Biocatalytic synthesis of optically active α-oxyfunctionalized carbonyl compounds

Accounts of Chemical Research

Volumn 32, Issue 10, 1999, Pages 837-845

  Adam, Waldemar ^a   Lazarus, Michael ^a   Saha Möller, Chantu R ^a   Schreier, Peter ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; CARBONYL DERIVATIVE; DIPEPTIDYL CARBOXYPEPTIDASE INHIBITOR; LEUKOTRIENE RECEPTOR BLOCKING AGENT;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; OPTICAL ROTATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0032736221     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar980062i     Document Type: Article

References (61)

1. Stinson, S. C. Chiral Drug Market Shows Signs of Maturity. Chem. Eng. News 1997, 20, 38-70.
2. For enzymes in organic synthesis see: (a) Wong, C. H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry, Pergamon: New York, 1994.
3. (b) Drauz, K.; Waldmann, H. Enzyme Catalysis in Organic Synthesis; VCH: Weinheim, 1995.
4. Faber, K. Biotransformations in Organic Chemistry; Springer: Berlin, 1997.
5. Kvittingen, L. Some Aspects of Biocatalysis in Organic Solvents. Tetrahedron 1994, 50, 8253-8274.
6. Mori, K.; Takigawa, T.; Matsuo, T. Synthesis of Optically Active Forms of Ipsdienol and Ipsenol-The Pheromone Components of Ips Bark Beetles. Tetrahedron 1979, 35, 933-940.
7. Mulzer, J. In Organic Synthesis Highlights; Mulzer, J., Altenbach, H.-J., Braun, M., Krohn, K., Reissig, H.-U. Eds.; VCH: Weinheim, 1991; pp 243-250.
8. Davis, F. A.; Chen, B.-C. Asymmetric Hydroxylation of Enolates with N-Sulfonyloxaziridines. Chem. Rev. 1992, 92, 919-934.
9. (a) Attwood, M. R.; Francis, R. J.; Hassall, C. H.; Kröhn, A.; Lawton, G.; Natoff, I. L.; Nixon, J. S.; Redshaw, S.; Thomas, W. A. New Potent Inhibitors of Angiotensin Converting Enzyme. FEBS Lett. 1984, 165, 201-206.
10. (b) Cohen, N.; Weber, G.; Banner, B. L.; Lopresti, R. J.; Schaer, B.; Focella, A.; Zenchoff, G. B.; Chiu, A. M.; Todaro, L.; O'Donnell, M.; Welton, A. F.; Brown, D.; Garrippa, R.; Crowley, H.; Morgan, D. W. 3,4-Dihydro-2H-benzopyran-2-carboxylic Acids and Related Compounds as Leukotriene Antagonists. J. Med. Chem. 1989, 32, 1842-1860.
11. Kawai, G.; Ikeda, Y. Chemistry and Functional Moiety of a Fruiting-Inducing Cerebroside in Schizophyllum Commune. Biochim. Biophys. Acta 1983, 754, 243-248.
12. Evans, D. A.; Morrissey, M. M.; Dorow, R. L. Asymmetric Oxygenation of Chiral Imide Enolates. A General Approach to the Synthesis of Enantiomerically Pure α-hydroxy Carboxylic Acid Synthons. J. Am. Chem. Soc. 1985, 107, 4346-4348.
13. Massad, S. K.; Hawkins, L. D.; Baker, D. C. A Series of (2S)-2-O-Protected-2-hydroxypropanals(L-Lactal-dehydes) Suitable for Use as Optically Active Inter-mediates. J. Org. Chem. 1983, 48, 5180-5182.
14. (a) Davis, F. A.; Sheppard, A. C.; Chen, B.-C.; Haque, M. S. Chemistry of Oxaziridines. 14. Asymmetric Oxidation of Ketone Enolates Using Enantiomerically Pure (Camphorylsulfonyl)oxaziridine. J. Am. Chem. Soc. 1990, 112, 6679-6690.
15. (b) Adam, W.; Prechtl, F. Enantioselective Oxidation of Chiral Titanium Enolates Derived from Propiophenone by Dimethyldioxirane or 3-Phenyl-2-phenyl-sulfonyl-oxaziridine. Chem. Ber. 1994, 127, 667-671.
16. Adam, W.; Fell, R. T.; Stegmann, V. R.; Sana-Möller, C. R. Synthesis of Optically Active α-Hydroxy Carbonyl Compounds by the Catalytic, Enantioselective Oxidation of Silyl Enol Ethers and Ketene Acetals with (Salen)manganese(III) Complexes. J. Am. Chem. Soc. 1998, 120, 708-714.
