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Lactobacillus curvatus Suşu ile Asetofenon Türevlerinin Asimetrik İndirgenmesi

Year 2017, Volume: 7 Issue: 2, 285 - 308, 31.07.2017

Abstract

Sekiz farklı Lactobacillus curvatus suşu asetofenon’un 1-fenil etanol’e
asimetrik indirgenmesinde biyokatalizör olarak değerlendirildi. Test edilen bu
laktik asit bakteri (LAB) suşları arasında Lactobacillus
curvatus
N5 asetofenon’un enantiyoseçici indirgenmesinde en etkili biyokatalizör
olarak bulundu. Optimize edilen reaksiyon şartları altında asetofenon türevleri
% 99 enantiyomerik fazlalığa kadar ilgili kiral sekonder alkollere dönüştürüldü.

References

  • Kataoka, M., Kita, K., Ada, M., Yasohara, Y., Hasegawa, J. ve Shimuzu, S., 2003, Novel bioreduction system for the production of chiral alcohols. Appl. Microbial. Biotechnol., 62, 437-445.
  • Wong, C. H., Drueckhammer, D. G. ve Sweers, H. M., 1985, Enyzmatic vs. fermentative synthesis: thermostable clucose dehydrogenase catalyzed regeneration of NADPH for use in enzymatic synthesis, J. Am. Chem. Soc., 107, 4028-4031.
  • Bruni, R., Fantin, G., Maietti, S., Medici, A., Pedrini, P. ve Sacchetti, G., 2006, Asymmetric reduction of ketones by employing Rhodotorula sp. AS2.2241 and synthesis of the β-blocker (R)-nifenalol, Tetrahedron: Asymmetry, 17, 1769-1774.
  • Mandal, D., Ahmat, A., Khan, M. I. ve Kumar, R., 2004, Enantioselective bioreduction of acetophenone and its analogous by the fungus Trichothecium, J. Mol, Catal. B: Enzym, 27, 61-63.
  • Faber, K., 1997, Biotranformations in Organic Chemistry, Springer Press, Berlin, Germany, 10–16p.
  • Faber, K., 2000, Biocatalytic Application. In biotranformations in Organic Chemistry, Springer Press, Berlin, Germany, 192–193p.
  • 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, 25-64.
  • Wei, S. ve Du, H., 2014, A Highly Enantioselective Hydrogenation of Silyl Enol Ethers Catalyzed by Chiral Frustrated Lewis Pairs, J. Am. Chem. Soc., 136, 12261-12264.
  • Zhang, Z., Jain, P. ve Antilla, J. C., 2011, Asymmetric Reduction of Ketones by Phosphoric Acid Derived Catalysts, Agew. Chem. Int. Ed., 50, 10961-20964
  • Li, Y., Yu, S., Wu, X., Xiao, J., Shen, W., Dong, Z.ve Gao, J., 2014, Iron Catalyzed Asymmetric Hydrogenation of Ketones, J. Am. Chem. Soc.,136, 4031-4039.
  • Vieira, G. A. B., Araujo, D. M. F., Lemos, T. L. G., Mattos, M. C., Oliveira, M. C. F., Melo, V.M. M., Gonzalu, G., Gotor-Fernandez, V. ve Gotor, V., 2010, Candida tropicalis CE017: A new Brazilian Enzymatic Source for the Bioreduction of Aromatic Prochiral Ketones, J. Braz. Chem. Soc., 21, 1-21.
  • Liu, W. P., Yuan, M. L., Yang, X. H., Li, K., Xie, J. H. ve Zhou, Q. L., 2015, Efficient asymmetric transfer hydrogenation of ketones in ethanol with chiral iridium complexes of spiro PAP ligands as catalysts, Chem. Commun., 51, 6123-6125.
  • Singh, A. ve Chopra, H. K., 2016, New benzimidazolium-based chiral ionic liquids: synthesis and application in enantioselective sodium borohydride reductions in water, Tetrahedron: Asymmetry., 27, 448-453.
  • Wakeham, R. J., Morris, J. A. ve Williams, M. J., 2015, Alternative Hydrogen Source for Asymmetric Transfer Hydrogenation in the Reduction of Ketones, Chemcatchem., 7, 4039-4041.
  • Zilbeyaz, K., Kilic, H., Sisecioğlu, M., Özdemir, H. ve Güngör, A. A., 2012, Preparation of enantiomerically pure p-substituted phenylethyl hydroperoxides by kinetic resolution and their use as enantioselective oxidants in the asymmetric Weitz–Scheffer epoxidation of E-chalcone, Tetrahedron: Asymmetry, 23, 594-601.
  • Ren, X., Wei, S. ve Du, H, 2015, A Facile Development of Chiral Alkenyl boranes from Chiral Diynes for Asymmetric Hydrogenation of Silyl Enol Ethers, Org. Lett., 17, 990-993.
  • Dertli, E., Mercan, E., Arıcı, M., Yılmaz, M. T., ve Sağdıç, O, 2016. Characterisation of lactic acid bacteria from Turkish sourdough and determination of their exopolysaccharide (EPS) production characteristics. LWT-Food Science and Technology, 71, 116-124.

