Abstract
The stereospecificity of biomolecules is a characteristic feature of the molecular logic of living cells. Chiral natural products are usually present in only one of their possible chiral forms. Also, the configuration of molecules (natural or unnatural) is very important in their biological function. Asymmetric synthesis is a primary focus of activity in organic chemistry and enzymes offer a convenient alternative to conventional reagents as a means of expressing chirality in a synthetic scheme. We report here the chemoenzymatic synthesis (or approach) of natural products and bioactive compounds such as baclofen and fluoxetine (pharmaceuticals), amidinomycin and chloramphenicol (antibiotics), piperidine alkaloids, phospholipids and vitamin E.
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References
Wainer, I.W., Drayer, D.E. (eds.), (1988) Drug Stereochemistry, Dekker, New York.
Crosby, J. (1991) ‘Synthesis of optically active compounds: a large scale perspective’, Tetrahedron 47, 4789–4846.
Ramos Tombo, G.M., Bellus, D. (1991) ‘Chirality and crop protection’, Angew. Chem. Int. Ed. Engl. 30, 1193–1215.
Hanessian, S. (1983) Total Synthesis of Natural Products: The ‘Chiron’ Approach, Pergamon Press, Oxford.
Ito, A., Takahashi, R. Baba, Y. (1975) ‘Synthesis of pumiliotoxin 251D from proline’, Chem. Pharm. Bull. 23, 3081–3086.
Coppola, G.M., Schuster, H.F. (1983) Asymmetric Synthesis: construction of chiral molecules using amino acids, Wiley-Interscience, New York.
Morrison, J.D. (ed.), (1983–1985) Asymmetric Synthesis, Vol. 1–5, Academic Press, New York.
Enders, D., Schubert, H. (1984) ‘Enantioselective synthesis of β-substituted primary amines; α-alkylation/reduction animation of aldehydes via SAMP-hydrazones’, Angew. Chem. Int. Ed. Engl. 23, 365–366.
Corey, E.J., Bakshi, R.K., Shibata, S., Chen, C.P., Singh, V.K. (1987) ‘A stable and easily prepared catalyst for the enantioselective reduction of ketones. Applications to multistep synthesis’, J. Am. Chem. Soc. 109, 7925–7926.
Davies, H.G., Green, R.H., Kelly, D.R., Roberts, S.M. (eds.), (1989) Biotransformations in Preparative Organic Chemistry, Academic Press, London.
Klibanov, A.M. (1990) ‘Asymmetric transformations catalyzed by enzymes in organic solvents’, Acc. Chem. Res. 23, 114–120.
Chênevert, R., Létourneau, M., Thiboutot, S. (1990) ‘Resolution of β-hydroxy-α-amino acids by the action of proteases on their N-acyl methyl esters, Can. J. Chem. 68, 960–963.
Chênevert, R., Thiboutot, S. (1989) ‘Synthesis of chloramphenicol via an enzymatic enantioselective hydrolysis’, Synthesis, 444–446.
Clark, J.E., Fisher, P.A., Schumacher, D.P. (1991) ‘An enzymatic route to florfenicol’, Synthesis, 891–894.
Giordano, C, Cavicchioli, S., Levi, S., Villa, M. (1991) ‘Direct conversion of (1S, 2S)-2-Amino-l-[(4-methylthio)phenyl]-1,3-propanediol into its enantiomer for efficient synthesis of thiamphenicol and florfenicol’, J. Org. Chem. 56, 6114–6118.
Fonza, G., Fuganti, C, Grasseli, P., Mele, A. (1991) ‘On the mode of bakers’ yeast transformation of 3-chloropropiophenone and related ketones. Synthesis of (2S)-[2-D]propiophenone, (R)-fluoxetine, and (R)- and (S)-fenfluramine’, J. Org. Chem. 56, 6019–6023.
Chênevert, R., Fortier, G. (1991) ‘Chemoenzymatic synthesis of both enantiomers of fluoxetine’, Chem. Lett., 1603–1606.
Buisson, D., Azerad, R., Sanner, C, Larchevêque, M. (1991) ‘Stereocontrolled reduction of β-ketoesters by Geotricum candidum. Preparation of D-3-hydroxyalkanoates’, Tetrahedron Asymmetry 2, 987–988.
Chênevert, R., Desjardins, M. (1991) ‘Chemoenzymatic synthesis of both enantiomers of baclofen’, Tetrahedron Lett., 32, 4249–4250.
Guanti, G., Podgorski, T., Thea, S., Williams, A. (1990) ‘Enzyme catalyzed monohydrolysis of 2-aryl-l,3-propanediol diacetates. A study of structural effects of the aryl moiety on the enantioselectivity’, Tetrahedron 46, 7081–7092.
Drueckhammer, D.G., Hennen, W.J., Pederson, R.L. Barbas, C.F., Gautheron, C.M., Krach, T., Wong, C.H. (1991) ‘Enzyme catalysis in synthetic carbohydrate chemistry’, Synthesis, 499–525.
Fuganti, C., Grasselli, P. (1982) ‘Synthesis of the C14 chromanyl moiety of natural α-tocopherol (Vitamin E)’, J. Chem. Soc. Chem. Commun., 205–206.
Gramatica, P., Manitto, P., Monti, D., Speranza, G. (1986) ‘New syntheses of optically active vitamin E side chain by chemicoenzymatic approach’, Tetrahedron 42, 6687–6692.
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© 1992 Springer Science+Business Media Dordrecht
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Chênevert, R. et al. (1992). Chemoenzymatic Synthesis of Natural Products and Bioactive Compounds. In: Servi, S. (eds) Microbial Reagents in Organic Synthesis. NATO ASI Series, vol 381. Springer, Dordrecht. https://doi.org/10.1007/978-94-011-2444-7_11
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DOI: https://doi.org/10.1007/978-94-011-2444-7_11
Publisher Name: Springer, Dordrecht
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