacLeod, R., Prosser, H., Fikentscher, L., Lanyl, J., Mosher, H., (1964) Biochemistry, 3, p. 838De Carvalho, M., Okamoto, M.T., Moran, P.J.S., Rodrigues, J.A.R., (1991) Tetrahedron, 47, p. 2073Moran, P.J.S., Rodrigues, J.A.R., De Carvalho, M., Brenelli, E.C.S., (1995) Some Mechanistic Considerations on the Baker's Yeast Reduction of A-substituted Acetophenones and Propiophenones, p. 499. , Em: Humeres, E. J. J.Ed., Atualidades de Físico-Química Orgânica, UFSC, FlorianópolisEichberger, G., Faber, K., Griengl, H., (1985) Monatsh. Chem., 116, p. 1233Nakamura, K., Ushio, K., Shinzaburo, O., Ohno, A., (1984) Tetrahedron Lett., 25, p. 3979Brenelli, E.C.S., De Carvalho, M., Okubo, M.T., Marques, M., Moran, P.J.S., Rodrigues, J.A.R., Sorrilha, A.E.P.M., (1992) Indian J. Chem., 31 B, p. 821Emerson, W.S., (1945) J. Am. Chem. Soc., 67, p. 516Ranieri, R.L., McLauglin, J.L., (1977) Lloydia, 67, p. 173Aleixo, L.M., De Carvalho, M., Moran, P.J.S., Rodrigues, J.A.R., (1993) BioOrg. Med. Chem. Lett., 3, p. 1637Fronza, G., Fuganti, C., Grasselli, P., Mele, A., (1991) J. Org. Chem., 56, p. 6019Cabon, O., Larchevêque, M., Buisson, D., Azerad, R., (1992) Tetrahedron Lett., 33, p. 7337Cabon, O., Larchevêque, M., Buisson, D., Azerad, R., (1995) Tetrahedron Asymm., 6, p. 2199Besse, P., Renard, M.F., Veschambre, H., (1994) Tetrahedron Asymm., 5, p. 1249Brenelli, E.C.S., Moran, P.J.S., Rodrigues, J.A.R., (1990) Synth. Commun., 20, p. 261Deol, B.S., Ridley, D.D., Simpson, G.W., (1976) Aust. J. Che,., 29, p. 2459Iriuchijima, S., Ogawa, M., (1982) Synthesis, 41Wendhausen Jr., R., Moran, P.J.S., Joekes, I., Rodrigues, J.A.R., (1998) J. Mol. Cat. BEnzymatic, 5, p. 69Buehler, E., (1967) J. Org. Chem., 32, p. 261Slater, W.K., (1920) J. Chem. Soc., 116, p. 587Kreutz, O.C., Segura, R.C.M., Rodrigues, J.A.R., Moran, P.J.S., (2000) Tetrahedron Asymm., 11, p. 2107Kreutz, O.C., Moran, P.J.S., Rodrigues, J.A.R., (1997) Tetrahedron Asymm., 8, p. 2649Pines, S.H., Chemerda, J.M., Kozlowski, M.A., (1966) J. Org. Chem., 31, p. 3466Corey, E.J., Richman, J.E., (1970) J. Am. Chem. Soc., 92, p. 5276Singh, L., Ram, R.N., (1993) Synth. Commun., 23, p. 3139Wali, A., Ganeshpure, P.A., Saish, S., (1993) Bull. Chem. Soc. Jpn., 66, p. 1847Fauve, A., Veschambre, H., (1988) J. Org. Chem., 53, p. 5215Nakamura, K., Inoue, K., Ushio, K., Oka, S., Ohno, A., (1988) J. Org. Chem., 53, p. 2589Fuganti, C., Grasselli, P., Casati, R., Carmeno, M., (1985) Tetrahedron Lett., 107, p. 101Nakamura, K., Kawai, Y., Oka, S., Ohno, A., (1989) Bull. Chem. Soc. Jpn., 62, p. 875Nakamura, K., Higaki, M., Ushio, K., Oka, S., Ohno, A., (1985) Tetrahedron Lett., 26, p. 4213Cui, J.-N., Ema, T., Sakai, T., Utaka, M., (1998) Tetrahedron Asymm., 9, p. 2681Rotthaus, O., Kuger, D., Demuth, M., Schaffner, K., (1997) Tetrahedron, 53, p. 935Fraga, C.A.M., Barreiro, E.J., Da Silva, E.F., Dos Santos, A.R., Ramos, I.D.K.V., Neto, F.R.D., (1997) Chirality, 9, p. 321Braga, A.C.H., Harris, M.I., (1993) Indian J. Chem., 32 B, p. 101Ushio, K., Inoue, K., Nakamura, K., Oka, S., Ohno, A., (1986) Tetrahedron Lett., 27, p. 2657Nakamura, K., Inoue, K., Ushio, K., Oka, S., Ohno, A., (1987) Chem. Lett., 679noteFantin, G., Fogagnolo Guerzoni, M.E., Lanciotti, R., Medici, A., Pedrini, P., Rossi, D., (1996) Tetrahderon Asymm., 7, p. 2879Pereira, R.S., Pavão, F., Oliva, G., (1998) Mol. Cell. Biochem., 178, p. 27Chenevert, R., Fortier, G., (1991) Chem. Lett., p. 1603Pilli, R.A., Riatto, V.B., (1999) J. Braz. Chem. Soc., 10, p. 363Pilli, R.A., Riatto, V.B., (1998) J. Braz. Chem. Soc., 9, p. 571Fuganti, C., Serra, S., (2000) J. Chem. Soc., Perkin Trans I, p. 97Watanabe, H., Shimizu, H., Mon, K., (1994) Synthesis, p. 1249Fadnavis, N.W., Vadivel, S.K., Sharfuddin, M., Bhalerao, U.T., (1997) Tetrahedron Asymm., 8, p. 4003Kayser, M., Mihovilovic, M.D., Kearns, J., Feicht, A., Stewart, J.D., (1999) J. Org. Chem., 64, p. 6603Tsuboi, S., Sakamoto, J., Yamashita, H., Sakai, T., Utaka, M., (1998) J. Org. Chem., 63, p. 1102Knight, D.W., Lewis, N., Share, A.C., Haigh, D., (1998) J. Chem. Soc., Perkin Trans I, p. 367
