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SHORT PUBLICATION

Enzyme-catalyzed asymmetric synthesis of optically active (R)- and (S)-ethyl -4-phenyl-4-hydroxybutyrate with microbial cells

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Pages 66-70 | Received 20 Jun 2012, Accepted 10 Dec 2012, Published online: 24 Jan 2013

References

  • Chen Y, Lie F, Li Z. 2009. Enantioselective benzylic hydroxylation with Pseudomonas monteilii TA-5: a simple method for synthesis of ®-benzylic alcohols containing reactive functional groups. Adv Synth Catal 351:2107–2112.
  • Chen Y, Lin H, Xis S, Wang L. 2008. Preparation the key intermediate of ACE inhibitors: high enantioselective production of ethyl (R)-2-hydroxy-4-phenylbutyrate with Candida boidinii CIOC21. Adv Synth Catal 350:426–430.
  • Chen Y, Tang W, Mou J, Li Z. 2010. High-throughput method for determining the enantioselectivity of biocatalyst for hydroxylation based on mass spectrometry. Angew. Chem Int Ed 122: 5278–5283.
  • Chen Y, Xu J, Lin H, Xia S. 2007. Enantiocomplementary preparation of (S)- and (R)-mandelic acid derivatives via α-hydroxylation of 2-arylacetic acid derivatives and reduction of α-Ketoester using microbial whole cells. Tetrahedron Asymmetry 18:2537–2540.
  • Corey EJ, Bakshi RK, Shibata S. 1987. A stable and easily prepared catalyst for the enantioselective reduction of ketones, applications to multistep syntheses. J Am Chem Soc 109: 7925–7926.
  • Corey EJ, Chen CP, Parry MJ. 1988. Dual binding modes to the receptor for platelet activating factor (PAF) of anti-paf trans-2,5-diarylfurans. Tetrahedron Lett 29:2899–2902.
  • Griebenow K, Vidal M, Baéz C, Santos AM, Barletta G. 2001. Nativelike enzyme properties are important for optimum activity in neat organic solvents. J Am Chem Soc 123:5380–5381.
  • Manzocchi A, Casati R, Fiecchi A, Santaniello E. 1987. Studies on the stereochemical control of fermenting baker's yeast mediated reductions: some 3- and 4-oxo esters. J Chem Soc Perkin Trans 1:2753–2757.
  • Matsuda T, Yamanaka R, Nakamura K. 2009. Recent progress in biocatalysis for asymmetric oxidation and reduction. Tetrahedron Asymmetry 20:513–557.
  • Militzer HC, Bosch B, Eckert M, Meseguer B. 2005. Process for stereoselectively reducing 4-aryl-4-oxobutanoic acid derivatives. US Patent 5936124.
  • Noyori R, Masato K, Takeshi O. 1992. Process for produc- ing optically active gamma-butyrolactone derivatives. EP 0478147A1.
  • Ramachandran PV, Pitre S, Brown HC. 2002. Selective reductions 59. Effective intramolecular asymmetric reductions of α-, β-, and γ-keto acids with diisopinocampheylborane and intermolecular asymmetric reductions of the corresponding esters with B-Chlorodiisopinocampheylborane,J Org Chem 67: 5315–5319.

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