Biotransformations in organic synthesis

Bioresource Technology

Volumn 74, Issue 1, 2000, Pages 49-62

  Loughlin, Wendy A ^a  

^a GRIFFITH UNIVERSITY   (Australia)

Author keywords

Biotransformation; Enzyme; Organic synthesis

Indexed keywords

HYDROLASE; OXIDOREDUCTASE;

BIOTRANSFORMATION; CATALYST; DRUG SYNTHESIS; ENANTIOMER; ENZYME ACTIVITY; ENZYME IMMOBILIZATION; ENZYME MODIFICATION; HYDROLYSIS; OXIDATION; PRIORITY JOURNAL; RECOMBINANT DNA TECHNOLOGY; REDUCTION; REVIEW; STEREOCHEMISTRY; TECHNIQUE;

EID: 0034110701     PISSN: 09608524     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-8524(99)00145-5     Document Type: Article

References (130)

1. Adam, W., Boland, W., HartmannSchreier, J., Humpf, H.U., Lazarus, M., Saffert, A., Saha-Möller, C.R., Schreier, P., 1998. α-Hydroxylation of carboxylic acids with molecular oxygen catalyzed by the α-oxidase of peas (Pisum sativum), A Novel biocatalytic synthesis of enantiomerically pure (R)-2-hydroxy acids. J. Am. Chem. Soc. 120, 11044-11048.
2. Akakabe, Y., Matsui, K., Kajiwara, T., 1999. Enantioselective α-hydroperoxylation of long chain fatty acids with crude enzyme of marine green alga Ulva pertusa. Tetrahedron Lett. 40, 1137-1140.
3. Akhtar, M.S, Botting, N.B., Cohen, M.A., Gani, D., 1987. Enantio-specific synthesis of 3-substituted aspartic acids via enzymatic amination of substituted fumaric acids. Tetrahedron 43, 5899-5908.
4. Alexandre, F.R., Huet, F., 1998. Asymmetrisation of meso-1,3-diols utilising Pseudomonas fluorescens lipase. Tetrahedron Asymmetry 9, 2301-2310.
5. Andersson, M.A., Allenmark, S.G., 1998. Asymmetric sulfoxidation catalysed by a vanadium bromoperoxidase: Substrate requirements of the catalyst. Tetrahedron 54, 15293-15304.
6. Anzai, J., Kobayashi, Y., Nakamura, N., 1998. Alternate deposition of concanavalin A and mannose labeled enzymes on a solid surface to prepare catalytically active enzyme thin films. J. Chem. Soc., Perkin Trans. II, 461-462.
7. 2: The first biotechnological application of a carboxylase enzyme. Tetrahedron 54, 8841-8846.
8. c) disaccharides with recombinant sialyl-transferase. Bioorg. Med. Chem. Lett. 8, 157-160.
9. Baisch, G., Öhrlein, R., Streiff, M., 1998b. Enzymatic fucosylations of non-natural sialylated type-I trisaccharides with recombinant fucosyl-transferase-III. Bioorg. Med. Chem. Lett. 8, 161-164.
10. Baisch, G., Öhrlein, R., Streiff, M., Kolbinger, F., 1998c. On the preparative use of recombinant β(1-3) galactosyl-transferase. Bioorg. Med. Chem. Lett. 8, 751-754.
11. a-libraries with two nonnatural monosaccharide units. Bioorg. Med. Chem. Lett. 8, 755-758.
12. Baisch, G., Öhrlein, R., Kolbinger, F., Streiff, M., 1998e. On the preparative use of pig α(1-3)galactosyl-transferase. Bioorg. Med. Chem. Lett. 8, 1575-1578.
13. Bakke, M., Takizawa, M., Sugai, T., Ohta, H., 1998. Lipase-catalysed enantiomeric resolution of ceramides. J. Org. Chem. 63, 6929-6938.
14. Bastida, A., Fernández-Lafuente, R., Fernández-Lafuente, G., Guisán, J.M., Pagani, G., Terreni, M., 1999. Regioselective hydrolysis of peracetylated α-D-glucopyranose catalyzed by immobilised lipases in aqueous medium. A facile preparation of useful intermediates for oligosaccharide synthesis.. Bioorg. Med. Chem. Lett. 9, 633-636.