Asymmetric Reduction of Acetophenone Derivatives by a Lactobacillus curvatus strain

Year 2017, Volume: 7 Issue: 2, 285 - 308, 31.07.2017

Abstract

Eight strains of Lactobacillus
curvatus
were evaluated as biocatalysts in the
asymmetric reduction of acetophenone to 1-phenyl ethanol. Among the tested lactic
acid bacteria (LAB) strains
Lactobacillus curvatus N5 was found to be an effective biocatalyst for the
enantioselective reduction of acetophenone. Under the optimized reaction
conditions, derivatives of acetophenones were converted to the corresponding
chiral secondary alcohols in up to 99% enantiomeric excess.

References

  • Kataoka, M., Kita, K., Ada, M., Yasohara, Y., Hasegawa, J. ve Shimuzu, S., 2003, Novel bioreduction system for the production of chiral alcohols. Appl. Microbial. Biotechnol., 62, 437-445.
  • Wong, C. H., Drueckhammer, D. G. ve Sweers, H. M., 1985, Enyzmatic vs. fermentative synthesis: thermostable clucose dehydrogenase catalyzed regeneration of NADPH for use in enzymatic synthesis, J. Am. Chem. Soc., 107, 4028-4031.
  • Bruni, R., Fantin, G., Maietti, S., Medici, A., Pedrini, P. ve Sacchetti, G., 2006, Asymmetric reduction of ketones by employing Rhodotorula sp. AS2.2241 and synthesis of the β-blocker (R)-nifenalol, Tetrahedron: Asymmetry, 17, 1769-1774.
  • Mandal, D., Ahmat, A., Khan, M. I. ve Kumar, R., 2004, Enantioselective bioreduction of acetophenone and its analogous by the fungus Trichothecium, J. Mol, Catal. B: Enzym, 27, 61-63.
  • Faber, K., 1997, Biotranformations in Organic Chemistry, Springer Press, Berlin, Germany, 10–16p.
  • Faber, K., 2000, Biocatalytic Application. In biotranformations in Organic Chemistry, Springer Press, Berlin, Germany, 192–193p.
  • 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, 25-64.
  • Wei, S. ve Du, H., 2014, A Highly Enantioselective Hydrogenation of Silyl Enol Ethers Catalyzed by Chiral Frustrated Lewis Pairs, J. Am. Chem. Soc., 136, 12261-12264.
  • Zhang, Z., Jain, P. ve Antilla, J. C., 2011, Asymmetric Reduction of Ketones by Phosphoric Acid Derived Catalysts, Agew. Chem. Int. Ed., 50, 10961-20964
  • Li, Y., Yu, S., Wu, X., Xiao, J., Shen, W., Dong, Z.ve Gao, J., 2014, Iron Catalyzed Asymmetric Hydrogenation of Ketones, J. Am. Chem. Soc.,136, 4031-4039.
  • Vieira, G. A. B., Araujo, D. M. F., Lemos, T. L. G., Mattos, M. C., Oliveira, M. C. F., Melo, V.M. M., Gonzalu, G., Gotor-Fernandez, V. ve Gotor, V., 2010, Candida tropicalis CE017: A new Brazilian Enzymatic Source for the Bioreduction of Aromatic Prochiral Ketones, J. Braz. Chem. Soc., 21, 1-21.
  • Liu, W. P., Yuan, M. L., Yang, X. H., Li, K., Xie, J. H. ve Zhou, Q. L., 2015, Efficient asymmetric transfer hydrogenation of ketones in ethanol with chiral iridium complexes of spiro PAP ligands as catalysts, Chem. Commun., 51, 6123-6125.
  • Singh, A. ve Chopra, H. K., 2016, New benzimidazolium-based chiral ionic liquids: synthesis and application in enantioselective sodium borohydride reductions in water, Tetrahedron: Asymmetry., 27, 448-453.
  • Wakeham, R. J., Morris, J. A. ve Williams, M. J., 2015, Alternative Hydrogen Source for Asymmetric Transfer Hydrogenation in the Reduction of Ketones, Chemcatchem., 7, 4039-4041.
  • Zilbeyaz, K., Kilic, H., Sisecioğlu, M., Özdemir, H. ve Güngör, A. A., 2012, Preparation of enantiomerically pure p-substituted phenylethyl hydroperoxides by kinetic resolution and their use as enantioselective oxidants in the asymmetric Weitz–Scheffer epoxidation of E-chalcone, Tetrahedron: Asymmetry, 23, 594-601.
  • Ren, X., Wei, S. ve Du, H, 2015, A Facile Development of Chiral Alkenyl boranes from Chiral Diynes for Asymmetric Hydrogenation of Silyl Enol Ethers, Org. Lett., 17, 990-993.
  • Dertli, E., Mercan, E., Arıcı, M., Yılmaz, M. T., ve Sağdıç, O, 2016. Characterisation of lactic acid bacteria from Turkish sourdough and determination of their exopolysaccharide (EPS) production characteristics. LWT-Food Science and Technology, 71, 116-124.
There are 17 citations in total.

Details

Subjects Engineering
Journal Section Articles
Authors

Engin Şahin

Publication Date July 31, 2017
Submission Date March 29, 2017
Acceptance Date July 20, 2017
Published in Issue Year 2017 Volume: 7 Issue: 2

Cite

APA Şahin, E. (2017). Lactobacillus curvatus Suşu ile Asetofenon Türevlerinin Asimetrik İndirgenmesi. Gümüşhane Üniversitesi Fen Bilimleri Dergisi, 7(2), 285-308.