Skip to main content
SpringerLink
Log in

Fatty and aromatic acids as acyl donors in enzymatic kinetic resolution of phenylethanol and 1-phenylpropan-2-ol

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

The use of fatty and aromatic acids as green acyl donors for enzymatic kinetic resolution via esterification of 1-phenylethanol and 1-phenylpropan-2-ol was described. The impact of the presence of magnesium sulfate on both reactivity and selectivity of Candida rugosa lipase (CRL) was checked. The organic solvents, the medium dilution, and the temperature revealed as determinant parameters to achieve enantioselective esterification reactions. A significant impact of the use of magnesium sulfate was revealed on the enantioselectivity of the CRL in heptane during the resolution of 1-phenylethanol, using butyric and lauric acids as acyl donors.

Graphical abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1

Similar content being viewed by others

Data availability

The authors confirm that all data supporting this article is available within the main manuscript and the supporting information.

References

  1. Gerlach D, Schreier P (1989) Biocatalysis 2:257

    Article  CAS  Google Scholar 

  2. Chua LS, Sarmidi MR (2006) Enzyme Microb Technol 38:551

    Article  CAS  Google Scholar 

  3. Karadeniz F, Bayraktar E, Mehmetoglu Ü (2010) Artif Cells, Blood Substitutes Biotechnol 38:288

    Article  CAS  Google Scholar 

  4. Paravidino M, Hanefeld U (2011) Green Chem 13:2651

    Article  CAS  Google Scholar 

  5. Sikora A, Siódmiak T, Marszałł MP (2014) Chirality 26:663

    Article  CAS  PubMed  Google Scholar 

  6. Brodzka A, Koszelewski D, Zysk M, Ostaszewski R (2018) Catal Commun 106:82

    Article  CAS  Google Scholar 

  7. Ali SH, Tarakmah A, Merchant SQ, Al-Sahhaf T (2007) Chem Eng Sci 62:3197

    Article  CAS  Google Scholar 

  8. Fan C, Wan R, Kong P, Wang X, Wang J, Zhang X, Zheng Z (2020) Catal Commun 140:106002

    Article  CAS  Google Scholar 

  9. Khan Z, Javed F, Shamair Z, Hafeez A, Fazal T, Aslam A, Rehman F (2021) J Ind Eng Chem 103:80

    Article  CAS  Google Scholar 

  10. Laboret F, Perraud R (1999) Appl Biochem Biotechnol 82:185

    Article  CAS  PubMed  Google Scholar 

  11. Alvarez E, Rodriguez J, Villa R, Gomez C, Nieto S, Donaire A, Lozano P (2019) ACS Sustainable Chem Eng 7:13307

    Article  CAS  Google Scholar 

  12. Bayout I, Bouzemi N, Guo N, Mao X, Serra S, Riva S, Secundo F (2020) Flavour Fragrance J 35:209

    Article  CAS  Google Scholar 

  13. Gamayurova VS, Zinoveva ME, Shnaider KL, Davletshina GA (2021) Catal Ind 13:58

    Article  Google Scholar 

  14. Chua LS, Sarmidi M (2004) J Mol Catal B: Enzym 28:111

    Article  CAS  Google Scholar 

  15. Vanin AB, Orlando T, Piazza SP, Puton BM, Cansian RL, Oliveira D, Paroul N (2014) Appl Biochem Biotechnol 174:1286

    Article  CAS  PubMed  Google Scholar 

  16. Lortie R (1997) Biotechnol Adv 15:1

    Article  CAS  PubMed  Google Scholar 

  17. Zieniuk B, Fabiszewska A, Wołoszynowska M, Białecka-Florjańczyk E (2021) Biocatal Biotransform 39:455

    Article  CAS  Google Scholar 

  18. Bôas V, de Castro HF (2021) Biotechnol Bioeng 119:725

    Article  Google Scholar 

  19. Irimescu R, Saito T, Kato K (2003) J Am Oil Chem Soc 80:659

    Article  CAS  Google Scholar 

  20. Gawas SD, Jadhav SV, Rathod VK (2016) App Biochem Biotechnol 180:1428

    Article  CAS  Google Scholar 

  21. Cea M, González ME, Abarzúa M, Navia R (2019) J Environ Manage 242:171

    Article  CAS  PubMed  Google Scholar 

  22. Hari Krishna S, Karanth NG (2007) Catal Rev 44:499

    Article  Google Scholar 

  23. Faber K (2011) Biotransformations in Organic Chemistry, 6th edn. Springer-Verlag, Berlin

    Book  Google Scholar 

  24. Simić S, Zukić E, Schmermund L, Faber K, Winkler CK, Kroutil W (2021) Chem Rev 122:1052

  25. Merabet-Khelassi M, Aribi-Zouioueche L, Riant O (2008) Tetrahedron 19:2378

    Article  CAS  Google Scholar 

  26. Merabet-Khelassi M, Bouzemi N, Fiaud JC, Riant O, Aribi-Zouioueche L (2011) C R Chim 14:978

    Article  CAS  Google Scholar 

  27. Stergiou PY, Foukis A, Filippou M, Koukouritaki M, Parapouli M, Theodorou LG, Hatziloukas E, Afendra A, Pandey A, Papamichael EM (2013) Biotechnol Adv 31:1846

