Lactobacillus curvatus Suşu ile Asetofenon Türevlerinin Asimetrik İndirgenmesi

Yıl 2017, Cilt: 7 Sayı: 2, 285 - 308, 31.07.2017

Engin Şahin

Öz

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.

Anahtar Kelimeler

Lactobacillus curvatus, Biyokatalizör, Enantioseçici indirgenme, Keton, Kiral alkol, Lactobacillus curvatus

Asymmetric Reduction of Acetophenone Derivatives by a Lactobacillus curvatus strain

Öz

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.

Anahtar Kelimeler

Biocatalyst, enantioselective reduction, ketone, chiral alcohol, Lactobacillus curvatus

Kaynakça

• 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.