15. Beecher, J., Willets, A., 1998. Biotransformation of organic sulfides. Predictive active site models for sulfoxidation catalysed by 2,5-diketocamphane 1,2-monooxygenase and 3,6-diketocamphane 1,6-monooxygenase, enantiocomplementary enzymes from Pseudomonas putida NCIMB 10007. Tetrahedron Asymmetry 9, 1899-1916.
16. Bianchini, E., Chinaglia, N., Dean, M., Giovannini, P.P., Medici, A., Pedrini, P., Poli, S., 1999. Regiospecific oxidoreductions catalysed by a new Pseudomonaspaucimobilis hydroxysteroid dehydrogenase. Tetrahedron 55, 1391-1398.
17. Bisht, K.S., Gross, R.A., Kaplan, D.L., 1999. Enzyme-mediated regioselective acylations of sophorolipids. J. Org. Chem. 64, 780-789.
18. Bisht, K.S., Deng, F., Gross, R.A, Kaplan, D.L., Swift, G., 1998. Ethyl glucoside as a multifunctional initiator for enzyme-catalysed regioselective lactone ring-opening polymerization. J. Am. Chem. Soc. 120, 1363-1367.
19. Boland, W., Frößl, C., Lorenz, M., 1991. Esterolytic and lipolytic enzymes in organic synthesis. Synthesis, 1049-1072.
20. Botes, A.L., Weijers, C.A.G.M., vanDyk, M.S., 1998. Biocatalytic resolution of 1,2-epoxyoctane using resting cells of different yeast strains with novel epoxide hydrolase activities. Biotech. Lett. 20, 421-426.
21. Boyd, D.R., Sharma, N.D., Haughey, S.A., Kennedy, M.A., McMurray, B.T., Sheldrake, G.N., Allen, C.C.R., Dalton, H., Sproule, K., 1998. Toluene and naphthalene dioxygenase-catalysed sulfoxidation of alkyl aryl sulfides. J. Chem. Soc., Perkin Trans. I, 1929-1933.
22. Brosa, C., Rodriguez-Santamarta, C., Salvá, J., Barberà, E., 1998. Baeyer-Villiger oxidation of Pseudomonas putida NCIMB 10007 in organic solvents, The influence on the regioselectivity. Tetrahedron 54, 5781-5788.
23. Carrea, G., Ottolina, G., Riva, S., 1995. Role of solvents in the control of enzyme selectivity in organic media. Trends Biotechnol. 13, 63-70.
24. Chang, C.S., Tsai, S.W., Lin, C.N., 1998. Enzymatic resolution of (RS)-2-arylpropionic acid thioesters by Candida rugosa lipase catalysed thiotransesterification or hydrolysis on organic solvents. Tetrahedron Asymmetry 9, 2799-2807.
25. Chênevert, R., Goupil, D., Rose, Y.S., Bedard, E., 1998a. Enzymatic desymmetrization of meso cis, cis-2,4,6-disubstituted tetrahydropyrans. Tetrahedron Asymmetry 9, 4285-4288.
26. Chênevert, R., Ngatcha, B.T., Rose, Y.S., Goupil, D., 1998b. Regioand enantioselectivity of the enzyme catalysed hydrolysis of citric acid derivatives. Tetrahedron Asymmetry 9, 4325-4329.
27. Chênevert, R., Rose, Y.S, 1998c. A chemoenzymatic synthesis of both enantiomers of a cis-lignan lactone. Tetrahedron Asymmetry 9, 2827-2831.
28. Cipiciani, A., Cittadini, M., Fringuelli, F., 1998. Improving the enantioselectivity of Candida rugosa lipase in the kinetic resolution of racemic methyl 2-(2,4-dichlorophenoxy) propionate. Tetrahedron 54, 7883-7890.
