Abstract
The bioreductions mediated by BY and other microorganisms are considered mainly from a preparative point of view. The use of other microorganisms is reported when BY is either unable to perform the reaction or if this proceeds with moderate enantioselectivity or when the opposite stereochemical outcome of the reaction should be obtained. The biotransformation of nitrogen-containing groups is especially addressed. The bioreductions of trinitrotoluene is presented as an example of the bioremediation of explosives.
This is a preview of subscription content, log in via an institution.
Buying options
Tax calculation will be finalised at checkout
Purchases are for personal use only
Learn about institutional subscriptionsPreview
Unable to display preview. Download preview PDF.
References
S. Servi, Ed. (1992) Microbial Reagents in Organic Synthesis, Kluwer Academic Publishers, Dordrecht.
Holland, H.L. (1998) Microbial trasformations, Current Opinion in Chemical Biology 2 77–84.
. Servi, S. (1990) Baker’s yeast as a reagent in organic synthesis, Synthesis 1–25.
Csuk, R. and Glänzer, B.I. (1991) Baker’s yeast mediated transformations in organic chemistry, Chem. Rev. 91 4997.
D’Arrigo, P., Pedrocchi-Fantoni, G. and Servi, S. (1997) Old and new synthetic capacities of baker’s yeast, Adv. Appl. Microbiol. 44 81–123.
Pereira, R.S. (1998) The use of baker’s yeast in the generation of asymmetric centers to produce chiral drugs and other compounds, Crit. Rev. Biotechnol. 18 25–83.
Kometani,T., Yoshii, H. and Matsuno, R. (1996) Large-scale production of chiral alcohols with bakers’ yeast, J. Mol. Catal. B: Enzym. 1, 45–52.
Santaniello, E., Ferraboschi, P., Grisenti, P. and Manzocchi, A. (1992) The biocatalytic approach to the preparation of enantiomerically pure chiral building blocks, Chem. Rev. 92 1071–1140.
Takeshita, M., Yaguchi, R. and Unuma, Y. (1995) Enzymatic synthesis of (1R, 2S)- and (1S, 2R)-2methyl-2,3-epoxy-1-phenylpropanols, Heterocycles 40967–974.
Ferraboschi, P., Casati, S. and Santaniello, E. (1994) Baker’s yeast-mediated hydrogenation of 2-substituted allyl alcohols: a biocatalytic route to a new highly enantioselective synthesis of (R)-2-methyl alkanols, Tetrahedron: Asymmetry 5 19–20.
Fenaboschi, P., Reza Elahi, S., Verza, E., Meroni Rivolta, F. and Santaniello, E. (1996) Baker’s yeast mediated biohydrogenation of 2-substituted allyl alcohols: synthesis of enantiomerically pure (2S)-3benzyloxy-2-methyl-1-propanol, Synlett 1176–1178.
Levene, P.A. and Walti, A. (1943) 1-Propylene glycol, Organic Syntheses Coll. Vol. II, 545–547.
Seebach, D., Sutter, M.A., Weber, R.H. and Züger, M.F. (1985) Yeast reduction of ethyl acetoacetate: (S)-(+)-ethyl 3-hydroxybutanoate, Organic Syntheses 63 1–9.
Mori, K. and Mori, H. (1990) Yeast reduction of 2,2-dimethylcyclohexane-1,3-dione: (S)- (+)-3-hydroxy-2,2dimethylcyclohexanone, ibid. 68 56–63.
Prelog, V. (1964) Specification of the stereospecificity of some oxidoreductases by diamond lattice sections, Pure Appl. Chem. 9 119–130.
Ward, O.P. and Young, C.S. (1990) Reductive biotransformations of organic compounds by cells or enzymes of yeast, Enzyme Microb. Technol. 12 482–493.
Nakamura, K. (1992) Stereochemical control in microbial reduction, in S. Servi (ed.); Microbial Reagents in Organic Synthesis, Kluwer Academic Publishers, Dordrecht, pp.388–398.
Nakamura, K., Ushio, K., Oka, S. and Ohno, A. (1984) Stereochemical control in yeast reduction, Tetrahedron Lett. 25 3979–3982.
Neuberg, C. and Nord, F.F. (1919) Die phytochemische reduktion der ketone. Biochemische darstellung optisch-aktiver sekundärer alkohole, Ber. 52 2237–2248.