A Simple Method For Mild Oxidation Of α-hydroxysilanes To Provide Aroylsilanes
No full textPotassium permanganate supported onto alumina in hexane-water is a good oxidizing agent to convert α-hydroxysilanes into acylsilanes. This mild oxidation afforded aroylsilanes having electron-donating groups attached to the aromatic ring, in 70-86% yield.311624572461Saleur, D., Bouillon, J.-P., Portella, C., (1999) Tetrahedron Lett., 40, p. 321Saleur, D., Bouillon, J.-P., Portella, C., (2000) Tetrahedron Lett., 41, p. 1885Tsai, Y.M., Cherng, C.D., Nieh, H.C., Sieh, J.A., (1999) Tetrahedron, 55, p. 14587Takeda, K., Ohtani, Y., (1999) Org. Lett., 1, p. 677Chuang, T.-H., Fang, J.-M., Jiaang, W.-T., Tsai, Y.-M., (1996) J. Org. Chem., 61, p. 1794Chang, S.Y., Jiaang, W.T., Cherng, C.D., Tang, K.H., Huang, C.H., Tsai, Y.M., (1997) J. Org. Chem., 62, p. 9089Tsai, Y.M., Tang, K.H., Jiaang, W.T., (1996) Tetrahedron Lett., 37, p. 7767Nakada, M., Urano, Y., Kobayashi, S., Ohno, M., (1994) Tetrahedron Lett., 35, p. 741Fleming, I., Barbero, A., Walter, D., (1997) Chem. Rev., 97, p. 995Bonini, B.F., Comes-Franchini, M., Laboroi, F., Mazzanti, G., Ricci, A., Varchi, G., (1999) J. Org. Chem., 64, p. 8008Huang, A.X., Xiong, Z., Corey, E.J., (1999) J. Am. Chem. Soc., 121, p. 9999Patrocínio, A.F., Corrêa I.R., Jr., Moran, P.J.S., (1999) J. Chem. Soc. Perkin Trans. 1, p. 3133Tacke, R., Linoh, H., (1989) The Chemistry of Organic Silicon Compounds, , Patai, S.Rappoport, Z. (eds), Chap. 18. John Wiley & Sons LtdSyldatk, C., Stoffregen, A., Wuttke, F., Tacke, R., (1988) Biotech. Letters, 10, p. 731Fischer, L., Wagner, S.A., Tacke, R., (1995) Appl. Microbiol. Biotechnol., 42, p. 671Tacke, R., Wagner, S.A., Brakmann, S., Wuttke, F., (1993) J. Organomet. Chem., 458, p. 13Brook, A.G., (1968) Advance Organo-metallic Chemistry, 7, p. 95. , Stone, F.G.A.West, R. eds. Ac. Press, N.YPage, P.C.B., Klair, S.S., Rosenthal, S., (1990) Chem. Soc. Rev., 19, p. 147Ricci, A., Degl'Innocenti, A., (1989) Synthesis, p. 647Ricci, A., (1998) J. Organomet. Chem., 567, p. 181Patrocinio, A.F., Moran, P.J.S., (2001) J. Braz.Chem. Soc., 12, p. 7Patrocínío, A.F., Moran, P.J.S., (2000) J. Organomet. Chem., 603, p. 220Tius, M.A., Hu, H., (1998) Tetrahedron Lett., 39, p. 5937Stergiades, I.A., Tius, M.A., (1999) J. Org. Chem., 64, p. 7547Geng, F., Maleczka R.E., Jr., (1999) Tetrahedron Lett., 40, p. 3113Fleming, I., Ghosh, U., (1994) J. Chem. Soc. Perkin Trans. 1, p. 257Paredes, M.D., Alonso, R., (1999) Tetrahedron Lett., 40, p. 3973Bonini, B.F., Franchini, M.C., Mazzanti, G., Passamonti, U., Ricci, A., Zani, P., (1995) Synthesis, 92Sakaguchi, K., Mano, H., Ohfune, Y., (1998) Tetrahedron Lett., 39, p. 4311Sommer, L.H., Bailey, D.L., Golberg, G.M., Buck, C.E., Bye, T.S., Evans, F.J., Whitmore, F.C., (1954) J. Am. Chem. Soc., 76, p. 1613Ireland, R.E., Norbeck, D.W., (1985) J. Org. Chem., 50, p. 2198Linderman, R.J., Suhr, Y., (1998) J. Org. Chem., 53, p. 31569Danheiser, R.L., Fink, D.M., Okano, K., Tsai, Y.-M., Szczepanski, S.W., (1985) J. Org. Chem., 50, p. 5393Huber, P., Bratovanov, S., Bienz, S., Syldatk, C., Pietzsch, M., (1996) Tetrahedron: Asymmetry, 7, p. 69Mori, A., Fujita, A., Ikegashira, K., Nishihara, Y., Hiyama, T., (1997) Synlett., p. 693Wilson, S.R., Hague, M.S., Misra, R.N., (1982) J. Org. Chem., 47, p. 747Barretm, A.G.M., Hill, J.M., Wallace, E.M., Flygare, J.A., (1991) Synlett., p. 764Hudrlik, P.F., Abdallah, Y.M., Kulkarni, A.K., Hudrlik, A.M., (1992) J. Org. Chem., 57, p. 6552Hiyama, T., Obayashi, M., (1983) J. Org. Chem., 48, p. 912Linderman, R.J., Ghannam, A., (1990) J. Am. Chem. Soc., 112, p. 2392Linderman, R.J., Chen, K., (1992) Tetrahedron Lett., 33, p. 6767notePatrocínio, A.F., Moran, P.J.S., (2000) Synth. Commun., 30, p. 1419notenot