17. Adam, W.; Fell, R. T.; Saha-Möller, C. R.; Zhao, C.-G. Synthesis of Optically Active α-Hydroxy Ketones by Enantioselective Oxidation of Silyl Enol Ethers with a Fructose-Derived Dioxirane. Tetrahedron: Asymmetry 1998, 9, 397-401.
18. (e) Adam, W.; Saha-Möller, C. R.; Zhao, C.-G. Enantioselective Oxidation of vic-Diols to Optically Active α-Hydroxy Ketones by a Fructose-Derived Dioxirane. Tetrahedron: Asymmetry 1998, 9, 4117-4122.
19. Adam, W.; Fell, R. T.; Hoch, U.; Saha-Möller, C. R.; Schreier, P. Kinetic Resolution of Chiral α-Hydroperoxy Esters by Horseradish Peroxidase-Catalyzed Enantioselective Reduction to α-Hydroxy Esters. Tetrahedron: Asymmetry 1995, 6, 1047-1050.
20. Adam, W.; Lazarus, M.; Boss, B.; Saha-Möller, C. R.; Schreier, P. Enzymatic Resolution of Chiral 2-Hydroxy Carboxylic Acids by Enantioselective Oxidation with Molecular Oxygen Catalyzed by the Glycolate Oxidase from Spinach (Spinacia oleracea). J. Org. Chem. 1997, 62, 7841-7843.
21. Adam, W.; Lazarus, M.; Saha-Möller, C. R.; Schreier, P. Quantitative Transformation of Racemic 2-Hydroxy Acids into (R)-2-Hydroxy Acids by Enantioselective Oxidation with Glycolate Oxidase and Sub-sequent Reduction of 2-Keto Acids with D-Lactate Dehydrogenase. Tetrahedron: Asymmetry 1998, 9, 351-355.
22. (a) Adam, W.; Lazarus, M.; Saha-Möller, C. R.; Humpf, H.-U.; Schreier, P. Enantioselecctive α Hydroxylation of Carboxylic Acids with Molecular Oxygen Catalyzed by the a Oxidation Enzyme System of Young Pea Leaves (Pisum sativum): A Substrate Selectivity Study. Tetrahedron: Asymmetry 1996, 7, 2287-2292.
23. (b) Adam, W.; Boland, W.; Hartmann-Schreier, J.; Lazarus, M.; Saffert, A.; Saha-Möller, C. R.; Schreier, P. α Hydroxylation of Carboxylic Acids with Molecular Oxygen Catalyzed by the a Oxidase of Peas (Pisum sativum): A Novel Biocatalytic Synthesis of Enantiomerically Pure (R)-2-Hydroxy Acids. J. Am. Chem. Soc. 1998, 120, 11044-11048.
24. Adam, W.; Diaz, M. T.; Fell, R. T.; Saha-Möller, C. R. Kinetic Resolution of Racemic α-Hydroxy Ketones by Lipase-Catalyzed Irreversible Transesterification. Tetrahedron: Asymmetry 1996, 7, 2207-2210.
25. Adam, W.; Lazarus, M.; Schmerder, A.; Humpf, H.-U.; Saha-Möller, C. R.; Schreier, P. Synthesis of Optically Active α-Hydroxy Acids by Kinetic Resolution Through Lipase-Catalyzed Enantioselective Acetylation. Eur. J. Org. Chem. 1998, 2013-2018.
26. Adam, W.; Diaz, M. T.; Saha-Möller, C. R. Lipase-Catalyzed Kinetic Resolution of ,β-Unsaturated α'-Acetoxy Ketones. Tetrahedron: Asymmetry 1998, 9, 791-796.
27. Csuk, R.; Glänzer, B. I. Baker's Yeast Mediated Transformations in Organic Chemistry. Chem. Rev. 1991, 91, 49-97.
28. Nakamura, K.; Kondo, S.; Nakajima, N.; Ohno, A. Mechanistic Study for Stereochemical Control of Microbial Reduction of α-Keto Esters in an Organic Solvent. Tetrahedron 1995, 51, 687-694.
29. Nakamura, K.; Kondo, S.; Kawai, Y.; Hida, K.; Kitano, K.; Ohno, A. Enantio-and Regioselective Reduction of α-Diketones by Baker's Yeast. Tetrahedron: Asymmetry 1996, 7, 409-412.
30. Ridley, D. D.; Stralow, M. Stereospecific Asymmetric Reduction of Functionalized Ketones. J. Chem. Soc., Chem. Commun. 1975, 400.
