Advertisement

Enzymatic Esterification of Compounds Possessing Multifunctional Hydroxyl and Carboxyl Groups

  • Soundar Divakar
Chapter

Abstract

This entire chapter is devoted to the esterification reactions involving compounds containing multifunctional groups like OH, COOH, CH3 and CHO. The description involves optimisation of reaction conditions for use of lipases in nonpolar solvents under low water activity by both conventional and response surface methodological conditions. It attempts to bring out the superiority of lipase catalysis over chemical synthesis in the few reactions discussed. Esterification of the OH group of lactic acid with the COOH group of few long-chain fatty acids to synthesise 2-O-alkanoyl acids is discussed in detail. This is followed by the work on the preparation of tolyl esters, protocatechuic aldehyde esters, 4-t-butylcyclohexyl acetate and acetylation of β-cyclodextrin. State of the lipases employed under nonaqueous solvents in the above-mentioned reactions is best brought by studies on thermostability and scanning electron microscopy. The role of water, constituting the micro-aqueous phase around the enzyme during its employment under nonpolar conditions, attempts to explain the integrity of the enzyme under such conditions, in terms of developing a theoretical model on the micro-aqueous pH and various equilibria occurring at and associated with the micro-aqueous phase.

Keywords

Lactic Acid Stearic Acid Esterification Reaction Anthranilic Acid Lactic Acid Concentration 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