Bioreduction Of α-haloacetophenones By Rhodotorula Glutinis Andgeotrichum Candidum
No full textEnantioselective reductions with enantiocomplementarity of α-haloacetophenones by Rhodotorula glutinis CCT 2182 and Geotrichum candidum CCT 1205 afforded the corresponding (R)- and (S)-halohydrins (halo = Cl, Br and I), respectively, in high chemical yields (89-99%) and enantiomeric excesses (92-99%). These halohydrins are potential chiral building blocks for the stereoselective syntheses of valuable compounds.200310404410Carvalho, M., Okamoto, M.T., Moran, P.J.S., Rodrigues, J.A.R., (1991) Tetrahedron, 47, pp. 2073-2080Sorrilha, A.E.P.M., Marques, M., Joekes, I., Moran, P.J.S., Rodrigues, J.A.R., (1992) Bioorg. Med. Chem. Lett., 2, pp. 191-196Sakai, T., Wada, K., Murakami, T., Kohra, K., Imajo, N., Ooga, Y., Tsuboi, S., Utaka, M., (1992) Bull. Chem. Soc. Jpn., pp. 631-638Besse, P., Sokoltchik, T., Veschambre, H., (1998) Tetrahedron Asymmetry, 9, pp. 4441-4457Wei, Z.-L., Li, Z.-Y., Lin, G.-Q., (1998) Tetrahedron, 54, pp. 13059-13072Barbiere, C., Bossi, L., D'Arrigo, P., Fantoni, G.P., Servi, S., (2001) J. Mol. Catal.: B Enzym., 11, pp. 415-421Ni, Y., Xu, J.-H., (2002) J. Mol. Catal.: B Enzym., 12, pp. 233-241Corey, E.J., Link, J.O., (1990) Tetrahedron Lett., 31, pp. 601-604Brenelli, E.C.S., Carvalho, M., Okubo, M.T., Marques, M., Moran, P.J.S., Rodrigues, J.A.R., Sorrilha, A.E.P.M., (1992) Indian J. Chem., 31 B, pp. 821-823Aleixo, L.M., Carvalho, M., Moran, P.J.S., Rodrigues, J.A.R., (1993) Bioorg. Med. Chem. Lett., 3, pp. 1637-1642Ohno, A., (1999) Rev. Heteroatom Chem., 20, pp. 29-68Nakamura, K., Fujii, M., Ida, Y., (2001) Tetrahedron Asymmetry, 12, pp. 3147-3153Salvi, N.A., Chattopadhyay, S., (2001) Tetrahedron, 57, pp. 2833-2839Comasseto, J.V., Omori, A.T., Andrade, L.H., Porto, A.L.M., (2003) Tetrahedron Asymmetry, 14, pp. 711-715Prelog, V., (1964) Pure Appl. Chem., 9, pp. 119-130noteNakamura, K., Inoue, Y., Matsuda, T., Ohno, A., (1995) Tetrahedron Lett., 36, pp. 6263-6266Tanner, D.D., Singh, H.K., Kharrat, A., Stein, A.R., (1987) J. Org. Chem., 52, pp. 2142-2146Tanner, D.D., Singh, H.K., (1986) J. Org. Chem., 51, pp. 5182-5186Tanner, D.D., Stein, A.R., (1988) J. Org. Chem., 53, pp. 1642-1646Tanner, D.D., Kharrat, A., (1988) J. Org. Chem., 53, pp. 1646-1650Smolen, J.M., Weber, E.J., Tratnyek, P.G., (1999) Environ. Sci. Technol., 33, pp. 440-445Ohno, A., Kito, N., (1972) Chem. Lett., pp. 369-372Ohno, A., Yamamoto, H., Oka, S., (1981) J. Am. Chem. Soc., 103, pp. 2041-2045http://www.fat.org.br/, Rua Latino Coelho 1301, 13087-010 Campinas-SP, Brazi
Protection Studies Of Saccharomyces Cerevisiae Cells For The Use In Reduction Reactions In Organic Media [estudos De Proteção Da Célula De Saccharomyces Cerevisiae Para Utilização Em Reações De Redução Em Meio Orgânico]
