Issue

Vol. 26 No. 24 (2014)

Copyright (c) 2014 Musa M. Musa

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

Enantiopure (S)-4-Phenyl-3-butyn-2-ol and (S)-1-Phenyl-2-butanol Through an Enzymatic Reduction

https://doi.org/10.14233/ajchem.2014.17456
Musa M. Musa
Department of Chemistry, King Fahd University of Petroleum and Minerals, Dhahran 31261, Kingdom of Saudi Arabia Corresponding author: Fax: +96 61 38604277; Tel: +96 61 38607343; E-mail: musam@kfupm.edu.sa

Corresponding Author(s) : Musa M. Musa

Asian Journal of Chemistry, Vol. 26 No. 24 (2014)

Abstract

This paper describes an enzymatic approach to producing (S)-4-phenyl-3-butyn-2-ol [(S)-3] and (S)-1-phenyl-2-butanol [(S)-4] from their corresponding ketones. W110A secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus (W110A TeSADH), a Prelog mutant of TeSADH, is used as a biocatalyst in this approach. The enantioselective reduction of a,b-alkynyl ketone 4-phenyl-3-butyn-2-one produced (S)-3 in an excellent yield and high levels of both chemo- and enantio-selectivities keeping the alkynyl moiety intact. The reduction of 1-phenyl-2-butanone (2) produced (S)-4 of higher enantioselectivity than that observed previously in the W110A TeSADH-catalyzed reduction of phenylacetone, a ketone with one methylene unit less than compound 2.

Keywords

Alcohol dehydrogenase Asymmetric reduction Biotransformations (S)-1-Phenyl-2-butanol (S)-4-Phenyl-3-butyn-2-ol.
M. Musa, M. (2014). Enantiopure (S)-4-Phenyl-3-butyn-2-ol and (S)-1-Phenyl-2-butanol Through an Enzymatic Reduction. Asian Journal of Chemistry, 26(24), 8363–8365. https://doi.org/10.14233/ajchem.2014.17456
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX
References
  1. (a) K. Faber, Biotransformations in Organic Chemistry, edn. 6, Springer, Heidelberg (2011); (b) F. Hollmann, I.W.C.E. Arends and D. Holtmann, Green Chem., 13, 2285 (2011).
  2. U.T. Bornscheuer, G.W. Huisman, R.J. Kazlauskas, S. Lutz, J.C. Moore and K. Robins, Nature, 485, 185 (2012).
  3. E. Garcia-Urdiales, I. Alfonso and V. Gotor, Chem. Rev., 111, PR110 (2011).
  4. Y. Ni and J.-H. Xu, Biotechnol. Adv., 30, 1279 (2012).
  5. M.M. Musa and R.S. Phillips, Catal. Sci. Technol., 1, 1311 (2011).
  6. D.S. Burdette, V.V. Tchernajencko and J.G. Zeikus, Enzyme Microb. Technol., 27, 11 (2000).
  7. K.I. Ziegelmann-Fjeld, M.M. Musa, R.S. Phillips, J.G. Zeikus and C. Vieille, Protein Eng. Des. Sel., 20, 47 (2007).
  8. V. Prelog, Pure Appl. Chem., 9, 119 (1964).
  9. K. Nakamura, K. Takenaka and A. Ohno, Tetrahedron Asymm., 9, 4429 (1998).
  10. V.K. Yadav and K. Ganesh Babu, Tetrahedron, 59, 9111 (2003).
  11. M.M. Musa, R.S. Phillips, M. Laivenieks, C. Vieille, M. Takahashi and S.M. Hamdan, Org. Biomol. Chem., 11, 2911 (2013).
  12. T. Schubert, W. Hummel, M.-R. Kula and M. Müller, Eur. J. Org. Chem., 2001, 4181 (2001).
  13. A. Uzura, T. Katsuragi and Y. Tani, J. Biosci. Bioeng., 92, 381 (2001).
  14. K. Matsumura, S. Hashiguchi, T. Ikariya and R. Noyori, J. Am. Chem. Soc., 119, 8738 (1997).
  15. Z. Zhang, P. Jain and J.C. Antilla, Angew. Chem. Int. Ed., 50, 10961 (2011).
  16. S. Eagon, C. DeLieto, W.J. McDonald, D. Haddenham, J. Saavedra, J. Kim and B. Singaram, J. Org. Chem., 75, 7717 (2010).
  17. M.M. Musa, K.I. Ziegelmann-Fjeld, C. Vieille, J.G. Zeikus and R.S. Phillips, J. Org. Chem., 72, 30 (2007).
  18. E. Keinan, E.K. Hafeli, K.K. Seth and R. Lamed, J. Am. Chem. Soc., 108, 162 (1986).
  19. TeSADH and TbADH are identical, See: M.M. Musa, K.I. Ziegelmann-Fjeld, C. Vieille, J.G. Zeikus and R.S. Phillips, Angew. Chem. Int. Ed., 46, 3091 (2007).
Read More
Author biographies is not available.
Download
Statistic
Read Counter : 0