Abstract
The ability of the enzymes that are present in micro-organisms to catalyse chemical reactions has been known for thousands of years; indeed the fermentation of sugars into alcohol using yeast is described in the early scriptures.1
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References
For an interesting historical review see M.K. Turner in ‘The Chemical Industry’ (ed. C.A. Heaton), Blackie, Glasgow and London, 1986, p. 284.
For full reviews see J.B. Jones, Tetrahedron,1986, 42,3351 and references therein.
R.A. Johnson, ‘Oxygenations with Micro-organisms’ in ‘Oxidation in Organic Chemistry’ ed. W.S. Trahanovsky, Academic Press, New York, 1978, Volume C; W. Charney and H.L. Herzog, ‘Microbial Transformations of Steroids’, Academic Press, New York, 1967, p. 26.
S. Butt and S.M. Roberts, Nat. Prod. Reports, 1986, 3, 489.
B. Wipf, E. Kupfer, R. Bertazzi, and H.G.W. Leuenberger, Hely. Chim. Acta, 1983, 66, 485; see also J. Ehrler, F. Giovannini, B. Lamatsch, and D. Seebach, Chimia, 1986, 40, 172.
K. Mori and H. Watanabe, Tetrahedron,1981, 37,1341; idem. ibid,1986, 42,295. Professor Mori has synthesized a wide range of natural products from optically active 3-hydroxyalkanoates.
D. Seebach and M. Eberle, Synthesis, 1986, 37.
C. Fuganti, P. Grasselli, P. Casati, and M. Carmeno, Tetrahedron Letters, 1985, 26, 101; W.-R. Shieh, A.S. Gopalan, and C.J. Sih, J. Am. Chem. Soc., 1985, 107, 2993.
C.J. Sih and C.-S. Chen, Ang. Chem. Int. Ed. Engl., 1984, 23, 570.
P. De Shong, M.-T. Lin, and J.J. Ferez, Tetrahedron Letters, 1986, 27, 2091.
K. Nakamura, T. Miyai, K. Nozaki, K. Ushio, S. Oka, and A. Ohno, Tetrahedron Letters, 1986, 27, 3155.
K. Nakamura, M. Higaki, K. Ushio, S. Oka, and A. Ohno, Tetrahedron Letters, 1985, 26, 4213.
D. Seebach, M.F. Züger, F. Giovannini, B. Sonnleitner, and A. Fiechter, Angew. Chem. Int. Ed. Engl., 1984, 23, 151.
D. Buisson and R. Azerad, Tetrahedron Letters, 1986, 27, 2631.
e.g. the Noyori Reagents, see R. Noyori, T. Ohkuma, M. Kitamura, H. Takaya, N. Sayo, H. Kumobayashi and S. Akutagawa, J. Am. Chem. Soc., 1987, 109, 5856.
H. Suemune, N. Hayashi, K. Funakoshi, H. Akita, T. Oishi, and K. Sakai, Chem. Pharm. Bull., 1985, 33, 2168.
G. Guanti, L. Barfi, and E. Narisano, Tetrahedron Letters, 1986, 27, 3547; T. Fujisawa, E. Kojima, T. Itoh, and T. Sato, Chem. Letters, 1985, 1751; Y. Takaishi, Y.-L. Yang, D.D. Tullio, and C.J. Sih, Tetrahedron Letters, 1982, 23, 5489.
C.-Q. Han, D. Di Tullio, Y.-F. Wang, and C.J. Sih, J. Org. Chem., 1986, 51, 1253.
M. Utaka, H. Watabu, and A. Takeda, Chem. Letters, 1985, 1475.
S. Tsuboi, E. Nishiyama, M. Utaka, and A. Takeda, Tetrahedron Letters, 1986, 27, 1915.
T. Fujisawa, E. Kojima, T. Itoh, and T. Sato, Tetrahedron Letters, 1985, 26, 6089.
D. Buisson, S. El Baba, and R. Azerad, Tetrahedron Letters, 1986, 27, 4453.
W.M. Dai and W.-S. Zhou, Tetrahedron, 1985, 41, 4475; see also D.W. Brooks, H. Mazdiyarni, and P.G. Grothaus, J. Org. Chem., 1987, 52, 3223.
see, for example, C. Fuganti, P. Grasselli, P. Casati, and M. Carmeno, Tetrahedron Letters, 1985, 26, 101.
R. Bowen and S.Y.R. Pugh, Chem. Ind. (London), 1985, 10, 323.
J. Leaver, T.C.C. Gartenmann, S.M. Roberts, and M.K. Turner in ‘Biocatalysis in Organic Media’ (eds. C. Laane, J. Tramper, and M.D. Lilley), Elsevier, Amsterdam, 1987, 411.
