Биохимические методы синтеза оптически активного пантолактона (обзор)
Автор: Миронова А.В., Гришко В.В., Ившина И.Б.
Журнал: Вестник Пермского университета. Серия: Биология @vestnik-psu-bio
Рубрика: Микробиоогия
Статья в выпуске: 6, 2005 года.
Бесплатный доступ
Рассмотрены биохимические методы, обеспечивающие эффективное разделение рацемического пантолактона с участием дегидрогеназ, лактонгидролаз, липаз, карбоксильных эстераз или целых клеток микроорганизмов. Обоснована перспективность использования актинобактерий рода Rhodococcus в качестве новых продуцентов гидролитических ферментов
Короткий адрес: https://sciup.org/147204360
IDR: 147204360
Список литературы Биохимические методы синтеза оптически активного пантолактона (обзор)
- Гришко В.В., Миронова А.В., Ившина И Б. Биокаталитическое разделение рацемического ацетата пантолактона с использованием целых клеток родококков//Катализ в промышленности. 2005. № 6.
- Коронелли Т.В. и др. Эстеразная активность углеводородокисляющих бактерий//Микробиология. 1986. Т. 55, вып. 5. С. 883-884.
- Akbutina F.A. et al.. Geminal dimethyl-substituted fimctionalized C4-synthons from pantolactone//Russian Journal of organic chemistry. 2001. V. 37, № 5. P. 695-699.
- Asxenzi P., Clementi E., Polticelli F. The Rhodococcus sp. cocaine esterase: a bacterial candidate for novel pharmacokinetic-based therapies for cocaine abuse II lUBMB Life. 2003. V. 55, № 7. P. 397-402.
- Asxenzi P., Clementi E., Polticelli F. The Rhodococcus sp. cocaine esterase: a bacterial candidate for novel pharmacokinetic-based therapies for cocaine abuse IIШВМВ Life. 2003. V. 55, № 7. P. 397-402.
- Baumann M, Hauer B.H., Bornscheuer U.T. Rapid screening of hydrolases for the enantioselective conversion of 'difficult-to-resolve' substrates II Tetrahedron: Asymmetry. 2000. V. 11, № 23. P. 4781-4790.
- Calmes M., Daunis J., Mai N. Asymmetric synthesis of a-amino acids via diastereoselective addition of (R)-pantolactone to their ketens II Tetrahedron: Asymmetry. 1997. V. 8, № 10. P. 1641-1648.
- Calmes M., Glot C, Marlines J. Investigation into the enantioselective protonation of enolate Schiff bases with (R)-panto]actone II Tetrahedron; Asymmetry. 2001. V. 12, № 1. P. 49-52.
- Diezi S. et al. Inversion of enantioselectivity in the hydrogenation of ketopantolactone on platinum modified by ether derivatives of cinchonidine II Tetrahedron: Asymmetry. 2003. V. 14, № n. p. 2573-2577.
- Douja N. et al. Heterogeneous diastereoselective hydrogenation of pyridine and corresponding enamine covalently bound to pantolactone II J. Mol. Catal. A: Chem. 2003. V. 210, № 2. P. 205-209.
- Effenberger F., Eichhorn J., Roos J. Enzyme catalyzed addition of hydrocyanic acid to substituted pivalaldehydes -a novel synthesis of (R)-panto lactone II Tetrahedron: Asymmetry. 1995. V. 6, № 1. P. 271-282.
- Gudelj M. et al. Novel Rhodococcus esterases by genetic engineering II J. Mol. Catal. B: Enzym. 1998. V. 5,Xo 1-4. P. 261-266.
- Kanoh N, Tomatsu A., Nishikawa T. Practical deracemization of NM-3, a synthetic angiogenesis inhibitor II Tetrahedron: Asymmetry. 2003. V. 14, № 10. P. 1251-1253.
- Haiighton L. et al. Enzymatic kinetic resolution of pantolactone: relevance to chiral auxiliary chemistry II Tetrahedron: Asymmetry. 2000. V. 11, № 8. P. 1697-1701.
- Kanoh N. et al. Practical deracemization of NM-3, a synthetic angiogenesis inhibitor II Tetrahedron: Asymmetry. 2003. V. 14, № 10. P. 1251-1253.
- Kataoka M. et al. Optical resolution of racemic pantoic acid through microbial stereoselective lactonization in an organic solvent/water two-phase system II Enzyme Microb. Technol. 1996. V. 19, № 4. P. 307-310.
- Kataoka M. et al. Lactonohydrolase-catalyzed optical resolution of pantoyl lactone: selection of a potent enzyme producer and optimization of culture and reaction conditions for practical resolution//Appl. Microbiol. Biotechnol. 1995. V. 44, № 3-4. P. 333-338.
- Kataoka М., Shimizu S., Yamada Н. Purification and characterization of a novel FMN-dependent enzyme. Membrane-bound L(-i-)-pantoyl lactone dehydrogenase from Nocardia asteroides II Eur. J. Biochem. 1992. V. 204, № 2. P. 799-806.
- Ogawa J., Shimizu S. Microbial enzymes: new industrial appUcations from traditional screening methods II Trends Biotechnol. 1999. V. 17, № 1. P. 13-21.
- Ogawa J., Xie S.-X., Shimizu S. Production of (R)-3-pentyn-2-ol through stereospecific hydrolysis of racemic 3-pentyn-2-ol esters with microbial enzymes//Appl. Microbiol. Biotechnol. 1999. V. 51, № l. p. 53-57.
- Overbeeke P.LA. et al. Biocatalytic synthesis of cyclopropanol from cyclopropyl methyl ketone using whole cells of Rhodococcus erythropolis II J. Mol. Catal. B: Enzym. 2003. V. 21, № 1-2. P. 51-53.
- Pogorevc M. et al. Novel carboxyl esterase preparations for the resolution of linalyl acetate II Monatsh. Chem. 2000. V. 131, № 6. P. 639-644.
- Reets. M. Т., Ruggeberg C. J. A screening system for enantioselective enzymes based on differential cell growth II Tefrahedron: Asymmetry. 2000. V. 11, №23. P. 4781-4790.
- Shimizu S. et al. One-step microbial conversion of a racemic mixture of pantoyl lactone to optically active D-(-)-pantoyl lactone II Appl. Environ. Microbiol. 1987. V. 53. P. 519.
- Shimizu S., Kataoka M. Optical resolution of pantolactone by a novel fimgal enzyme, Lactonohydrolase II Ann. N. Y. Acad. Sci. 1996. V. 799. P. 650-658.
- Shimizu S., Kataoka M. Structure, fimction, and application of microbial lactonases II Chimia. 1996. V. 50, №9. P. 409-410.
- Sunil V.P., Bhattacharyya A. Enantioselective synthesis of pantolactone analogues from an ephedrinederived morpholme-dione II Tetrahedron. 2003. V. 59, №18. P. 3275-3282.
- Upadhya T.T., Gurunath S., Sudalai A. A new and short enantioselective synthesis of (R)-pantolactone II Tetrahedron: Asymmetry. 1999. V. 10, № 15. P. 2899-2904.
- Y.-X. Tang et al. Kinetic resolution of DLpantolactone by immobilized Fusarium moniliforme SW-902 II Process Biochem. 2002. V. 38, № 4. P. 545-549.
Статья научная