Skip to main content
Log in

Enzymatic resolution of amino acid esters using ionic liquid N-ethyl pyridinium trifluoroacetate

  • Published:
Biotechnology Letters Aims and scope Submit manuscript

Abstract

A new ionic liquid, N-ethyl pyridinium trifluoroacetate, was used with a commercial protease to resolve N-acetyl amino acid esters in place of traditional organic solvents. Products with enantiomeric excess (ee) between 86–97% were obtained. These results show that with low concentration of this new ionic liquid, the enzymatic resolution can be increased considerably depending upon the substrate being used.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  • Chenault HK, Dahmer J, Whitesides G (1989) Kinetic resolution of unnatural and rarely occurring amino acids: enantioselective hydrolysis of N-acyl amino acids catalyzed by acylase I. J. Am. Chem. Soc. 111: 6354-6364.

    Google Scholar 

  • Erbeldinger M, Mesiano AJ, Russell AJ (2000) Enzymatic catalysis of formation of Z-aspartame in ionic liquid-an alternative to enzymatic catalysis in organic solvents. Biotechnol. Prog. 16: 1129-1131.

    Google Scholar 

  • Holbrey JD, Seddon KR (1999) The phase behaviour of 1-alkyl-3-methylimidazolium tetrafluoroborates; ionic liquids and ionic liquid crystals. J. Chem. Soc., Dalton Trans. 2133-2139.

  • Kim K-W, Song B, Choi M-Y, Kim M-J (2001) Biocatalysis in ionic liquids: markedly enhanced enantioselectivity of lipase. Org. Lett. 3: 1507-1509.

    Google Scholar 

  • Lau RM, van Rantwijk F, Seddon KR, Sheldon RA (2000) Lipasecatalyzed reactions in ionic liquids. Org. Lett. 2: 4189-4191.

    Google Scholar 

  • Lozano P, De Diego T, Carrié D, Vaultier M, Iborra JL (2001) Overstabilization of Candida antarctica lipase B by ionic liquids in ester synthesis. Biotech. Lett. 23: 1529-1533.

    Google Scholar 

  • Schofer SH, Kaftzik N, Wasserscheid P, Kragl U (2001) Enzyme catalysis in ionic liquids: lipase catalysed kinetic resolution of1-phenylethanol with improved enantioselectivity. Chem. Commun. 5: 425-426.

    Google Scholar 

  • Welton T (1999) Room-temperature ionic liquids. Solvents for synthesis and catalysis. Chem. Rev. 99: 2071–2083.

    Google Scholar 

  • Wu G, Zhao H, Luo RG, Wei W, Malhotra SV (2001) Chiral synthesis and enzymatic resolution of S-(—)-piperazine-2-carboxylic acid using enzyme alcalase. Enantiomer 6: 343–346.

    Google Scholar 

  • Zhao H, Robert GL, Dean W, Malhotra SV (2002) Concise synthesis and enzymatic resolution of L–(+)–homophenylalanine hydrochloride. Enantiomer 7: 1–3.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Zhao, H., Malhotra, S.V. Enzymatic resolution of amino acid esters using ionic liquid N-ethyl pyridinium trifluoroacetate. Biotechnology Letters 24, 1257–1259 (2002). https://doi.org/10.1023/A:1016205924504

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1016205924504

Navigation