Log in

Kinetic resolution of heptan-2-ol-enantiomers by lipase-catalysed esteriîication in organic solvent

Lipase-katalysierte Veresterung von Heptan-2-ol durch Trennung der Enantiomere in organischem Lösungsmittel

  • Original Papers
  • Published:
Zeitschrift für Lebensmittel-Untersuchung und Forschung Aims and scope Submit manuscript

Zusammenfassung

Die Lipase-katalysierte Veresterung von racemischen Heptan-2-ol in organischem Lögsmittel wurde untersucht. Ausgehend von Buttersäure und (R,S)-Heptan-2-ol katalysiert in Heptan suspendierte Schweinepankreas-Lipase bevorzugt die Bildung von (R)-Buttersäure-2-heptylester. Die quantitative Verteilung der Produkte und der stereochemische Verlauf der Reaktion wurde mittels capillargaschromatographischer Methoden untersucht.

Summary

The lipase-catalysed esterification of racemic heptan-2-ol in organic solvent has been investigated. Porcine pancreas lipase, suspended in heptane, preferentially catalyses the synthesis of (R)-2heptyl butyrate starting from (R,S)-heptan-2-ol and butyric acid. The distribution of the reaction products and the stereochemical course of the esterification have been investigated by means of capillary gas chromatographic methods.

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

Access this article

Subscribe and save

Springer+ Basic
EUR 32.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or Ebook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

Price includes VAT (Germany)

Instant access to the full article PDF.

References

  1. Maarse H, Viissher CA (1984) Volatile compounds in food - Qualitative data. CIVO-TNO, Zeist

    Google Scholar 

  2. Engel K-H, Tressl R (1983) Chem Mikrobiol Technol Lebensm 8:33–39

    Google Scholar 

  3. Tressl R, Engel K-H (1985) Biogenesis of chiral aroma components and their analytical characterization at trace level. In: Adda J (ed) Progress in flavour research 1984. Elsevier, Amsterdam, pp 441–455

    Google Scholar 

  4. Mosandl A, Deger W (1987) Z Lebensm Unters Forsch 185:379–382

    Google Scholar 

  5. Cambou B, Klibanov AM (1984a) Biotechnol Bioeng 26:1449–1454

    Google Scholar 

  6. Langrand G, Barrati J, Buono G, Triantaphylides C (1986) Tetrahedron Lett 27:29–32

    Google Scholar 

  7. Cambou B, Klibanov AM (1984b) J Am Chem Soc 106:2687–2692

    Google Scholar 

  8. Kirchner G, Scollar MP, Klibanov AM (1985) J Am Chem Soc 107:7072–7076

    Google Scholar 

  9. Stokes TM, Oehlschlager AC (1987) Tetrahedron Lett 28:2091–2094

    Google Scholar 

  10. Okumura S, Iwai M, Tsujisaka Y (1979) Biochim Biophys Acta 575:156–165

    Google Scholar 

  11. Omar IC, Nishio N, Nagai S (1987) Agric Biol Chem 51:2153–2159

    Google Scholar 

  12. Gerlach D, Missel C, Schreier P (1988) Z Lebensm Unters Forsch 186:315–318

    Google Scholar 

  13. Gerlach D, Schneider S, Göllner T, Kim KS, Schreier P (1988) Screening of lipases for enantiomer resolution of secondary alcohols by esterification in organic medium. In: Schreier P (ed) Bioflavour '87. De Gruyter, Berlin, pp 543–554

    Google Scholar 

  14. Engel K-H (1988) Investigation of chiral compounds in biological systems by chromatographic micromethods. In: Schreier P (ed) Bioflavour '87. de Gruyter, Berlin, pp 75–88

    Google Scholar 

  15. Zaks A, Klibanov AM (1985) Proc Natl Acad Sci USA 82:3192–3196

    Google Scholar 

  16. Engel K-H, Bohnen M (1988) Z Lebensm Unters Forsch (in preparation)

  17. Chen C-S, Fujimoto Y, Girdaukas G, Sih CJ (1982) J Am Chem Soc 104:7294–7299

    Google Scholar 

  18. Deleuze H, Langrand G, Millet H, Baratti J, Buone G, Triantaphylides C (1987) Biochim Biophys Acta 911:117–120

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Engel, KH., Bohnen, M. & Tressl, R. Kinetic resolution of heptan-2-ol-enantiomers by lipase-catalysed esteriîication in organic solvent. Z Lebensm Unters Forch 188, 144–147 (1989). https://doi.org/10.1007/BF01042739

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF01042739

Keywords

Navigation