Fogagnolo, M. Giovannini, P.P., Guerrini, A., Medici, A., Pedrini, P. and Colombi, N. (1998) Homochiral (R)- and (S)-1-heteroaryl-and 1-aryl-2-propanols via microbial redox, Tetrahedron: Asymmetry 9 2317–2327.
Fantin, G., Fogagnolo, M., Giovannini, P.P., Medici, A., Pedrini, P., Gardini, F. and Lanciotti, R. (1996) Anti-Prelog microbial reduction of prochiral carbonyl compounds, Tetrahedron 52 3547–3552.
Rykowsky, A., Lipinska, T., Guzik, E., Adamiuk, M. and Olender, E. (1997) 1,2,4 — Triazines in organic synthesis. 6. Enantioselective reduction of 5-acy1–1,2,4-triazines and their oximes by baker’s yeastPol. J. Chem. 71 69–76.
Takemoto, M. and Achiwa, K. (1994) Synthesis of optically active a-phenylpyridylmethanols with baker’s yeast, Chem. Pharm. Bull. 42 802–805.
Huber, P., Bratovanov, S., Bienz, S., Syldatk, C. and Pietzsch, M. (1996) Chiral silicon groups as auxiliaries for enantioselective synthesis: access to optically active silanes by biotransformation and the enantiospecific preparation of (R)-(+)-1-phenylethanol, Tetrahedron: Asymmetry 7, 69–78.
Maguire, A.R. and Lowney, D.G. (1997) Asymmetric reduction of 1-methylsulfonylalkan-2-ones with baker’s yeast, J. Chem. Soc.Perkin I, 235–238.
Dao, D.H., Okamura, M., Akasaka, T., Kawai, Y., Hida, K. and Ohno, A. (1998) Stereochemical control in microbial reduction. Part 31: reduction of alkyl 2-oxo-4-arylbutyrates by baker’s yeast under selected reaction conditions, Tetrahedron: Asymmetry 9 2725–2737.
Eh, M. and Kalesse, M. (1995) Remarkable kinetic resolution of chiral 13-keto esters by baker’s yeast reduction, Synlett, 837–838.
Quir¨®s, M., Rebolledo, F., Liz, R. and Gotor, V. (1997) Enantioselective reduction of (3-keto amides by the fungus Mortierella isabellinaTetrahedron: Asymmetry 8 3035–3038.
Quir¨®s, M., Rebolledo, F. and Gotor, V. (1999) Bioreduction of 2-oxocyclopentanecarboxamides: syntheses of optically active 2-aminomethyl-and 2-aminocyclopentanols, Tetrahedron: Asymmetry 10 473–486.
Ferraboschi, P., Santaniello, E., Tingoli, M., Aragozzini, F. and Molinari, F. (1993) Microbial reduction of 2-keto acetals as a biocatalytic approach to the enantioselective synthesis of optically active 2-hydroxy acetals, Tetrahedron: Asymmetry 4 1931–1940.
Tanikaga, R., Obata, Y. and Kawamoto, K.-i. (1997) Baker’s yeast mediated reduction of cyclohexanones containing a nitro or a sulfonyl group at C-3, Tetrahedron: Asymmetry 8 3101–3106.
Danchet, S., Bigot, C., Buisson, D. and Azerad, R. (1997) Dynamic kinetic resolution in the microbial reduction of a-monosubstituted 3-oxoesters: the reduction of 2-carbethoxy-cycloheptanone and 2carbethoxy-cyclooctanone, Tetrahedron: Asymmetry 8 1735–1739.
Fantin, G., Fogagnolo, M., Medici, A., Pedrini, P., Marotta, E., Monti, M and Righi, P. (1996) Microbial reduction of methyl-substituted bicyclo[3.2.0]hept-3-en-6-ones: a screening to homochiral endo-and exo-alcohols, Tetrahedron: Asymmetry 7, 277–282.
Satoh, K., Imura, A., Miyadera, A., Kanai, K. and Yukimoto, Y. (1998) An efficient synthesis of a key intermediate of DU-6859a via asymmetric microbial reduction, Chem. Pharm. Bull. 46 587–590.
Kometani, T. Sakai, Y., Matsumae, H. Shibatani, T. and Matsuno, R. (1997) Production of (2S,3S)2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(511)-one, a key intermediate for Diltiazem synthesis, by bakers’ yeast-mediated reduction, J. Ferment. Bioeng. 84 195–199.
Das, B., Madhusudhan, P. and Kashinatham, A. (1998) The first conversion of camptothecin to (S)mappicine by an efficient chemoenzymatic method, Bioorg. Med. Chem. Lett. 8 1403–1406.