29. Cleij, M., Archelas, A., Furstoss, R., 1998. Microbiological transformations. Part 42: A two-liquid-phase preparative scale process for an epoxide hydrolase catalysed resolution of para-bromo-α-methyl styrene oxide. Occurrence of a surprising enantioselectivity enhancement.. Tetrahedron Asymmetry 9, 1839-1842.
30. Cooke, R., Kuntz, I.D., 1974. The properties of water in biological systems. Ann. Rev. Biophys. Bioeng. 3, 95-126.
31. Colombo, G., Ottolina, G., Carrea, G., Bernardi, A., Scolastico, C., 1998. Application of structure-based thermodynamic calculations to the rationalization of the enantioselectivity of substilisin in organic solvents. Tetrahedron Asymmetry 9, 1205-1214.
32. Conde, S., Fierros, M., Rodríguez-Franco, M.I., Puig, C., 1998. Resolution of 1-(4-amino-3-chloro-5-cyanophenyl)-2-bromo-1-ethanol by lipase mediated enantioselective alcoholysis, hydrolysis and acylation. Tetrahedron Asymmetry 9, 2229-2232.
33. Davies, H.G., Green, R.H., Kelly, D.R., Roberts, S.M., 1989. Biotransformations in Preparative Organic Chemistry. Academic Press, London.
34. Dong, H., Wang, H.D., Cao, S.G., Shen, J.C., 1998. Lipase-catalysed polymerisation of lactones and linear hydroxyesters. Biotechnol. Lett. 20, 905-908.
35. Easton, C.J., Harper, J.B., 1998. Acylase I catalyse hydrolysis of para-substituted (S)-phenylalanine derivatives from mixtures of the racemic ortho- and para-substituted isomersTrans S. Tetrahedron Lett. 39, 5269-5272.
36. Ema, T., Sugiyama, Y., Fukumoto, M., Moriya, H., Cui, J.N., Sakai, T., Utaka, M., 1998. Highly enantioselective reduction of carbonyl compounds using a reductase purified from bakers' yeast. J. Org. Chem. 63, 4996-5000.
37. Faber, K., 1995. Biotransformations in Organic Chemistry, second edition. Springer, New York.
38. Fang, J.W., Li, J., Chen, X., Zhang, Y.N., Guo, Z.M., Zhang, W., Yu, L.B., Brew, K., Wang, P.G., 1998. Highly efficient chemoenzymatic synthesis of α-galactosyl epitopes with a recombinant α(1-3)-galactosyltransferase. J. Am. Chem. Soc. 120, 6635-6638.
39. Findeis, M.H., Whitesides, G.M., 1987. Fumarase-catalysed synthesis of L-threo-chloromalic acid and its conversion to 2-deoxy-D-ribose and D-erthyro-sphingosine. J. Org. Chem. 52, 2838-2848.
40. Fishman, A., Zviely, M., 1998a. Chemo-enzymatic synthesis of (S)-α-cyano-3-phenoxybenzyl alcohol. Tetrahedron Asymmetry 9, 107-118.
41. Fishman, A., Basheer, S., Shatzmiller, S., Cogan, U., 1998b. Fatty-acid-modified enzymes as enantioselective catalysts in microaqueous organic media. Biotech. Lett. 20, 535-538.
42. Fitzpatrick, P.A., Klibanov, A.M., 1991. How can the solvent affect enzyme enantioselectivity. J. Am. Chem. Soc. 113, 3166-3171.
43. Forró, E., Kanerva, L.T., Fulop, F., 1998. Lipase-catalysed resolution of 2-dialkylaminomethylcyclohexanols. Tetrahedron Asymmetry 9, 513-520.
44. Fritz-Langhals, E., Kunath, B., 1998. Synthesis of aromatic aldehydes by laccase-mediator assisted oxidation. Tetrahedron Lett. 39, 5955-5956.
45. Fuganti, C., Grasselli, P., 1977. Transformations of non-conventional substrates by fermenting baker's yeast: Production of optically active methyl-diols from aldehydes. Chem. Ind. 983.
46. Fukunaga, K., Maruoka, N., Sugimura, Y., Nakao, K., Shimizu, T., 1998. Preparation of the gemini detergent lipase complexes and their high enzymatic activities in the transesterification in homogenous organic solvents. Biotech. Lett. 20, 1161-1165.