No full textNew methodologies for protection of Saccharomyces cerevisiae (FP) cells when supported in montmorillonite K10 (K10), recovered or not with gelatin (G) and in the presence or absence of sucrose (S) are presented. These systems were used for the enantioselective reduction of ethyl acetoacetate and α-chloroacetophenone in hexane, under FP/K10/G/S and FP/S at 20°C during 24 hours, affording S-(+)-ethyl-3-hydroxybutanoate in 100% conversion and 99% ee, and R-(-)-2-chloro-1-phenylethanol 79% and 78% ee at 20 and 30°C, respectivelly.254567571Bon, E.P.S., Pereira N., Jr., (1999) Tecnologia Enzimática, p. 113. , Fundação Biblioteca NacionalRio de Janeiro, RJSantaniello, E., Ferraboschi, P., Grisenti, P., Manzocchi, A., (1992) Chem. Rev., 92, p. 1071Roberts, S.M., Turner, N.J., Willetts, J., Turner, M.K., (1995) Introduction to Biocatalysis using Enzymes and Micro-organisms, p. 195. , Cambridge University Press: New YorkHudlicky, T., Gonzalez, D., Gibson, D.T., (1999) Aldrichimica Acta, 32, p. 35Duran, N., De Conti, R., Rodrigues, J.A.R., (2000) Bol. Soc. Chil. Quim., 45, p. 109Stewart, J.D., (2000) Curr. Opin. Biotechnol., 11, p. 363Stanley, M.R., (2000) J. Chem. Educ., 77, p. 344Rotthaus, O., Krüger, D., Demuth, M., Schaffner, K., (1997) Tetrahedron, 53, p. 935Hudlicky, T., Gonzalez, D., Gibson, D.T., (1999) Aldrichimica Acta, 32, p. 35Fernadez-Lafuente, R., Armisén, P., Sabuquillo, P., Fernández-Lorente, G., Guisán, J.M., (1998) Chem. Phys. Lipids, 93, p. 185Narvátil, M., Sturdik, E., (1999) Biologia, 54, p. 635D'Arrigo, P., Fantoni, G.P., Servi, S., Strinti, A., (1997) Tetrahedron: Asymmetry, 8, p. 2375Hayakawa, R., Nozawa, K., Shimizu, M., Fujisawa, T., (1998) Tetrahedron Lett., 39, p. 67Pereira, R.S., (1998) Crit. Rev. Biotechnol., 18, p. 25Dahl, A.C., Madsen, J.O., (1998) Tetrahedron: Asymmetry, 6, p. 4395Bekatorou, A., Koutinas, A.A., Kaliafas, A., Kanellaki, M., (2001) Process Biochem., 36, p. 549Grunwald, P., (2000) Biochem. Educ., 28, p. 96Nakamura, K., Kondo, S., Kawai, Y., Ohno, A., (1991) Tetrahedron Lett., 32, p. 7075León, R., Fernandes, P., Pinheiro, H.M., Cabral, J.M., (1998) Enzyme Microb. Technol., 23, p. 483Jayasinghe, L.Y., Kodituwakku, D., Smallridge, A.J., Trewhella, M.A., (1994) Bull. Chem. Soc. Jpn., 67, p. 2528Nakamura, K., Kondo, S., Kawai, Y., Ohno, A., (1993) Bull. Chem. Soc. Jpn., 66, p. 2738Faber, K., (1997) Biotransformations in Organic Chemistry, p. 402. , Springer-Verlag: BerlinMedson, C., Smallridge, A.J., Trewhella, M.A., (1997) Tetrahedron: Asymmetry, 8, p. 1049Kanda, T., Miyata, N., Fukui, T., Kawamoto, T., Tanaka, A., (1998) Appl. Microbiol. Biotechnol., 49, p. 377Medson, C., Smallridge, A.J., Trewhella, M.A., (2001) J. Mol. Catal. B: Enzym., 11, p. 897Athanasiou, N., Smallridge, A.J., Trewhella, M.A., (2001) J. Mol. Catal. B: Enzym., 11, p. 893Dumanski, P.G., Florey, P., Knettig, M., Smallridge, A.J., Trewhella, M.A., (2001) J. Mol. Catal. B: Enzym., 11, p. 905Furniss, B.S., Hannaford, A.J., Rogers, V., Smith, P.W.G., Tatchell, A.R., (1978) Vogel's Textbook of Practical Organic Chemistry, 4 a ed., p. 353. , Longman Group Limited: New York(1979) Handbook of Chemistry and Physics, , CRC Press: Boca RatonSorrilha, A.E.P.M., Marques, M., Joekes, I., Moran, P.J.S., Rodrigues, J.A.R., (1992) Bioorg. Med. Chem. Lett., 2, p. 191Moran, P.J.S., Rodrigues, J.A.R., Joekes, I., Brenelli, E.C.S., Leite, R.A., (1994) Biocatalysis, 9, p. 321Wendhausen R., Jr., Moran, P.J.S., Joekes, I., Rodrigues, J.A.R., (1998) J. Mol. Catal. B: Enzym., 5, p. 69Brenelli, E.C.S., Carvalho, M., Okubo, M.T., Marques, M., Moran, P.J.S., Rodrigues, J.A.R., (1992) Indian J. Chem., 31 B, p. 821Barbieri, C., Bossi, L., D'Arrigo, P., Fantoni, G.P., Servi, S., (2001) J. Mol. Catal. B: Enzym., 11, p. 415Carvalho, M., Okamoto, M.T., Moran, P.J.S., Rodrigues, J.A.R., (1991) Tetrahedron, 47, p. 2073Aleixo, L.M., Carvalho, M., Moran, P.J.S., Rodrigues, J.A.R., (1993) Bioorg. Med. Chem. Lett., 3, p. 1637Moran, P.J.S., Rodrigues, J.A.R., Carvalho, M., De Brenelli, E.C.S., (1995) Atualidades de Físico Química Orgânica, p. 499. , Ed. E. Humeres: Florianópoli