References

  1. Atkins PW (1987) Physical chemistry, 2nd edn. Oxford ELBS, Oxford Press, Oxford, p 280Google Scholar
  2. Brown JR, Guther MLS, Field RA, Ferguson MAJ (1997) Hydrophobic mannosides act as acceptors for trypanosome α-mannosyltransferases. Glycobiology 7:549–558PubMedCrossRefGoogle Scholar
  3. Burdock GA (1994) In Fenaroli’s handbook of flavor ingredients, vol II, 3rd edn. CRC Press, Boca RatonGoogle Scholar
  4. Chulalaksanaukul W, Condort JS, Combes D (1992) Kinetics of geranyl acetate synthesis by lipase catalyzed transesterification in n-hexane. Enzyme Microb Technol 14:293–298CrossRefGoogle Scholar
  5. Divakar S (2003) Lipase catalysed regioselective esterification of protocatechuic aldehyde. Indian J Chem Sect B 42B:1119–1122Google Scholar
  6. Food Chemical Codex specificationsGoogle Scholar
  7. Habulin M, Krmelj V (1996) Synthesis of oleic acid esters catalyzed by immobilized lipase. J Agric Food Chem 44(1):338–342CrossRefGoogle Scholar
  8. Hahn-Hagerdal B (1986) Water activity a possible external regulator in biotechnical processes. Enzyme Microb Technol 8:322–327CrossRefGoogle Scholar
  9. Halling PJ (1989) Organic liquids and biocatalysts theory and practice. Trends Biotechnol 7:50–52CrossRefGoogle Scholar
  10. Janssen AEM, Sjursnes BJ, Vakurov AV, Halling PJ (1999) Kinetics of lipase catalyzed esterification in organic media correct model and solvent effects on parameters. Enzyme Microb Technol 24:463–470CrossRefGoogle Scholar
  11. Karger BL, Stern RL, Zannucci JF (1968) Anal Chem 40(4):727CrossRefGoogle Scholar
  12. Kiran KR, Divakar S (2001) Lipase catalysed esterification of organic acids with lactic acid. J Biotechnol 87:109–121PubMedCrossRefGoogle Scholar
  13. Kiran KR, Divakar S (2002) Enzyme inhibition by p-cresol and lactic acid in lipase mediated syntheses of p-cresyl acetate and stearoyl lactic acid A kinetic study. World J Microbiol Biotechnol 18:707–712CrossRefGoogle Scholar
  14. Kiran KR, Karanth NG, Divakar S (1998) An improved enzymatic process for the preparation of fatty acid hydroxyacid ester. Indian Patent, 1978/DEL/98 187313Google Scholar
  15. Kiran KR, Karanth NG, Divakar S (1999) Preparation of steroyl lactic acid catalysed by immobilized lipases from Mucor miehei and porcine pancreas optimization using response surface methodology. Appl Microbiol Technol 52:579–584CrossRefGoogle Scholar
  16. Kiran KR, Manohar B, Karanth NG, Divakar S (2000) Response Surface Methodological study of esterification of lactic acid with palmitic acid catalysed by immobilised lipases from Mucor miehei and porcine pancreas. Z Lebm Unt Fors 211:130–135Google Scholar
  17. Kiran KR, Manohar B, Divakar S (2001a) A central composite rotatable design analysis of lipase catalysed synthesis of lauroyl lactic acid at bench-scale level. Enzyme Microb Technol 29:122–128CrossRefGoogle Scholar
  18. Kiran KR, Suresh-Babu CV, Divakar S (2001b) Thermostability of porcine pancreas lipase in non-aqueous media. Process Biochem 36:885–892CrossRefGoogle Scholar
  19. Kiran KR, Karanth NG, Divakar S (2002) Hydrogen ion concentration at the microaqueous phase in lipase catalysed esterification in non-aqueous organic media – steroyllactic acid. Ind J Biochem Biophys 39:101–105Google Scholar
  20. Lee Y, Howard LR, Villalon B (1995) Flavonoids and antioxidant activity of fresh pepper (C. annum) cultivars. J Food Sci 60:473–476CrossRefGoogle Scholar
  21. Maheswaran MM, Divakar S (1997) Structural studies on inclusion compounds of β-cyclodextrin with some substituted phenols. J Incln Phenomenon 27:113–126CrossRefGoogle Scholar
  22. Manohar B, Divakar S (2002) Application of central composite rotatable design to lipase catalyzed syntheses of m-cresyl acetate. World J Microbiol Biotechnol 18:745–751CrossRefGoogle Scholar
  23. Manohar B, Divakar S (2004) Porcine pancreas lipase acetylation of beta-cyclodextrin anchored 4-t-butylcyclohexanol. Indian J Chem Sect B 43B:2661–2665Google Scholar
  24. Pattekhan HH, Divakar S (2001) Regioselectivity in the preparation of 2-hydroxy-4-ethoxybenzaldehyde from resorcinol in presence of β- cyclodextrin and its derivatives. J Mol Catal A Chem 169(2001):185–191CrossRefGoogle Scholar
  25. Pattekhan HH, Divakar S (2002) Regioselective acetylation of 4-t-butylcyclohexanol in the presence of β-cyclodextrin and its derivatives. J Mol Catal A Chem 184:79–83CrossRefGoogle Scholar
  26. Roquett Catalog (1991) Kleptose-β-Cyclodextrin www.roquette-food.com
  27. Suresh-Babu CV, Divakar S (2001) Selection of alcohols through Plackett-Burman design in lipase catalyzed syntheses of anthranilic acid. J Am Oil Chem Soc 78:49–52CrossRefGoogle Scholar
  28. Suresh-Babu CV, Kiran KR, Divakar S (2001) Scanning electron microscopic studies of lipase catalysed esterification catalysis for the synthesis of stearoyl lactate and p-cresyl laurate. World J Microbiol Biotechnol 17:659–665CrossRefGoogle Scholar
  29. Suresh-Babu CV, Karanth NG, Divakar S (2002) Lipase catalysed esterification of cresols. Ind J Chem Sect B 41B:1068–1071Google Scholar
  30. Valivety RH, Halling PJ, Macrae AR (1992) Rhizomucor miehei lipase remains highly active at water activity below 0.001. FEBS Lett 301:258–260PubMedCrossRefGoogle Scholar
  31. Zaks A, Klibanov AM (1988) Enzyme catalysis in monophasic organic solvents. J Biol Chem 263:3194–3201PubMedGoogle Scholar

Copyright information

© Springer India 2013

Authors and Affiliations

  1. 1.Central Food Technological Research InstituteMysoreIndia

Personalised recommendations