47. Fukusima, Y., Hayashi, M., Fujiwara, M., Miyagawa, T., Yoshikawa, G., Yano, T., Nakajima, H., 1998. Enzymatic synthesis of carbocyclic analogues of fructose-2,6-bisphosphate with 6-phosphofructo-2-kinase. Chem. Lett. 7, 575-576.
48. GarciaGranados, A., Parra, A., Simeö, Y., Extremera, A.L., 1998. Chemical, enzymatic and microbiological synthesis of 8,12-eudesmanolides: Synthesis of sivasinolide and yomogin analogues. Tetrahedron 54, 14421-14436.
49. Gargouri, M., Legoy, M.D., 1998. Biosynthesis and analysis of 3Z-nonenal. Biotech. Lett. 20, 23-26.
50. Gibbs, G., Hateley, M.J., McLaren, L., Welham, M., Willis, C.L., 1999. Enantioselective synthesis of 3-hydroxypiperidin-2-ones. Tetrahedron Lett. 40, 1069-1072.
51. Griengl, H., Klempier, N., Pöchlauer, P., Schmidt, M., Shi, N.Y., Zabelinskaja-Mackova, A.A., 1998. Enzyme catalysed formation of (S)-cyanohydrins derived from aldehydes and ketones in a biphasic solvent system. Tetrahedron 54, 14477-14486.
52. Gutman, A.L., Zuobi, K., Guibé-Jampel, E., 1990. Lipase catalysed hydrolysis of γ-substituted α-aminobutyrolactones. Tetrahedron Lett., 2037-2038.
53. Haneda, K., Inazu, T., Mizuno, M., Iguchi, R., Yamamoto, K., Kumagai, H., Aimoto, S., Suzuki, H., Noda, T., 1998. Chemoenzymatic synthesis of calcitonin derivatives containing N-linked oligosaccharides. Bioorg. Med. Chem. Lett. 8, 1303-1306.
54. Häring, D., Schüler, E., Adam, W., Saha-Möller, C.R., Schreier, P., 1999. Semisynthetic enzymes in asymmetric synthesis: Enantioselective reduction of racemic hydroperoxides catalysed by seleno-subtilisin. J. Org. Chem. 64, 832-835.
55. Häring, D., Schreier, P., 1998. Novel biocatalysts by chemical modification of known enzymes: Cross-linked microcrystals of the semisynthetic peroxidase seleno-subtilisin. Angew. Chem. Int. Ed. 37, 2471-2473.
56. Hirata, T., Izumi, S., Ogura, M., Yawata, T., 1998. Epoxidation of styrenes with the peroxidase from the cultured cells of Nicotiana tobacum. Tetrahedron 54, 15993-16003.
57. 13C-labelled isopentenyl diphosphate. Tetrahedron Lett. 39, 2033-2036.
58. Kawai, Y., Hayaashi, M., Inaba, Y., Saitou, K., Ohno, A., 1998a. Asymmetric reduction of α,β-unsaturated ketones with a carbon-carbon double-bond reductase from bakers' yeast. Tetrahedron Lett. 39, 5225-5228.
59. Kawai, Y., Hida, K., Dao, D.H., Ohno, A., 1998b. Asymmetric synthesis of β-hydroxy esters having three consecutive chiral centers with a reductase from bakers' yeast. Tetrahedron Lett. 39, 9219-9222.
60. Ke, T., Wescott, C.R., Klibanov, A.M., 1996. Prediction of the solvent dependence of enzymatic prochiral selectivity by means of structure-based thermodynamic calculations. J. Am. Chem. Soc. 118, 3366-3374.
61. Kielbasínski, P., Góralczyk, P., Mikolajczyk, M., Wieczorek, M.W., Majzner, W.R., 1998. Enzyme-promoted kinetic resolution of racemic P-chiral phosphonyl and phosphorylacetates. Tetrahedron Asymmetry 9, 2641-2650.