Chemoenzymatic Syntheses Of (r)-2-bromo-, (r)2-chloro- And (r)2-azido-1-(1,3-benzodioxol-5-yl)-1-ethanol
No full textEnantioselective reductions of 2-X-1-(1,3-benzodioxol-5-yl)-1-ethanones, (X = Cl, Br, N 3) by Rhodothorula glutinis CCT 2182 afforded the corresponding (R)-ethanols in good to excellent yields (57-99%) and excellent enantiomeric excesses (>99%). These alcohols may be used as raw materials for the preparation of the pharmaceuticals (R)-(-)-epinephrine, (R)-(-)-norepinephrine and (R)-(-)-isoproterenol. © 2004 Elsevier Ltd. All rights reserved.151726152620Ager, D.J., Prakash, I., Schaad, D.R., (1996) Chem. Rev., 96, pp. 835-875Kanerva, L.T., (1996) Acta Chem. Scand., 50, pp. 234-242Armstrong, D.W., He, L., Yu, T., Lee, J.T., Liu, Y., (1999) Tetrahedron: Asymmetry, 10, pp. 37-60Bergmeier, S.C., (2000) Tetrahedron, 56, pp. 2561-2576Nakamura, Y., Takeuchi, S., Okumura, K., Ohgo, Y., (2001) Tetrahedron, 57, pp. 5565-5571Xu, D.C., Du, D.M., Ji, N., Wang, I.V., Hua, W.T., (2003) Synth. Commun., 33, pp. 2563-2574Gomez, M., Philipport, K., Colliere, V., Lecante, P., Muller, G., Chaudret, B., (2003) New J. Chem., 27, pp. 114-120Carvalho, M., Okamoto, M.T., Moran, P.J.S., Rodrigues, J.A.R., (1991) Tetrahedron, 47, pp. 2073-2080Fardelone, L.C., Rodrigues, J.A.R., Moran, P.J.S., (2003) Arkivoc, 10, pp. 404-410Moran, P.J.S., Rodrigues, J.A.R., Joekes, I., Brenelli, E.C.S., Leite, R.A., (1994) Biocatalysis, 9, p. 321Siqueira Filho, E.P., Rodrigues, J.A.R., Moran, P.J.S., (2001) J. Mol. Catal. B: Enzym., 15, pp. 23-28Brenelli, E.C.S., Carvalho, M., Okubo, M.T., Marques, M., Moran, P.J.S., Rodrigues, J.A.R., Sorrilha, E.P.M., (1992) Indian J. Chem., 31, pp. 821-823Barbieri, C., Bossi, L., D'Arrigo, P., Fantoni, G.P., Servi, S., (2000) J. Mol. Catal. B: Enzym., 11, pp. 415-421Romero, M.C., Hammer, E., Cazau, M.C., Arambarri, A.M., (2002) Environ. Pollut., 118, pp. 379-382Smit, M.S., (2004) Trends Biotechnol., 22, pp. 123-129Yeates, C.A., Van Dyk, M.S., Botes, A.L., Breytenbach, J.C., Krieg, H.M., (2003) Biotechnol. Lett., 25, pp. 675-680Kronenburg, N.A.E., Bont, J.A.M., (2001) Enzyme Microb. Technol., 28, pp. 210-217Cagnon, J.R., Porto, A.L.M., Marsaioli, A.J., Manfio, G.P., Eguchi, S.Y., (1999) Chemosphere, 38, pp. 2237-2242Rubio, M.C., Runco, R., Navarro, A.R., (2002) Phytochemistry, 61, pp. 605-609Cabon, O., Larchevê, R., (1992) Tetrahedron Lett., 33, pp. 7337-7340Brzezinska-Rodak, M., Zymanczyk-Duda, E., Kafarski, P., Lejczak, B., (2002) Biotechnol. Prog., 18, pp. 1287-1291Goswami, A., Mirfakhrae, K.D., Totleben, M.J., Swaminathan, S., Patel, R.N., (2001) J. Ind. Microbiol. Biotech., 26, pp. 259-261Patel, R.N., Goswami, A., Chu, L., Donovan, M.J., Nanduri, V., Golberg, S., Johnston, R., Mueller, R., (2004) Tetrahedron: Asymmetry, 15, pp. 1247-1258Homann, J.M., Vail, R.B., Previde, E., Tamarez, M., Morgan, B., Dodds, D.R., Zaks, A., (2004) Tetrahedron, 60, pp. 789-797Conceiao, G.J.A., Moran, P.J.S., Rodrigues, J.A.R., (2003) Arkivoc, 10, pp. 500-506Hayashi, T., Katsumura, A., Konishi, M., Kumada, M., (1979) Tetrahedron Lett., 20, pp. 425-428Corey, E.J., Link, J.O., (1990) Tetrahedron Lett., 31, pp. 601-604Hong, Y., Gao, Y., Nie, X., Zepp, C.M., (1994) Tetrahedron Lett., 35, pp. 5551-5554Singer, R.A., Carreira, E.M., (1997) Tetrahedron Lett., 38, pp. 927-930Gringauz, A., (1997) Introduction to Medicinal Chemistry: How Drugs Act and Why?, , Wiley-VCH New YorkKirk, K.L., Biomedical Chemistry Applying