    Article  CAS  PubMed  Google Scholar 

  28. Lajtai-Szabó P, Nemestóthy N, Gubicza L (2020) Hung J Ind Chem 48:9

    Article  Google Scholar 

  29. Bezbradica D, Crovic MJ, Tanaskovic S, Lukovic N, Carevic M, Milivojevic A, Knezevic-Jugovic Z (2017) Curr Org Chem 21:104

    Article  CAS  Google Scholar 

  30. Duan Y, Du Z, Yao Y, Li R, Wu D (2006) J Agric Food Chem 54:6219

    Article  CAS  PubMed  Google Scholar 

  31. Silva GS, Santos JC, Oliveira PC, De Castro HF (2011) Eur Food Res Technol 233:743

    Article  Google Scholar 

  32. Findrik Z, Németh G, Vasić-Rački Đ, Bélafi-Bakó K, Csanádi Z, Gubicza L (2012) Proc Biochem 47:1715

    Article  CAS  Google Scholar 

  33. Freitas L, Zieniuk B, Groborz K, Wołoszynowska M, Ratusz K, Białecka-Florjańczyk E, Fabiszewska A (2021) Biomolecules 11:314

    Article  Google Scholar 

  34. Benamara NE, Merabet-Khelassi M, Lakoud SG, Aribi-Zouioueche L, Riant O (2021) ChemistrySelect 6:13941

    Article  CAS  Google Scholar 

  35. Kagan HB, Fiaud JC (1988) Kinetic Resolution. In: Eliel EL, Wilen SH (eds), Topics in Stereochemistry, vol 18. Wiley & Sons, New York

  36. Chen CS, Fujimoto Y, Sih CJ (1982) J Am Chem Soc 104:7294

    Article  CAS  Google Scholar 

  37. Hayashi T, Matsumoto Y (1991) Tetrahedron 2:601

    Article  CAS  Google Scholar 

  38. Naemura K, Murata M, Tanaka R, Yano M, Hirose K, Tobe Y (1996) Tetrahedron 7:1581

    Article  CAS  Google Scholar 

  39. Naemura K, Murata M, Tanaka R, Yano M, Hirose K, Tobe Y (1996) Tetrahedron 7:3285

    Article  CAS  Google Scholar 

  40. Kazlauskas RJ, Weissfloch AN, Rappaport AT, Cuccia LA (1991) J Org Chem 56:2656

    Article  CAS  Google Scholar 

  41. Okamoto T, Ueji S (2000) Biotechnol Lett 22:1169

    Article  CAS  Google Scholar 

  42. Salgin S, Takaç S (2007) Chem Eng Technol 30:1739

    Article  CAS  Google Scholar 

  43. Cowan JA (2002) Biometals 15:225

    Article  CAS  PubMed  Google Scholar 

  44. Tran-Ha MH, Santos V, Wiley DE (2005) J Membrane Sci 251:179

    Article  CAS  Google Scholar 

  45. Merabet-Khelassi M, Houiene Z, Aribi-Zouioueche L, Riant O (2012) Tetrahedron 23:828

    Article  CAS  Google Scholar 

  46. Frings K, Koch K, Hatmeier W (1999) Enzyme Microb Technol 25:303

    Article  CAS  Google Scholar 

  47. Ottoson J, Hult K (2001) J Mol Catal B 11:1025

    Article  Google Scholar 

  48. Suan C, Sarmidi MR (2004) J Mol Catal B 28:111

    Article  Google Scholar 

  49. Janssen AE, Vaidya AM, Halling PJ (1996) Enz Microb Technol 18:340

    Article  CAS  Google Scholar 

  50. Pleiss J, Fischer M, Schmid RD (1998) Chem Phys Lipids 93:67

    Article  CAS  PubMed  Google Scholar 

  51. Razi S, Zeror S, Merabet-Khelassi M, Kolodziej E, Toffano M, Aribi-Zouioueche L (2021) Catal Lett 151:2603

    Article  CAS  Google Scholar 

  52. Melais N, Aribi-Zouioueche L, Riant O (2016) C R Chimie 19:971

    Article  CAS  Google Scholar 

Download references

Acknowledgements

Algerian Ministry of Higher Education and Scientific Research (MESRS, FNR 2000) and ANDRU (PNR) are gratefully acknowledged for the financial support of this work.

Author information

Authors and Affiliations

  1. Ecocompatible Asymmetric Catalysis Laboratory, Badji Mokhtar Annaba-University, B.P 12, 23000, Annaba, Algeria

    Fatma Zohra Smaine, Mounia Merabet-Khelassi, Saoussen Zeror & Louisa Aribi-Zouioueche

  2. Equipe de Catalyse Moléculaire-ICMMO Bât 420, Université Paris-Sud, 91405, Paris Saclay, Orsay cedex, France

    Emilie Kolodziej & Martial Toffano

Authors
  1. Fatma Zohra Smaine
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Mounia Merabet-Khelassi
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Saoussen Zeror
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Emilie Kolodziej
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Martial Toffano
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Louisa Aribi-Zouioueche
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Saoussen Zeror.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (DOCX 2109 KB)

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Smaine, F.Z., Merabet-Khelassi, M., Zeror, S. et al. Fatty and aromatic acids as acyl donors in enzymatic kinetic resolution of phenylethanol and 1-phenylpropan-2-ol. Monatsh Chem 155, 105–113 (2024). https://doi.org/10.1007/s00706-023-03147-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-023-03147-3

Keywords

Search

Navigation