62. Kim, B.W., Choi, J.W., Yun, J.W., 1998. Selective production of GF(4)-fructooligosaccharide from sucrose by a new transfructosylating enzyme. Biotech. Lett. 20, 1031-1034.
63. Kise, K.J., Bowler, B.E., 1998. Enantioselective synthesis of an unnatural amino acid and its incorporation into a peptide. Tetrahedron Asymmetry 9, 3319-3324.
64. Klibanov, A.M., 1990. Asymmetric transformations catalysed by enzymes in organic solvents. Acc. Chem. Res. 23, 114-120.
65. Kline, B.J., Beckman, E.J., Russell, A.J., 1998. One-step biocatalytic synthesis of linear polyesters with pendant hydroxy groups. J. Am. Chem. Soc. 120, 9475-9480.
66. Koh, S., Shin, H.J., Kim, J.S., Lee, D.S., Lee, S.Y., 1998. Trehalose synthesis from maltose by a thermostable trehalose synthase from Thermos caldophilus. Biotech. Lett. 20, 757-761.
67. Kroutil, W., Orru, R.V.A., Faber, K., 1998. Stabilization of Nocardia EH1 epoxide hydrolase by immobilization. Biotech. Lett. 20, 373-377.
68. Kurahashi, T., Mizutani, T., Yoshida, J., 1999. Effect of intramolecular hydrogen-bonding network on the relative reactivities of carbohydrate OH groups. J. Chem. Soc. Perkin Trans, 1, 465-473.
69. Layh, N., Willetts, A., 1998. Enzymatic nitrile hydrolysis in low water systems. Biotech. Lett. 20, 329-331.
70. Leak, D.J., Aikens, P.J., Seyed-Mahmoudian, M., 1992. The microbial production of epoxides. Trends Biotechnol. 10, 256-261.
71. Leblanc, D., Morin, A., Gu, D., Zhang, X.M., Bisaillon, J.G., Paquet, M., Dubeau, H., 1998. Short chain fatty ester synthesis by commercial lipases in low-water systems and by resting microbial cells in aqueous medium. Biotech. Lett. 20, 1127-1131.
72. Lemeire, G.L., Lepoivre, J.A., Alderweireldt, F.C., 1985. Hlad-catalysed oxidation of alcohols with acetaldehyde as a coenzyme recycling substrate. Tetrahedron Lett. 26, 4527-4528.
73. Lin, G., Lin, W.Y., Shieh, C.T., 1998. The enhancement of enantioselectivities for lipase-catalysed reactions by using carbamates. Tetrahedron Lett. 40, 8881-8884.
74. Liu, W., Kumar, J., Tripathy, S., Senecal, K.J., Samuelson, L., 1999a. Enzymatically synthesised conducting polyaniline. J. Am. Chem. Soc. 121, 71-78.
75. Liu, J.Q., Luo, G.M., Zhang, K., Chen, X.F., Shen, J.C., 1999b. Generation of a glutathione peroxidase-like mimic using bioim-printing and chemical mutation. J. Chem. Soc., Chem. Commun. 20, 199-200.
76. Loane, C., Boeren, S., Vos, K., Veeger, C., 1987. Biotechnol. Bioeng. 30, 81.
77. 1, leaving group, site of subtilisin Bacillus lentus using an enzyme-catalysed transesterification reaction. Tetrahedron Asymmetry 9, 551-561.
78. Ma, Y.A., Guo, Z.W., Sih, C.J., 1998. Enzymatic oxidative coupling of monohalogenated tyrosine derivative. Tetrahedron Lett. 39, 9357-9360.
79. Mahmoudian, M., Rudd, B.A.M., Cox, B., Drake, C.S., Hall, R.M., Stead, P., Dawson, M.J., Chandler, M., Livermore, D.O., Turner, N.J, Jenkins, G., 1998. A versatile procedure for the generation of nucleoside 5'-carboxylic acids using nucleoside oxidase. Tetrahedron 54, 8171-8182.