31. Adam, W.; Lazarus, M.; Saha-Möller, C.R.; Weichold, O.; Hoch, U.; Häring, D.; Schreier, P. Biotransformations with Peroxidases. In Advances in Biochemical Engineering Biotechnology: Biotransformations; Faber, K., Ed.; Springer: Berlin, 1998; Vol. 63, pp 73-108.
32. (a) Adam, W.; Hoch, U.; Saha-Möller, C. R.; Schreier, P. Enzyme-Catalyzed Asymmetric Synthesis: Kinetic Resolution of Chiral Hydroperoxides by Enantioselective Reduction to Alcohols with Horseradish Peroxidase. Angew. Chem., Int. Ed. Engl. 1993, 32, 2, 1737-1739.
33. (b) Adam, W.; Hoch, U.; Lazarus, M.; Saha-Möller, C. R.; Schreier, P. Enzyme-Catalyzed Asymmetric Synthesis: Kinetic Resolution of Race-mic Hydroperoxides by Enantioselective Reduction to Alcohols with Horseradish Peroxidase. J. Am. Chem. Soc. 1995, 117, 11898-11901.
34. Adam, W.; Mock-Knoblauch, C.; Saha-Möller, C. R. Biocatalytic Kinetic Resolution of Hydroperoxy Vinylsilanes by Horseradish Peroxidase (HRP) and Lipases, a Comparative Study. Tetrahedron: Asymmetry 1997, 8, 1947-1950.
35. Adam, W.; Lazarus, M.; Hoch, U.; Korb, M. N.; Saha-Möller, C. R.; Schreier, P. Horseradish Peroxidase (HRP)-Catalyzed Enantioselective Reduction of Racemic Hydroperoxy Homoallylic Alcohols: A Novel Enzymatic Method for the Preparation of Optically Active, Unsaturated Diols and Hydroperoxy Alcohols. J. Org. Chem. 1998, 63, 6123-6127.
36. Chen, C.-S.; Fujimoto, Y.; Girdaukas, G., Sih, C. Quantitative Analyses of Biochemical Kinetic Resolutions of Enantiomers. J. Am. Chem. Soc. 1982, 104, 7294-7299.
37. Hoch, U.; Adam, W.; Fell, R.; Saha-Möller, C. R.; Schreier, P. Horseradish Peroxidase-A Biocatalyst for the One-Pot Synthesis of Enantiomerically Pure Hydroperoxides and Alcohols. J. Mol. Catal. A: Chem. 1997, 117, 321-328.
38. Kim, M.-J.; Whitesides, G. M. L-Lactate Dehydrogenase: Substrate Specificity and Use as a Catalyst in the Synthesis of Homochiral 2-Hydroxy Acids. J. Am. Chem. Soc. 1988, 110, 2959-2964.
39. Bur, D.; Luyten, M. A.; Wynn, H.; Provencher, L. R.; Jones, J. B.; Gold, M.; Friesen, J. D.; Clarke, A. R.; Holbrook, J. J. An Evaluation of the Substrate Specificity and Asymmetric Synthesis Potential of the Cloned L-Lactate Dehydrogenase from Bacillus stearothermophilus. Can. J. Chem. 1989, 67, 1065-1070.
40. Wu, C.-Y.; Chen, S.-T.; Chiou, S.-H.; Wang, K.-T. Kinetic Analysis of Duck ∈-Crystallin with L-Lactate Dehydrogenase Activity: Determination of Kinetic Constants and Comparison of Substrate Specificity. Biochem. Biophys. Res. Commun. 1992, 186, 874-880.
41. Simon, E. S.; Plante, R.; Whitesides, G. M. L-Lactate Dehydrogenase. Substrate Specificity and Use as a Catalyst in the Synthesis of Homochiral 2-Hydroxy Acids. Appl. Biochem. Biotechnol. 1989, 22, 169-179.
42. Kallwass, H. K. W. Potential of R-2-Hydroxyisocaproate Dehydrogenase from Lactobacillus casei for Stereospecific Reductions. Enzyme Microb. Technol. 1992, 14, 28-35.
43. Schütte, H.; Hummel, W.; Kula, M.-R. L-2-Hydroxyisocaproate Dehydrogenase - A New Enzyme from Lactobacillus confusus for the Stereospecific Reduction of 2-Ketocarboxylic Acids. Appl. Microbiol. Biotechnol. 1984, 19, 167-176.
