Synthesis of (R)-(-)-Mandelic Acid Ethyl Ester by Asymmetric Reduction of Ethyl Benzoylformate with Yeast Cells

Zhi Min Ou; Ying Kang Nan

doi:10.4028/www.scientific.net/AMR.560-561.273

Paper Titles

Qⁿ Distribution in Silicates: Alkali Silicate Glasses and Melts
p.254

Preparation of Precursor of LiNi_0.5Mn_1.5O₄ with High Density by Two-Dryness Co-Precipitation Method
p.259

Effect of Synthesis Time on Microscopic Characteristics of 12CaO·7Al₂O₃
p.263

Preparation of Carbon Micro-Spheres from Liquefaction Products of Lignite with NaOH-Methanol
p.267

Synthesis of (R)-(-)-Mandelic Acid Ethyl Ester by Asymmetric Reduction of Ethyl Benzoylformate with Yeast Cells
p.273

Hierarchical Control Based Virtual Coordinated Synchronization of Chemical Auto Catalytic Reaction Networks
p.279

Preparation, Characterization of Co₃O₄ Nano-Particles and its Catalytic Effect on the Combustion of Fuel Rich Propellants
p.284

Preparation of Pt-Sn-K/Al₂O₃ Catalysts and its Catalytic Performance in Propane Dehydrogenation
p.289

One-Pot Synthesis of 1-Benzoylpyrene over Heteropoly Acid Catalysts
p.294

HomeAdvanced Materials ResearchAdvanced Materials Research Vols. 560-561Synthesis of (R)-(-)-Mandelic Acid Ethyl Ester by...

Synthesis of (R)-(-)-Mandelic Acid Ethyl Ester by Asymmetric Reduction of Ethyl Benzoylformate with Yeast Cells

Abstract:

An efficient yeast cell biotransformation process was set up for asymmetric synthesis of (R)-(-)-mandelic acid ethyl ester, a key drug intermediate. Saccharomyces cerevisiae 21 was selected as optimum strain for biotransformation. The optimum reduction conditions are as follows: substrate concentration 20 g/L, cell concentration 140 g/L, reaction time 36 h, temperature 30 0C. Conversion and enantiometric excess of (R)-(-)-mandelic acid ethyl ester reached 99.8 % and 100%.

You might also be interested in these eBooks

View Preview

Info:

Periodical:

Advanced Materials Research (Volumes 560-561)

Pages:

273-278

DOI:

https://doi.org/10.4028/www.scientific.net/AMR.560-561.273

Citation:

Cite this paper

Online since:

August 2012

Authors:

Zhi Min Ou, Ying Kang Nan

Keywords:

(R)-(-)-Mandelic Acid Ethyl Ester, Asymmetric Reduction, Biotransformation, Ethyl Benzoylformate

Export:

RIS, BibTeX

Price:

Permissions:

Request Permissions

References

[1] S. Oda, Y. Inada, A. Kobayashi, H. Ohta, Production of ethyl (R)-2-hydroxy-4-phenylbutanoate via reduction of ethyl 2-oxo-4-phenylbutanoate in an interface bioreactor, Biosci. Biotechnol .Biochem. 62 (1998) 1762-1767.

DOI: 10.1271/bbb.62.1762

Google Scholar

[2] P. Sarananan, V.K. Singh, An efficient synthesis of chiral nonracemic diamines:application in asymmetric cynthesis, Tetrabedron Lett. 39 (1998) 167-170.

DOI: 10.1016/s0040-4039(97)10578-0

Google Scholar

[3] R. Noyori, Asymmetric Catalysis: Science and Opportunities (Nobel Lecture 2001), Adv. Synth. Catal. 345 (2003) 15-32.

DOI: 10.1002/adsc.200390002

Google Scholar

[4] E.J. Ariëns, Nonchiral, homochiral and composite chiral drugs, Trends Pharmacol. Sci. 14 (1993) 68-75.

DOI: 10.1016/0165-6147(93)90033-g

Google Scholar

[5] J.M. Palomo, G. Fernandez-Lorente, C. Ortiz, R. Fernandez-Lafuente, J.M. Guisan, Modulation of the enantioselectivity of lipases via controlled immobilization and medium engineering: hydrolytic resolution of mandelic acid esters, Enzyme Microb. Technol. 31 (2002) 775-783.

DOI: 10.1016/s0141-0229(02)00169-2

Google Scholar

[6] D.Y. Ganapati, P. Sivakumar, Enzyme-catalysed optical resolution of mandelic acid via RS (∓) -methyl mandelate in non-aqueous media, Biochem. Eng. J. 19 (2004) 101-107.

DOI: 10.1016/j.bej.2003.12.004

Google Scholar

[7] M.D. Lilly, Advances in biotransformation processes, Chem. Eng. Sci. 49 (1994) 151-159.

Google Scholar

[8] R.N. Patel, Biocatalytic synthesis of intermediates for the synthesis of chiral drug substances, Curr. Opin. Biotechnol. 12 (2001) 587-604.

DOI: 10.1016/s0958-1669(01)00266-x

Google Scholar

[9] K. Nakamura, Y. Kawai, N. Nakajima, A. Ohno, Stereochemical control of microbial reduction 17: a method for controlling the enantioselectivity of reductions with Bakers'Yeast, Org. Chem. 56 (1991) 4778-4783.

DOI: 10.1021/jo00015a038

Google Scholar