80. Matoishi, K., Sano, A., Imai, N., Yamazaki, T., Yokoyama, M., Sugai, T., Ohta, H., 1998. Rhodococcus rhodochrous IFO 15564-mediated hydrolysis of alicyclic nitriles and amides: Stereoselectivity and use for kinetic resolution and asymmetrization. Tetrahedron Asymmetry 9, 1097-1102.
81. May, S.W., 1979. Enzyme epoxidation reactions. Enzyme. Micro. Technol. 1, 15-22.
82. Menger, F.M., 1993. Enzyme reactivity from an organic perspective. Acc. Chem. Res. 26, 206-212.
83. Mori, T., Okahata, Y., 1998. Effective biocatalytic transgalactosylation in a supercritical fluid using a lipid-coated enzyme. J. Chem. Soc., Chem. Commun. 20, 2215-2216.
84. Moussou, P., Archelas, A., Baratti, J., Furtoss, R., 1998. Microbiological Transformation. Part 39: Determination of the regioselectivity occurring during oxirane ring opening by epoxide hydrolases: A theoretical analysis and a new method for its determination. Tetrahderon Asymmetry 9, 1539-1547.
85. 2O mediated macrolactonisation: Formal chemoenzymatic synthesis of macrolide antibiotic (-)-A26671B. Tetrahedron Lett. 40, 1207-1210.
86. Nägele, E., Schelhaas, M., Kuder, N., Waldmann, H., 1998. Chemoenzymatic synthesis of N-Ras-lipopeptides. J. Am. Chem. Soc. 102, 6889-6902.
87. Nakamura, K., Matsuda, T., 1998. Asymmetric reduction of ketones by the acetone powder of Geotrichum candidum. J. Org. Chem. 63, 8957-8964.
88. Nawani, N., Dosanjh, N.S., Kaur, J., 1998. A novel thermostable lipase from a thermophilic Bacillus sp.: Characterization and esterification studies. Biotech. Lett. 20, 997-1000.
89. Neidleman, S.L., Geigert, J., 1983. The enzymatic synthesis of heterogenous dihalide derivatives: A unique biocatalytic discovery. Trends. Biotechnol. 1, 21-25.
90. Oikawa, H., Kobayashi, T., Katayama, K., Suzuki, Y., Ichihara, A., 1998. Total synthesis of (-)-solanapyrone A via enzymatic Diels-Alder reaction of prosolanapyrone.Trans -. J.Org. Chem. 63, 8748-8756.
91. Otto, R.T., Bornscheuer, U.T., Syldatk, C., Schmid, R.D., 1998. Synthesis of aromatic n-alkyl-gluoside esters in a coupled β-glucosidase and lipase reaction. Biotech. Lett. 20, 437-440.
92. 2. Biotech. Lett. 21, 65-69.
93. Parmar, V.S., Pati, H.N., Azim, A., Kumar, R., Himanshu, , Bisht, K.S., Prasad, A.K., Errington, W., 1998. Lipase-catalysed selective deacetylation of phenolic/enolic acetoxy groups in peracetylated benzyl phenyl ketones. Bioorg. Med. Chem. 6, 109-118.
94. Partridge, J., Halling, P.J., Moore, B.D., 1998. Practical route to high activity enzyme preparations for synthesis in organic media. J. Chem. Soc., Chem. Commun. 7, 841-842.
95. Pchelka, B., Radomska, J., Plenkiewicz, J., 1998. Lipase-catalysed kinetic resolution of the racemic mixtures of 1-aryloxy-3-nitrato-and 1-aryloxy-3-azido-2-propanols. Syn. Comm. 28, 4355-4364.
96. Phillips, R.S., May, S.W., 1981. Enzymic sulfur oxidation reactions. Enzyme. Micro. Technol. 3, 9-18.
97. Pitt, M.J., Easton, C.J., Robertson, T.A., Kumaratilake, L.M., Ferrante, A., Poulos, A., Rathjen, D.A., 1998. Synthesis of hydroperoxide and perketal derivatives of polyunsaturated fatty acids as potential anti-malarial agents. Tetrahedron Lett. 39, 4401-4404.
