(R)-1-Phenylethanol Production from Racemic 1- Phenylethanol by Double Strains Redox-Coupling

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Abstract:

A strain S307 that can oxidize selectively (S)- 1-phenylethanol to acetophenone and a strain IS 118 that can asymmetric reduce acetophenone to (R)- 1-phenylethanol were isolated from soil. S307 was identified as a species of Undibacterium belonging to the family Oxalobacteraceae of the Betaproteobacteria. S307. IS 118 was identified as Asperillus tamarii. The oxidation of (R, S)-1- phenylethanol with Undibacterium sp. S307 followed by the reduction of the oxidation mixture with Asperillus tamarii IS 118 to afford (R)-1-phenylethanol was described. The effects of redox-coupling patterns on the product of (R)-1-phenylethanol were investigated. After redox-coupling deracemization, the yield and ee of (R)-1-phenylethanol were 87% and 99% respectively.

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Advanced Materials Research (Volumes 236-238)

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981-985

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May 2011

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© 2011 Trans Tech Publications Ltd. All Rights Reserved

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[1] S. Shimizu, M. Kataoka, K. Kita. J Mol. Catal. B: Enzym, Vol. 5 (1998), p.321

Google Scholar

[2] J. A. R. Rodrigues, P. J. S. Moran, L. C. Fardelone, et al. Food Technol. Biotechnol., Vol. 42 (2004), p.295

Google Scholar

[3] R. Noyori. Asymmetric Catalysis in Organic Synthesis (John Wiley & Sons, Ltd, New York 1994)

Google Scholar

[4] G. Fantin, M. Fogagnolo, A. Medici, et al. Tetrahedron Lett. Vol. 36 (1995), p.441

Google Scholar

[5] Y Luo, Y. T. Zheng, Z. B. Jiang, Y. S. Ma, et al. App. Microb. Biotechnol. Vol. 73 (2006), p.349

Google Scholar

[6] R. Csuk, B. I. Glanzer, Chem. Rev. Vol. 91(1991), p.49

Google Scholar

[7] K. Nakamura, R. Yamanaka, T. Matsudab, et al. Tetrahedron: Asymmetry. Vol. 14 (2003), p.2659

Google Scholar

[8] X. Liu, Z. J. Fang, J. H. Xu, Chinese J. Catal. Vol. 27 (2006), p.20

Google Scholar

[9] D. Mandal, A. Ahmad, M. I. Khan, et al. J Mol. Catal. B: Enzym, Vol. 27 (2004), p.61

Google Scholar

[10] G. Fantin, M. Fogagnolo, P. P. Giovannini, et al. Tetrahedron: Asymmetry. Vol. 6 (1995), p.3047

Google Scholar

[11] Y. Xu, L. N. Zhang, J. H. Xu, Patent, CN 101016526

Google Scholar

[12] J. C. Andrew, Adv. Biochem. Eng./Biotech.. Vol. 63 (1999), p.57

Google Scholar

[13] K. Nakamura, Y. Inoue, T. Matsuda, J. Org. Chem. Vol. 63 (1998), p.8957

Google Scholar

[14] H. C. Brown, B. T. Cho, W. S. Park, J. Org. Chem. Vol. 53 (1988), p.1231

Google Scholar