Stabilization of enzyme activity during the esterification of lactic acid in hydrophobic ethers and ketones as reaction media that are miscible with lactic acid despite their high hydrophobicity

Enzyme and Microbial Technology

Volumn 43, Issue 3, 2008, Pages 309-316

  Hasegawa, Satoshi ^a   Azuma, Masanori ^a   Takahashi, Koji ^a  

^a YAMAGATA UNIVERSITY   (Japan)

Author keywords

Acidic and polar reactant; Esterification; Ether; Ketone; Lactic acid; Lipase

Indexed keywords

ADDITION REACTIONS; BIOCHEMICAL ENGINEERING; BODY FLUIDS; CATALYSTS; CHEMICAL MODIFICATION; COMPUTER NETWORKS; ENZYMES; ESTERIFICATION; ESTERS; ETHANOL; ETHERS; FLUIDS; FOOD ADDITIVES; HYDROPHOBICITY; KETONES; LACTIC ACID; ORGANIC ACIDS; ORGANIC COMPOUNDS; ORGANIC SOLVENTS; PROTEINS; REACTION KINETICS; SOLVENTS;

ACID CONCENTRATIONS; ELSEVIER (CO); ENZYMATIC ESTERIFICATION; ENZYME REACTIONS; ETHYL LACTATE; HYDROPHOBIC SOLVENTS; NON-AQUEOUS; POLAR ALCOHOLS; POLAR SOLVENTS; REACTION MEDIUM; REPEATED BATCH; SOLVENT FREE SYSTEMS;

ENZYME ACTIVITY;

ETHER; KETONE; LACTIC ACID;

ARTICLE; CONCENTRATION (PARAMETERS); ENZYME ACTIVITY; ENZYME MECHANISM; ENZYME STABILITY; ESTERIFICATION; HYDROPHOBICITY;

EID: 46449135047     PISSN: 01410229     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.enzmictec.2008.03.017     Document Type: Article

References (21)

1. Datta R., and Henry M. Lactic acid: recent advances in products, processes and technologies-a review. J Chem Technol Biotechnol 81 (2006) 1119-1129
2. Hayes D.G. The catalytic activity of lipases toward hydroxy fatty acids-a review. J Am Oil Chem Soc 73 (1996) 543-549
3. Bousquet M.P., Willemot R.M., Monsan P., and Boures E. Enzymatic synthesis of AHA derivatives for cosmetic application. J Mol Catal B-Enzym 5 (1998) 49-53
4. Sanz M.T., Murga R., Beltran S., Cabezas J.L., and Coca J. Kinetic study for the reactive system of lactic acid esterification with methanol: methyl lactate hydrolysis reaction. Ind Eng Chem Res 43 (2004) 2049-2053
5. Reetz M.T. Lipases as practical biocatalysts. Curr Opin Chem Biol 6 (2002) 145-150
6. Yahya A.R.M., Anderson W.A., and Moo-Young M. Ester synthesis in lipase-catalyzed reactions. Enzyme Microb Technol 23 (1998) 438-450
7. Ohya Y., Sugitou T., and Ouchi T. Polycondensation of α-hydroxy acids by enzymes or PEG-modified enzymes in organic media. J Macromol Sci Pure A32 (1995) 179-190
8. Dordick J.S. Enzymatic catalysis in monophasic organic-solvents. Enzyme Microb Technol 11 (1989) 194-211
9. Pirozzi D., and Greco G. Lipase-catalyzed transformations for the synthesis of butyl lactate: a comparison between esterification and transesterification. Biotechnol Prog 22 (2006) 444-448
10. Roenne T.H., Xu X.B., and Tan T.W. Lipase-catalyzed esterification of lactic acid with straight-chain alcohols. J Am Oil Chem Soc 82 (2005) 881-885
11. Pirozzi D., and Greco G. Activity and stability of lipases in the synthesis of butyl lactate. Enzyme Microb Technol 34 (2004) 94-100
12. Wei D.Z., Gu C.N., Song Q.X., and Su W. Enzymatic esterification for glycoside lactate synthesis in organic solvent. Enzyme Microb Technol 33 (2003) 508-512
13. Torres C., and Otero C. Part III. Direct enzymatic esterification of lactic acid with fatty acids. Enzyme Microb Technol 29 (2001) 3-12
14. Torres C., Otero C., and Part I. Enzymatic synthesis of lactate and glycolate esters of fatty alcohols. Enzyme Microb Technol 25 (1999) 745-752
15. From M., Adlercreutz P., and Mattiasson B. Lipase catalyzed esterification of lactic acid. Biotechnol Lett 19 (1997) 315-317
16. Hasegawa S, Azuma M, Takahashi K. Enzymatic esterification of lactic acid, utilizing the basicity of particular polar organic solvents to suppress the acidity of lactic acid. J Chem Technol Biotechnol, in press, doi:10.1002/jctb.1935.
17. Kamlet M.J., Abboud J.L.M., Abraham M.H., and Taft R.W. Linear solvation energy relationships. 23. A comprehensive collection of the solvatochromic parameters, π*, α, and β, and some methods for simplifying the generalized solvatochromic equation. J Org Chem 48 (1983) 2877-2887
18. Marcus Y. The properties of organic liquids that are relevant to their use as solvating solvents. Chem Soc Rev 22 (1993) 409-416
19. Laane C., Boeren S., Vos K., and Veeger C. Rules for optimization of biocatalysis in organic solvents. Biotechnol Bioeng 30 (1987) 81-87
20. In: David RL (Ed). CRC handbook of chemistry and physics. 80th ed. (1999), CRC Press, Boca Raton 16/42-116/47
21. Castillo E., Dossat V., Marty A., Condoret J.S., and Combes D. The role of silica gel in lipase-catalyzed esterification reactions of high-polar substrates. J Am Oil Chem Soc 74 (1997) 77-85