Boutoute, P., Mousset, G. and Veschambre, H. (1998) Regioselective or enantiogenic electrochemical and microbial reductions of 1,2-diketones, New J. Chem.,247–251.
Nakamura, K.,Kondo, S.-i., Kawai, Y., Hida, K., Kitano, K. and Ohno, A. (1996) Enantio-and regioselective-reduction of a-diketones by baker’s yeast, Tetrahedron: Asymmetry 7, 409–412.
Crocq, V., Masson, C., Winter,J., Richard, C., Lemaitre, G., Lenay, J., Vivat, M., Buendia, J, and Prat, D. (1997) Synthesis of Trimegestone: the first industrial application of bakers’ yeast mediated reduction of a ketone, Org. Process. Res. Dev. 1 2–13.
Fauve, A., Veschambre, H. (1988) Microbiological reduction of acyclic (3-diketones, J. Org . Chem. 53, 5215–5219.
Matsumura, S., Kawai, Y., Takahashi, Y. and Toshima, K. (1994) Microbial production of (2R,4R)-2,4-pentanediol by enantioselective reduction of acetylacetone and stereoinversion of 2,4-pentanediol, Biotechnol. Lett. 16, 485–490.
Ikeda, H., Sato, E., Sugai, T. and Ohta, H. (1996) Yeast-mediated synthesis of optically-active diols with C-2-symmetry and (R)-4-pentanolide, Tetrahedron 52, 8113–8127.
Otten, S., Fröhlich, R. and Haufe, G. (1998) Synthesis and structural characterization of enantiopure (2R,5R)-(+)-2,5-dimethylthiolane, Tetrahedron: Asymmetry 9, 189–191.
Uchiyama, M., Katoh, N., Mimura, R., Yokota, N., Shimogaichi, Y., Shimazaki, M. and Ohta, A. (1997) Highly enantioselective reduction of symmetrical diacetylaromatics with baker’s yeastTetrahedron: Asymmetry 8, 3467–3474.
Zhou, B.-n., Gopalan, A.S., VanMiddlesworth, F., Shieh, W.-R. and Sih, C.J. (1983) Stereochemical control of yeast reductions. 1. Asymmetric synthesis of L-camitine, J. Am. Chem. Soc. 105, 5925–5926.
Aragozzini, F., Valenti, M., Santaniello, E., Ferraboschi, P. and Grisenti, P. (1992) Biocatalytic enantioselective preparations of (R)- and (S)- ethyl 4-chloro-3-hydroxybutanoate, a useful chiral synthon, Biocatalysis 5, 325–332.
Manzocchi, A., Fiecchi, A. and Santaniello, E. (1987) Stereochemically controlled bakers’-yeastmediated reductions: synthesis of (S)-(+)-1,2-propanediol and (S)-(—)-1,3-butanediol, 1-benzyl ethers, Synthesis, 1007–1009.
Manzocchi, A., Fiecchi, A. and Santaniello, E. (1988) Stereochemical control of bakers’ yeast mediated reduction of a protected 2-hydroxy ketone, J. Org . Chem. 53, 4405–4407.
Ferraboschi, P., Grisenti, P., Manzocchi, A. and Santaniello, E. (1994) Baker’s yeast-mediated reduction of a-hydroxy ketones and derivatives: the steric course of the biotransformation, Tetrahedron 35,10539–10548.
Utaka, M., Ito, H., Mizumoto, T. and Tsuboi, S. (1995) Regio-and enantioselective synthesis of (S)-1-acetoxy-2-hydroxy-4-alkanones by use of bakers’ yeast reduction of 1-acetoxy-2,4-alkanediones, Tetrahedron: Asymmetry 6, 685–686.
Egri, G., Kolbert, A., Bàlint, J., Fogassy, E., Novàk, L. and Poppe, L. (1998) Baker’s yeast mediated stereoselective biotransformation of 1-acexy-3- aryloxypropan-2-ones, ibid. 9,271–283.
Dumas, M. (1874) Recherches sur la fermentation alcoolique Ann. Chim. Phys. 3, 59–108.
Neuberg, C. and Nord, F. F. (1914) Phytochemische Bildung von Äthylmercaptan, Chem. Ber. 47, 2264–2271.
Nielsen, J. K. and Madsen, J. 0. (1994) Stereoselective reduction of thiocarbonyl compounds with baker’s yeast, Tetrahedron: Asymmetry 5, 403–410.