44. Jones, J. B. An Illustrative Example of a Synthetically Useful Enzyme: Horse Liver Alcohol Dehydrogenase. In Enzymes in Organic Synthesis, Ciba Foundation Symposium 111; Pitman: London, 1985; pp 3-21.
45. Wong, C.-H.; Matos, J. R. Enantioselective Oxidation of 1,2-Diols to L-α-Hydroxy Acids Using Coimmobilized Alcohol and Aldehyde Dehydrogenases as Catalysts. Org. Chem. 1985, 50, 1992-1994.
46. Lee, L. G.; Whitesides, G. M. Preparation of Optically Active 1,2-Diols and α-Hydroxy Ketones Using Glycerol Dehydrogenase as Catalyst: Limits to Enzyme-Catalyzed Synthesis due to Noncompetitive and Mixed Inhibition by Product. J. Org. Chem. 1986, 51, 25-36.
47. (a) Nishimura, M.; Akhmedov, Y. D.; Strzalka, K.; Akazawa, T. Purification and Characterization of Glycolate Oxidase from Pumpkin Cotyledons. Arch. Biochem. Biophys. 1983, 222, 397-402.
48. (b) Schuman, M.; Massey, V. Purification and Characterization of Glycolate Oxidase from Pig Liver. Biochim. Biophys. Acta 1971, 227, 500-520.
49. Macheroux, P.; Massey, V.; Thiele, D. J.; Volokita, M. Expression of Spinach Glycolate Oxidase in Saccharomyces cerevisiae: Purification and Characterization. Biochemistry 1991, 30, 4612-4619.
50. Shine, W. E.; Stumpf, P. K. Fat Metabolism in Higher Plants. Recent Studies on Plant α-Oxidation Systems. Arch. Biochem. Biophys. 1974, 162, 147-157.
51. Kajiwara, T.; Yoshikawa, H.; Saruwatari, T.; Hatanaka, A.; Kawai, T.; Ishihara, M.; Tsuneya, T. Enzymatic Formation of Unsaturated Long Chain Fatty Aldehydes in Ulva Pertusa. Phytochem. 1988, 27, 1643-1645.
52. Kajiwara, T.; Matsui, K.; Akakabe, Y. Biogeneration of Flavor Compounds via Oxylipins in Edible Seaweeds. In Biotechnology for Improved Foods and Flavours; Takeoaka, G. R., Teranishi, R., Williams, P. J., Kobayashi, A., Eds.; American Chemical Society: Washington, 1996; pp 146-166.
53. Kagan, H. B. Asymmetric Oxidation of Sulfides. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers: New York, 1993; pp 203-226.
54. Koljak, R.; Boutaud, O.; Shieh, B.-H.; Samel, N.; Brash, A. R. Identification of a Naturally Occurring Peroxidase-Lipoxygenase Fusion Protein. Science 1997, 277, 1994-1996.
55. Sugai, T.; Ohta, H. Lipase-Catalyzed Kinetic Resolution of 2-Hydroxyhexa-decanoic Acid and its Esters. Agric. Biol. Chem. 1990, 54, 3337-3338.
56. Miyazawa, T.; Kurita, S.; Ueji, S.; Yamada, T.; Kuwata, S. Resolution of Mandelic Acids by Lipase-Catalyzed Transesterifications in Organic Media: Inversion of Enantioselectivity Mediated by the Acyl Donor. J. Chem. Soc., Perkin Trans. I 1992, 2253-2255.
57. Chadha, A.; Manohar, M. Enzymatic Resolution of 2-Hydroxy-4-phenylbutanoic Acid and 2-Hydroxy-4-phenylbutenoic Acid. Tetrahedron: Asymmetry 1995, 6, 651-652.
58. Matsumoto, K.; Suzuki, N.; Ohta, H. Preparation of Optically Active α-Hydroxy Ketone Derivatives by Enzyme-Mediated Hydrolysis of Enol Esters. Tetrahedron Lett. 1990, 37, 7159-7162.
59. Kalaritis, P.; Regenye, R. W.; Partridge, J. J.; Coffen, D. L. Kinetic Resolution of 2-Substituted Esters Catalyzed by a Lipase Ex. Pseudomonas fluorescens. J. Org. Chem. 1990, 55, 812-815.
60. Effenberger, F. Synthesis and Reactions of Optically Active Cyanohydrines. Angew. Chem., Int. Ed. Engl. 1994, 33, 1555-1565.
61. Effenberger, F.; Null, V.; Ziegler, T. Preparation of Optically Pure L-2-Hydroxyaldehydes with Yeast Transketolase. Tetrahedron Lett. 1992, 33, 5157-5160.