Chemical Principles to the Understanding and Treatment of Disease (2000) Fluorine Substitution As a Modulator of Biological Processes, , P.F. Torrence Wiley-Interscience New YorkKaufman, P.R., Wyman, D.P., (1964) J. Org. Chem., 29, pp. 1956-1960Effenberger, F., Hársch, B., Ziegler, T., (1990) Synthesis, 7, pp. 575-578Ohta, H., Miyamae, Y., Tsuchihashi, G., (1989) Agric. Biol. Chem., 53, pp. 281-283Tanner, D.D., Singh, H.K., (1986) J. Org. Chem., 51, pp. 5182-5186Tanner, D.D., Singh, H.K., Kharrat, A., Stein, A.R., (1987) J. Org. Chem., 52, pp. 2142-2146Tanner, D.D., Stein, A.R., (1988) J. Org. Chem., 53, pp. 1642-1646Tanner, D.D., Kharrat, A., (1988) Org. Chem., 53, pp. 1646-1650Adam, W., Heil, M., Hutterer, R., (1992) J. Org. Chem., 57, pp. 4491-4495Aleixo, L.M., Carvalho, M., Moran, P.J.S., Rodrigues, J.A.R., (1993) Bioorg. Med. Chem. Lett., 3, pp. 1637-1642Jorg, G., Bertau, M., (2004) ChemBioChem, 4, pp. 87-92Eichberger, G., Faber, K., Griengl, H., (1985) Monatsh. Chem., 116, pp. 1233-1236Wendhausen Jr., R., Moran, P.J.S., Joekes, I., Rodrigues, J.A.R., (1988) J. Mol. Catal. B: Enzym., 5, pp. 69-73Prelog, V., (1964) Pure Appl. Chem., 9, pp. 119-130Sih, C., Chen, C.S., (1984) Angew. Chem., Int. Ed., 23, pp. 570-578http://www.fat.org.br/, Fundação André Tosello Pesquisa e Tecnologia, Rua Latino Coelho 1301, 13087-010 Campinas-SP, Brazi
Continuous Process For Large-scale Preparation Of Chiral Alcohols With Baker's Yeast Immobilized On Chrysotile Fibers
No full textBioreductions of prochiral ketones in a continuous process were carded out in a Packed-bed-reactor with baker's yeast (Saccharomyces cerevisiae) immobilized on chrysotile fibers (IMBY). The performance of the reactor was observed for 30 days, under a constant dilution rate of 1.7 x 10-1 h-1 using ethylbenzoylformate as substrate. The steady state showed 2.9 x 10-2 g l-1 h-1 of productivity, 50% chemical yield, and 90% ee (enantiometric excess). Using ethylacetoacetate at the same dilution rate for 8 days, the steady state showed 65% chemical yield and 95% ee. No significant change on the IMBY integrity was observed. The results show that chrysotile is an excellent carrier for immobilization of baker's yeast (BY) cells to be used in the continuous process of bioreduction.51-46973Wong, C.H., Whitesides, G.M., (1994) Enzymes in Synthetic Organic Chemistry, p. 131. , Pergamon, OxfordServi, S., (1990) Synthesis, 1Csuc, R., Glanzer, B., (1991) Chem. Rev., 91, p. 49Santaniello, E., Ferraboschi, P., Grisenti, P., Manzocchi, A., (1992) Chem. Rev., 92, p. 1071Kometani, T., Yoshii, H., Matsuno, R., (1996) J. Mol. Catal. B: Enzymatic, 1, p. 45Rogers, P.L., Shin, H.S., Wang, B., (1997) Adv. Biochem. Eng. Biotechnol., 51, p. 33Sakai, T., Nakamura, T., Fukuda, K., Amano, E., Utaka, M., Takeda, A., (1986) Bull. Chem. Soc. Jpn., 59, p. 3185Naoshima, Y., Hasegawa, H., (1987) Chem. Lett., p. 2379Naoshima, Y., Hasegawa, H., Saeki, T., (1987) Agric. Biol. Chem., 51, p. 3417Nakamura, K., Inoue, K., Ushio, K., Oka, S., Ohno, A., (1988) J. Org. Chem., 53, p. 2589Naoshima, Y., Hasegawa, H., Nishiyama, T., Nakamura, A., (1989) Bull. Chem. Soc. Jpn., 62, p. 608Nakamura, K., Miyai, T., Inoue, K., Kawasaki, S., Oka, S., Ohno, A., (1990) Biocatalysis, 3, p. 17Furasaki, S., Seki, M., (1992) Adv. Biochem. Eng. Biotech., 46, p. 161Moran, P.J.S., Rodrigues, J.A.R., Joekes, I., Brenelli, E.C.S., Leite, R.A., (1994) Biocatalysis, 9, p. 321Sorrilha, A.E.P.M., Marques, M., Joekes, I., Moran, P.J.S., Rodrigues, J.A.R., (1992) Bioorg. Med. Chem. Lett., 2, p. 19Parizotto O., Jr., Comerlato, M.H., Pedroso, P.R., Moran, P.J.S., Carvalho, M., Joekes, I., Pat. BRPI8.903.849-5 (1989)Joekes, I., Rodrigues, J.A.R., Moran, P.J.S., Wendhausen R., Jr., Pat. BR PI9700635 (1997)Kometani, T., (1989) Chem. Lett., p. 1465Turner, N., (1994) Chem. Ind., 15, p. 59