Abo, M., Okubo, A. and Yamazaki, S. (1997) Preparative asymmetric deoxygenation of alkyl aryl sulfoxides by Rhodobacter sphaeroides f.sp. denitrificansTetrahedron: Asymmetry 8, 345–348.
Hanlon, S. P., Graham, D. L, Hogan, P. J., Holt, R. A., Reeve, C. V., Shaw, A. L., McEwan, A. G. (1998) Asymmetric reduction of racemic sulfoxides by dimethyl sulfoxide reductases from Rhodobacter capsulatusEscherichia coli and Proteus species, Microbiology 144 2247–2253.
Baruah, M., Boruah, A., Prajapati, D. and Sandhu, J.S. (1996) Bakers’ yeast mediated chemoselective reduction of azidoarenes, Synlett 1193–1194.
Besse, P., Veschambre, H., Chênevert, R., Dickman, M. (1994) Chemoenzymatic synthesis of chiral 0azidoalcohols. Application to the preparation of chiral aziridines and aminoalcohols, Tetrahedron: Asymmetry 5, 1727–1744.
Kamal, A., Damayanthi, Y., Reddy, B.S.N., Lakminarayana, B. and Reddy, B.S.P. (1997) Novel biocatalytic reduction of aryl azides: chemoenzymatic synthesis of pyrrolo[2,1-c][1,4]benzodiazepine antibiotics, Chem. Commun., 1015–1516.
Kamal, A., Laxminarayana, B. and Gayarti,N.L. (1997) Stereo and chemoselective enzymatic reduction of azido functionality: synthesis of 4-ß-aminopodophyllotoxin congeners by baker’s yeast, Tetrahedron Lett. 38 6871–6874.
Neuberg, C. and Welde, E. (1914) Phytochemical reductions. II. Transformation of aliphatic nitro compounds into amino compounds, Biochem. Z. 60 470–476.
Takeshita, M., Yoshida, S., Kiya, R., Higuchi, N. and Kobayashi, Y. (1989) Reduction of aromatic nitro compounds with baker’s yeast, Chem. Pharm. Bull. 37 615–617.
Blackie, J.A., Turner, N.J. and Wells, A.S. (1997) Concerning the baker’s yeast (Saccharomyces cerevisiae) mediated reduction of nitroarenes and other N-O containing functional groups, Tetrahedron Lett. 38 3043–3046
Easton, C.J., Huges, M.M., Tiekink, E.R.T., Savage, G.P. and Simpson, G.W. (1995) Aryl nitrile oxide cycloaddition reactions in the presence of baker’s yeast and a-cyclodextrin, Tetrahedron Lett. 36 629–632.
Davey, C.L., Powell, L.W., Turner, N.J. and Wells, A. (1994) Regioselective reduction of substituted dinitroarenes using baker’s yeastTetrahedron Lett. 35 7867–7870.
Spain, J.C. (1995) Biodegradation of nitroaromatic compounds, Ann. Rev. Microbiol. 49 523–555.
Kalafut, T., Wales, M.E., Raspogi, V.K., Naumova, R.P., Zaripova, S.K. and Wild, J.R. (1998) Biotranformation patterns of 2,4,6-trinitrotoluene by aerobic bacteriaCurr. Microbiol. 36 45–54.
Navarro-Ocaña, A., Jim nez-Estrada, M., Gonzàlez-Paredes, M.B. and Bàrzana, E. (1996) Synthesis of substituted isoxazoles from (Z)-3-alkyl-3-nitro-2-phenylpropenenitriles using baker’s yeast, Synlett 695–696.
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2000 Springer Science+Business Media Dordrecht
About this chapter
Cite this chapter
Santaniello, E., Ferraboschi, P., Manzocchi, A. (2000). Recent Advances on Bioreductions Mediated by Baker’s Yeast and Other Microorganisms. In: Zwanenburg, B., Mikołajczyk, M., Kiełbasiński, P. (eds) Enzymes in Action. NATO Science Partnership Sub-Series: 1:, vol 33. Springer, Dordrecht. https://doi.org/10.1007/978-94-010-0924-9_5
Download citation
DOI: https://doi.org/10.1007/978-94-010-0924-9_5
Publisher Name: Springer, Dordrecht
Print ISBN: 978-0-7923-6696-6
Online ISBN: 978-94-010-0924-9
eBook Packages: Springer Book Archive