98. Rama, R., Mougin, C., Boyer, F.D., Kollmann, A., Malosse, C., Sigoillot, J.C., 1998. Biotransformations of benzoapyrene in a bench scale reactor using laccase of Pycnoporus connabarinus. Biotech. Lett. 20, 1101-1104.
99. del-Rio, J.L., Faus, I., 1998. Resolution of (+/-)-trans-2-phenylcyclohexano-1ol by lipases from Candida rugosa, effect of catalyst source and reaction conditions. Biotechnol. Lett. 20, 1021-1025.
100. Roberts, S.M., 1998. Preparative biotransformations: the employment of enzymes and whole cells in synthetic organic chemistry. J. Chem. Soc., Perkin Trans. 1, 157-169.
101. Roberts, S.M., 1999. Preparative biotransformations. J. Chem. Soc., Perkin Trans., 1-21.
102. Sakai, T., Miki, Y., Nakatani, M., Ema, T., Uneyama, K., Utaka, M., 1998a. Lipase-catalysed kinetic resolution of 2-acyloxy-2-(pentafluorophenyl) acetonitrile. Tetrahedron Lett. 39, 5233-5236.
103. Sakai, T., Kishimoto, T., Tanaka, Y., Ema, T., Utaka, M., 1998b. Low-temperature method for enhancement of enantioselectivity in the lipase-catalysed kinetic resolutions of solketal and some chiral alcohols. Tetrahedron Lett. 39, 7881-7884.
104. Sakurai, T., Margolin, A.L., Russell, A.J., Klibanov, A.M., 1988. Control of enzyme enantioselectivity by the reaction medium. J. Am. Chem. Soc. 110, 7236-7237.
105. Sanchez Sancho, F.S., Herradon, B., 1998. Short syntheses of (S)-pipecolic acid, (R)-coniine and (S)-delta-coniceine using biocatalytically-generate chiral building blocks. Tetrahedron Asymmetry 9, 1951-1965.
106. Sano, S., Hayashi, K., Miwa, T., Ishii, T., Fujii, M., Mima, H., Nagao, Y., 1998. New enantiodivergent procedure for the syntheses of chiral α-substituted serines from α-alkyl-α-aminomalonates utilizing enzymatic hydrolysis. Tetrahedron Lett. 39, 5571-5574.
107. Santaniello, E., Ferraboschi, F., Grisenti, P., Manzocchi, A., 1992. The biocatalytic approach to the preparation of enantiomerically pure chiral building blocks. Chem. Rev. 92, 1071-1140.
108. Schoevaart, R., van Rantwijk, F., Sheldon, R.A., 1999. Class I fructose-1,6-bisphosphate aldolases as catalysts for asymmetric aldol reactions. Tetrahedron Asymmetry 10, 705-711.
109. Shefylan, G.Y., Howe, D.L., Wilson, T.L., Woodward, R.W., 1998. Enzymatic synthesis of 3-deoxy-D-manno-octulosonate 8-phosphate, 3-deoxy-D-altro-octulosonate 8-phosphate, 3,5-dideoxy-D-gluco (manno)-octulosonate 8-phosphate by 3-deoxy-D-arabino-heptulosonate 7-phospate synthase. J. Am. Chem. Soc. 120, 11027-11032.
110. Sih, C. J., Wu, S-H., 1989. in: Eliel, E.L., Allinger, N. L., Denmark, S.E., (Eds.), Topics in Stereochemistry, vol. 19. Interscience, New York, pp. 63.
111. Smith, B.J., Lawrence, M.C., Barbosa, J.A.R.G., 1999. Substrate-assisted catalysis in sialic acid aldolase. J. Org. Chem. 64, 945-949.
112. Sridhar, M.M., Vadivel, S.K., Bhalerao, U.T., 1998. Novel method for preparation of symmetric disulfide from thiols using enzyme catalysis. Synthetic Commun. 28, 1499-1502.
113. Stewart, J.D., Reed, K.W., Martinez, C.A., Zhu, J., Chen, G., Kayser, M.M., 1998. Recombinant baker's yeast as a whole-cell catalyst for asymmetric Baeyer-Villiger oxidations. J. Am. Chem. Soc. 120, 3541-3548.