Bioreduction Of α-methyleneketones
No full textBioreduction of methyleneketones was carried out with Rhizopus arrhizus, Pseudomonas fluorescens and immobilized Saccharomyces cerevisae. The α-substituted enones were enantioselectively reduced to saturated ketones with good to excellent ee, depending of microorganism. With the S. cerevisae good ee (12-93%) was obtained while excellent ee (99%) was achieved with P. fluorescens.200168593Roberts, M.S., (2000) J. Chem. Soc., Perkin Trans. 1, pp. 611-633Pereira, R.S., (1988) Crit. Rev. Biotechnol., 18, p. 25Roberts, S.M., Turner, N.J., Willets, A.J., Turner, M.K., (1995) Introduction to Biocatalysis Using Enzymes and Micro-Organisms, , Cambridge University Press: New YorkFaber, K., (1995) Biotransformations in Organic Chemistry, 2nd Edn., , Springer, BerlinDuran, N., De Conti, R., Rodrigues, J.A.R., (2000) Bol. Soc. Chil. Quim., 45, pp. 109-121Kreutz, O.C., Segura, R.C.M., Rodrigues, J.A.R., Moran, P.J.S., (2000) Tetrahedron Asymm., 11, pp. 2107-2115Czuk, R., Glänzer, B.I., (1991) Chem. Rev., 91, pp. 49-97Servi, S., (1990) Synthesis, pp. 1-25Kayser, M.M., Mihovilovic, M.D., Kearns, J., Feicht, A., Stewart, J.D., (1999) J. Org. Chem., 64, pp. 6603-6608Dao, D.H., Okamura, M., Akasaka, T., Kawai, Y., Hida, K., Ohno, A., (1998) Tetrahedron Asymm., 9, pp. 2725-2737D'Arrigo, P.D., Pedrocchi, G., Servi, S., (1997) Adv. Appl. Microbiol., 44, pp. 81-123Utaka, M., Onoue, S., Takeda, A., (1987) Chem. Lett., pp. 971-972Sato, T., Hanayama, K., Fujisawa, T., (1988) Tetrahedron Lett., 29, pp. 2197-2200Sakai, T., Matsumoto, S., Hidaka, S., Imajo, N., Tsuboi, S., Utaka, M., (1991) Bull. Chem. Soc. Jpn., 64, pp. 3473-3475Ferraboshi, P., Reza-Elahi, S., Verza, E., Santaniello, (1999) Tetrahedron Asymm., 10, pp. 2639-2642Siqueira Filho, E.P., Rodrigues, J.A.R., Moran, P.J.S., (2001) J. Mol. Catal. B: Enzymatic, 618, pp. 1-6Mori, K., Harashima, S., (1991) Tetrahedron Lett., 32, pp. 5995-5998Cywin, C.L., Kallmerten, J., (1991) J. Nat. Prod., 54, pp. 1664-1667Shimizu, I., Hayashi, K., Ide, N., Oshima, M., (1991) Tetrahedron, 47, pp. 2992-2998Tatsuta, K., Masuda, N., Nishida, H., (1998) Tetrahedron Lett., 39, pp. 83-86Chida, N., Yoshinaga, M., Tobe, T., Ogawa, S., (1997) Chem. Commun., pp. 1043-1044Nakajima, N., Ubukata, M., Yonemitsu, O., (1997) Heterocycles, 46, pp. 105-110Tye, H., (2000) J. Chem. Soc., Perkin Trans. 1, pp. 275-289. , and references there inTramontini, M., Angiolini, L., (1994) Mannich Bases, Chemistry and Uses, , CRC Press: Boca RatonRodrigues, J.A.R., Siqueira-Filho, E.P., Mancilha, M.D., Moran, P.J.S., Synth. Commun., , in pressKim, M.Y., Lim, G.J., Lim, J.I., Kim, D.S., Kim, I.Y., Yang, J.S., (1997) Heterocycles, 45, pp. 2041-2043Sorrilha, A.E.P.M., Marques, M., Joekes, I., Moran, P.J.S., Rodrigues, J.A.R., (1992) Biorg. Med. Chem. Lett., 2, pp. 191-196Nakamura, K., Ushio, K., Oka, S., Ohno, A., (1984) Tetrahedron Lett., 25, pp. 3979-3982Oppolzer, W., Darcel, C., Rochet, P., Rosset, S., Brabander, J.D., (1997) Helv. Chim. Acta, 80, pp. 1319-1337Blanco, L., Rousseau, G., Barnier, J.-P., Guibé-Jampel, E., (1993) Tetrahedron Asymm., 4, pp. 783-792Mitteilung, K., Eichberger, G., Faber, K., Griengl, H., (1985) Monatsch. Chem., 116, pp. 1233-1236Manzocchi, A., Casati, R., Fiecchi, A., Santaniello, E.J., (1987) J. Chem. Soc., Perkin Trans. 1, pp. 2753-2757Nájera, C., Sansano, J.M., (1990) Tetrahedron, 46, pp. 3993-4002Suzuki, T., Ohwada, T., Shudo, K., (1997) J. Am. Chem. Soc., 119, pp. 6774-6780Paterson, I., (1988) Tetrahedron, 44, pp. 4207-4219Kissman, H.M., Williams, J.W., (1950) J. Am. Chem. Soc., 72, p. 532