J.B. Jones in ‘Enzymes in Organic Synthesis’ (eds. R. Porter and S. Clark), Ciba Foundation Symposium 111, Pitman, 1985, p. 3.
E. Keinar, E.F. Hafeli, K.K. Seth and R. Laned, J. Am. Chem. Soc., 1986, -, 162; for an example of a reduction using growing T. brockii see A. Belan, J. Bolte, A. Fauve, J.G. Gourcy and H. Veschambre, J. Org. Chem., 1987, 52, 256.
S. Butt, H.G. Davies, M. J. Dawson, G.C. Lawrence, J. Leaver, S.M. Roberts, M.K. Turner, B.J. Wakefield, W.F. Wall, and J.A. Winders, Tetrahedron Letters, 1985, 26, 5077; S.M. Roberts, Chem. and Ind., 1988, 384.
L.G. Lee and G.M. Whitesides, J. Org. Chem., 1986, 51, 25.
B. Rambeck and H. Simon, Angew. Chem. Int. Ed. Engl., 1974, 13, 609.
H.G.W. Leuenberger, W. Boguth, E. Widner, and R. Zell, Hely. Chim. Acta, 1979, 62, 455; H. Simon, H. Gunther, J. Bader, and W. Tischer, Angew. Chem. Int. Ed. Engl., 1981, 20, 861; for a recent example of a bakers’ yeast reduction of an a,ß-unsaturated aldehyde see Tetrahedron Letters, 1988, 29, 2197.
M. Utaka, S. Konishi, and A. Takeda, Tetrahedron Letters, 1986, 27, 4737.
P. Gramatica, P. Manitto, D. Monti, and G. Speranza, Tetrahedron, 1986, 42, 6687; see also P. Gramatica, G. Speranza, P. Manitto, and D. Monti, ibid, 1987, 43, 4481.
K.P. Lok, I.J. Jakovac, and J.B. Jones, J. Am. Chem. Soc., 1985, 107, 2521; see also G.L. Lemiére, J.A. Lepoivre and F.C. Alderweireldt, Tetrahedron Letters, 1985, 26, 4527; the difficulties in recycling NAD(P)+ have been discussed, L.G. Lee and G.M. Whitesides, ibid, 1985, 107, 6999.
Y. Khandelwal, N.J. de Souza, S. Chatterjee, B.N. Ganguli, and R.H. Rupp, Tetrahedron Letters, 1987, 28, 4089.
J.-D. Fourneron, A. Archelas, B. Vigne, and R. Furstoss, Tetrahedron, 1987, 43, 2273; V. Lamare, J.D. Fourneron, R. Furstoss, C. Ehret, and B. Corbier, Tetrahedron Letters, 1987, 28, 6269.
Y. Yamazaki and H. Maeda, Tetrahedron Letters, 1985, 26, 4775.
C.J. Francis and J.B. Jones, J. Chem. Soc., Chem. Commun., 1984, 579; L.K.P. Lau, R.A.H.F. Hui, and J.B. Jones, J. Org. Chem., 1986, 51, 2047.
F. Björkling, J. Boutelje, S. Gatenbeck, K. Hult, T. Norin, and P. Szmulik, Tetrahedron, 1985, 41, 1347; F. Björkling, J. Boutelje, S. Gatenbeck, K. Hult, and T. Norin, Tetrahedron Letters, 1985, 26, 4957.
M. Kurihara, K. Kamiyama, S. Kobayashi, and M. Ohno, Tetrahedron Letters, 1985, 26, 5831.
G. Sabbioni and J.B. Jones, J. Org. Chem., 1987, 52, 4565.
H.-J. Gais and K.L. Lukas, Angew. Chem. Int. Ed. Engl., 1984, 23, 142.
B.I. Glanzer, K. Faber, and H. Griengl, Tetrahedron, 1987, 43, 771.
A.J.H. Klunder, F.J.C. van Gastel, and B. Zwanenburg, Tetrahedron Letters, 1988, 29, 2697.
H. Hemmerle and H.-J. Gais, Tetrahedron Letters, 1987, 28, 3471.
B.I. Glanzer, K. Faber, and H. Griengl, Tetrahedron, 1987, 43, 5791.
C. Chan, P.B. Cox, and S.M. Roberts, J. Chem. Soc., Chem. Corrunun.,1988
I.C. Cotterill, H. Finch, D.P. Reynolds, S.M. Roberts, H.S. Rzepa, K.M. Short, A.M.Z. Slawin, C.J. Wallis, and D.J. Williams, J. Chem. Soc., Chem. Commun., 1988, 470.
G. Eichberger, G. Penn, K. Faber, and H. Griengl, Tetrahedron Letters, 1986, 27, 2843.
D.R. Deardorff, A.J. Matthews, D.S. McMeekin, and C.L. Craney, Tetrahedron Letters, 1986, 27, 1255.