114. Sutherland, A., Willis, C.L., 1998. Chemoenzymatic synthesis of 4-amino-2-hydroxy acids. A comparison of mutant and wild type oxidoreductases. J. Org. Chem. 63, 7764-7769.
115. Suwasono, S., Rastall, R.A., 1998. Synthesis of oligosaccharides using immobilised 1,2-α-mannosides from Apergillus phoenicis, Immobilisation-dependent modulation of product spectrum. Biotechnol. Lett. 20, 15-17.
116. Sweers, H.M., Wong, C.-H., 1986. Enzyme-catalysed regioselective deacylation of protected sugars in carbohydrate synthesis. J. Am. Chem. Soc. 108, 6421-6422.
117. 2t-isoprostane. Tetrahedron 54, 11767-11782.
118. Taylor, S.J.C., Sutherland, A.G., Lee, C., Wisdom, R., Thomas, S., Roberts, S.M., Evans, C., 1990. Chemoenzymatic synthesis of (-)-carbovir utilising a whole cell catalysed resolution of 2-azabicyclo[2.2.1]hept-5-en-3-one. J. Chem. Soc. Chem. Commun. 1120-1121.
119. Toone, E.J., Simon, E.S., Benarski, M.D., Whitesides, G.M., 1989. Enzyme-catalysed synthesis of carbohydrates. Tetrahedron 45, 5365-5422.
120. Turner, N.J., 1994. Recent advances in the use of enzyme-catalysed reactions in organic synthesis. Nat. Prod. Rep. 11, 1-15.
121. van Unen, D.J., Sakodinskaya, I.K., Engbersen, J.F.J., Reinhoudt, D.N., 1998. Crown ether activation of cross-linked substilisin Carslberg crystals in organic solvents. J. Chem. Soc., Perkin Trans I. 3341-3343.
122. Ursini, A., Maragni, P., Bismara, C., Tamburini, B., 1999. Enzymatic method of preparation of optically active trans-2-amino cyclohexanol derivatives. Synthetic. Commun. 29, 1369-1377.
123. vande Veldt, F., Konemann, L., van Rantwijk, F., Sheldon, R.A., 1998. Enantioselective sulfoxidation mediated by vandium-incorporated phytase: A hydrolase acting as a peroxidase. J. Chem. Soc., Chem. Commun. 17, 1891-1892.
124. Weber, N., Klein, E., Mukherjee, K.D., 1999. Long-chain thioesters prepared by solvent-free thioesterification and transthioesterification catalysed by microbial lipases. Appl. Micro. Biotechnol. 51, 401-404.
125. Werschkun, B., Wendt, A., Thiem, J., 1998. Enzymatic synthesis of β-glucuronides of estradiol, ethynylestradiol and other phenolic substrates on a preparative scale employing UDP-glucuronyl transferase. J. Chem. Soc., Perkin Trans. 3021-3023.
126. Wescott, C.R., Klibanov, A.M., 1994. The solvent dependence of enzyme specificity. Biochim. Biophys. Acta. 1206, 1-9.
127. Wieser, M., Yoshida, T., Hagasawa, T., 1998. Microbial synthesis of pyrrole-2-carboxylate by Baccilus megaterium PYR2910. Tetrahedron Lett. 39, 4309-4310.
128. Xing, G.W., Liu, D.J., Ye, Y.H., Ma, J.M., 1999. Enzymatic synthesis of oligopeptides in mixed reverse micelles. Tetrahedron Lett. 40, 1971-1974.
129. Yuan, D.Q., Dong, S.D., Breslow, R., 1998. Cyclodextrin-base class I aldolase enzyme mimics to catalyse crossed aldol condensations. Tetrahedron Lett. 39, 7673-7676.
130. Zhao, Z.Y., Mabic, S., Kuttab, S., Francot, C., Castagnoli, K., Catagnoli, N., 1998. Rat liver microsomal enzyme catalysed oxidation of 1-cyclopropyl-4-phenyl-1,2,3,6-tetrahydropyridine. Bioorg. Med. Chem. 6, 2531-2539.