Crystal Structure Of (3e)-3-(2,4-dinitrophenoxymethyl)-4-phenylbut-3-en-2-one
Get PDFIn the title compound, C17H14N2O6, the conformation about the C=C double bond [1.345(2)Å] is E, with the ketone moiety almost coplanar [C-C-C-C torsion angle = 9.5(2)°] along with the phenyl ring [C-C-C-C = 5.9(2)°]. The aromatic rings are almost perpendicular to each other [dihedral angle = 86.66(7)°]. The 4-nitro moiety is approximately coplanar with the benzene ring to which it is attached [O-N-C-C = 4.2(2)°], whereas the one in the ortho position is twisted [O-N-C-C = 138.28(13)°]. The molecules associate via C-H⋯O interactions, involving both O atoms from the 2-nitro group, to form a helical supramolecular chain along [010]. Nitro-nitro N⋯O interactions [2.8461(19)Å] connect the chains into layers that stack along [001].709o1051o1052Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.L., Giacovazzo, C., Guagliardi, A., Moliterni, A.G.G., Spagna, R., (1999) J. Appl. Cryst, 32, pp. 115-119Brandenburg, K., (2006) DIAMOND, , Crystal Impact GbR, Bonn, Germany(2009) APEX2 and SAINT, , Bruker Bruker AXS Inc., Madison, Wisconsin, USA(2010) ChemAxon, , http://www.chemaxon.com, MarvinsketchDaszkiewicz, M., (2013) CrystEngComm, 15, pp. 10427-10430Farrugia, L.J., (2012) J. Appl. Cryst, 45, pp. 849-854Gans, J., Shalloway, D., (2001) J. Mol. Graph. Mode, 119, pp. 557-559De Paula, B.R.S., Zampieri, D.S., Rodrigues, J.A.R., Moran, P.J.S., (2013) Tetrahedron Asymmetry, 24, pp. 973-981Rodrigues, J.A.R., Moran, P.J.S., Conceicaõ, G.J.A., Fardelone, L.C., (2004) Food Technol. Biotechno, 142, pp. 295-303Sheldrick, G.M., (1996) SADABS, , University of Göttingen, GermanySheldrick, G.M., (2008) Acta Cryst A, 64, pp. 112-122Westrip, S.P., (2010) J. Appl. Cryst, 43, pp. 920-925Zukerman-Schpector, J., Maganhi, S.H., Moran, P.J.S., De Paula, B.R.S., Nucci, P.R., Tiekink, E.R.T., (2014) Acta Cryst. e, 70, pp. o1020-o102
Crystal Structure Of (3e)-3-[(4-nitrophenoxy) Methyl]-4-phenylbut-3-en-2-one
Get PDFIn the title compound, C17H15NO4, the conformation about the C=C double bond [1.348(2)Å] is E with the ketone group almost co-planar [C-C-C-C torsion angle = 7.2(2)°] but the phenyl group twisted away [C-C-C-C = 160.93(17)°]. The terminal aromatic rings are almost perpendicular to each other [dihedral angle = 81.61(9)°] giving the molecule an overall U-shape. The crystal packing feature benzene-C-H⋯O(ketone) contacts that lead to supramolecular helical chains along the b axis. These are connected by π-π interactions between benzene and phenyl rings [inter-centroid distance = 3.6648(14)Å], resulting in the formation of a supramolecular layer in the bc plane.709o1020o1021Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.L., Giacovazzo, C., Guagliardi, A., Moliterni, A.G.G., Spagna, R., (1999) J. Appl. Cryst32, pp. 115-119Brandenburg, K., (2006) DIAMOND, , Crystal Impact GbR, Bonn, Germany(2009) APEX2 and SAINT, , Bruker Bruker AXS Inc., Madison, Wisconsin, USA(2010) Marvinsketch, , http://www.chemaxon.com, ChemaxonFarrugia, L.J., (2012) J. Appl. Cryst45, pp. 849-854De Paula, B.R.S., Zampieri, D.S., Rodrigues, J.A.R., Moran, P.J.S., (2013) Tetrahedron: Asymmetry24, pp. 973-981Rodrigues, J.A.R., Moran, P.J.S., Conceicaõ, G.J.A., Fardelone, L.C., (2004) Food Technol. Biotechnol42, pp. 295-303Sheldrick, G.M., (1996) SADABS, , University of Göttingen, GermanySheldrick, G.M., (2008) Acta Cryst A64, pp. 112-122Westrip, S.P., (2010) J. Appl. Cryst43, pp. 920-92
- …