In addition trifluoroethanol reacts selectively with various a,ß-unsaturated ketones and esters to give the y-hydroxyl carbonyl compounds, T. Kitazume and N. Ishikawa, Chem. Letters, 1984, 1815.
G. Kirchner, M.P. Scollar, and A.M. Klibanov, J. Am. Chem. Soc., 1985, 107, 7072.
P.E. Sonnet, J. Org. Chem., 1987, 51, 3477.
G.M. Ramos Tombo, H.-P. Schdr, X. Fernandex, and O. Ghisalba, Tetrahedron Letters, 1986, 27, 5707.
T.A. Savage in ‘Biotechnology of Industrial Antibiotics’, ed. E.J. Vandamme, Marcel Dekker, New York, 1984, p. 171.
I. Chibata in ‘Asymmetric Reactions and Processes in Chemistry’ (eds. E.L. Eliel and S. Otsuka), Am. Chem. Soc., Washington, 1982; see also C. Wandrey in ‘Enzymes as Catalysts in Organic Synthesis’ (ed. M. Schneider), D. Reidel, Dordrecht, 1986, p. 263.
H. Yamada in ‘Enzyme Engineering’ (eds. I. Chibata, S. Fukui, and L.B. Wingard), Vol. 6, Plenum Press, New York, 1982, p. 97; T. Fukumura, Agric. Biot. Chem., 1976, 40, 1687, 1695; idem, ibid, 1977, 41, 1327.
C.F. Barbas III and C.-H. Wong, Tetrahedron Letters, 1988, 29, 2907; E.K. Bratovanova, I.B. Stoineva, and D.D. Petkov, Tetrahedron, 1988, 44, 3633; A. A. Ferjancic, A. Puigserver, and H. Gaertner, Biotech. Letters, 1988, 10, 101.
M.-J. de Smet, B. Witholt, and H. Wynberg, J. Org. Chem., 1981, 46, 3128; A.G. Katopodis, K. Wimalasena, J. Lee, and S.W. May, J. Am. Chem. Soc., 1984, 106, 7928.
C.-H. Wong and G.M. Whitesides, J. Org. Chem., 1983, 48, 3199; J.R. Durrwachter, D.G. Drueckhammer, K. Nozaki, H.M. Swears, and C.-H. Wong, J. Am. Chem. Soc., 1986, 108, 7812.
C. Fuganti, P. Grasselli, and S. Servi, J. Chem. Soc., Perkin Trans. I, 1983, 241; C. Fuganti, P. Grasselli, S. Servi, F. Spreafico, and C. Zirolfi, J. Org. Chem., 1984, 49, 4087.
E. Hochuli, Rely. Chim. Acta, 1983, 66, 489; L. Jaenicke and J. Preun, Eur. J. Biochem., 1984, 138, 319.
Y. Vo-Quang, D. Marais, L. Vo-Quang, F. Le Gaffic, A. Thiery, M. Maestracci, A. Arnaud, and P. Galzy, Tetrahedron Letters, 1987, 28, 4057.
D.C. Crans and G.M. Whitesides, J. Am. Chem. Soc., 1985, 107, 7008, 7019.
S. Shuto, S. Ueda, S. Imamura, K. Fukukawa, A. Matsuda, and T. Ueda, Tetrahedron Letters, 1987, 28, 199.
H. Ohta, Y. Okamoto, and G. Tsuchihashi, Chem. Letters, 1984, 205; H.L. Holland, H. Popperl, R.W. Ninniss, and P.C. Chenchaiah, Can. J. Chem., 1985, 63, 1118.
M.A. Findeis and G.M. Whitesides, J. Org. Chem., 1987, 52, 2838.
S.V. Ley, F. Sternfeld, and S.C. Taylor, Tetrahedron Letters, 1987, 28, 225.
S.J.C. Taylor, D.W. Ribbons, A.M.Z. Slawin, D.A. Widdowson, and D.J. Williams, Tetrahedron Letters, 1987, 28, 6391.
A.R. Clarke, C.J. Smith, K.W. Hart, H.W. Wilks, W.N. Chia, T.V. Lee, J.J. Birktoft, L.J. Banaszak, B.A. Barstow, T. Atkinson, and J.J. Holbrook, Biochem. Biophys. Res. Commun., 1987, 148, 15.
A.D. Napper, S.J. Benkovic, A. Tramontano, and R.A. Lerner, Science, 1987, 237, 1041.
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Roberts, S.M. (1989). Enzymes as Catalysts in Organic Synthesis. In: Cooper, A., Houben, J.L., Chien, L.C. (eds) The Enzyme Catalysis Process. Progress in Mathematics. Springer, Boston, MA. https://doi.org/10.1007/978-1-4757-1607-8_29
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