Asymmetric Reduction of Prochiral Ketones to Chiral Alcohol by Photo-Biocatalysis with Microalgae

Abstract:

The photo-biocatalytic ability of eukaryotic microalgae and prokaryotic microalgae on nonnatural prochiral ketones to produce chiral alcohols was studied in this paper. The results proved that ethyl acetoacetate and acetophenone can be stereo-selectively reduced to the corresponding ethyl S-3-hydroxybutyrate (EHB) and S-1-phenylethanol (PEA) by microalgal photo-biocatalysis with high enantioselectivity, respectively. Scenedesmus obliquus has the best photo-biocatalytic activity to ethyl acetoacetate reduction reaction among the two selected eukaryotic microalgae, about 43.98% yield and 69.58% e.e. achieved. Spirulina platensis is the best biocatalyst to acetophenone among the four selected prokaryotic microalgae, about 52.65% yield and 99.40% e.e. achieved.

• Periodical: Advanced Materials Research (Volume 803)
• Pages: 60-63
• DOI: https://doi.org/10.4028/www.scientific.net/AMR.803.60
• Online since: September 2013
• Authors: Geng Hua Chen, Sen Xiang Zhang, Qiao Hu, Xin Xing Deng, Fang Yu, Zhong Hua Yang, Ya Li Hou
• Keywords: Asymmetric Reduction, Chiral Alcohols, Microalgae, Photo-Biocatalysis

References

[1] T. Matsuda, R. Yamanaka and K. Nakamura: Tetrahedron: Asymmetry, Vol. 20(2009), p.513.

[2] J.Y. Houng and J.S. Liau: Enzyme and Microbial Technology, Vol. 38(2006), p.879.

[3] M.L. Wang, R. Hu, X.L. Guo, F.K. Yan and D.S. Liu. Chinese Journal of Catalysis: Vol. 29(2008) No. 3, p.233. In Chinese.

[4] A. Vandenberghe, I.E. Marko, F. Lucaccioni and S. Lutts: Industrial Crops and Products, Vol. 42 (2013), p.380.

[5] K. Ishihara, N. Nakajima, H. Yamaguchi, H. Hamadad and Y. Uchimura: Journal of Molecular Catalysis B: Enzymatic, Vol. 15 (2001), p.101.

[6] K. Itoh, H. Sakamaki, K. Nakamura and C.A. Horiuchi: Tetrahedron: Asymmetry, Vol. 16(2005), p.1403.

[7] F. Yoshizako, T. Kuramoto, A. Nishimura and M. Chubachi: Journal of Fermentation and Bioengineering, Vol. 85(1998) No. 4, p.439.

DOI: 10.1016/s0922-338x(98)80091-3

[8] Z.H. Yang, L. Luo, X. Chang, W. Zhou, G.H. Chen, Y. Zhao and Y.J. Wang: Journal of Industrial Microbiology & Biotechnology, Vol. 39(2012), p.835.

[9] Z.H. Yang and S.J. Yao: Chinese Journal of Catalysis, Vol. 25(2004), No. 6, p.434. In Chinese.

[10] J.Y. Wang, S.G. Zhu and C.F. Xu: Biochemistry (Higher Education Press, China 2002) , p.208.

[11] K. Nakamura and R. Yamanaka: Tetrahedron: Asymmetry, Vol. 13 (2002), p.2529.