Lipase-catalyzed regioselective acylation of sucrose in two-solvent mixtures

Biotechnology and Bioengineering

Volumn 65, Issue 1, 1999, Pages 10-16

  Ferrer, Manuel ^a   Cruces, M Angeles ^a   Bernabé, Manuel ^b   Ballesteros, Antonio ^a   Plou, Francisco J ^a  

^a CSIC   (Spain)

^b INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

Biotransformations; Lipases; Regioselectivity; Sucrose; Sucrose esters

Indexed keywords

BIOCONVERSION; BIOSYNTHESIS; CATALYSIS; CATALYST SELECTIVITY; ENZYME KINETICS; ESTERIFICATION; MICROORGANISMS; MIXTURES; SOLVENTS; SUGAR (SUCROSE);

BIOTRANSFORMATION; DIMETHYL SULFOXIDE; HUMICOLA LANUGINOSA; REGIOSELECTIVITY; VINYL LAURATE;

ACYLATION;

2 BUTANOL; DIMETHYL SULFOXIDE; SUCROSE; SUCROSE ESTER DERIVATIVE; TRIACYLGLYCEROL LIPASE;

ACYLATION; ARTICLE; BIOTRANSFORMATION; CARBOHYDRATE SYNTHESIS; CATALYSIS; ESTERIFICATION; STEREOCHEMISTRY;

ACYLATION; BINDING SITES; BIOTECHNOLOGY; BUTANOLS; DIMETHYL SULFOXIDE; LIPASE; MAGNETIC RESONANCE SPECTROSCOPY; MITOSPORIC FUNGI; PENTANOLS; SOLVENTS; SUCROSE;

HUMICOLA; THERMOMYCES LANUGINOSUS;

EID: 0033527426     PISSN: 00063592     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1097-0290(19991005)65:1<10::AID-BIT2>3.0.CO;2-L     Document Type: Article

References (38)

1. Carrea G, Riva S, Secundo F, Danieli B. 1989. Enzymatic synthesis of various 1'-O-sucrose and 1'-O-fructose esters. J Chem Soc, Perkin Trans 1, 1057-1061.
2. Chan AW, Ganem B. 1993. A regioselective, chemoenzymatic synthesis of sucrose-1'-methacrylate. Biocatalysis 8:163-169.
3. Chauvin C, Baczko K, Plusquellec D. 1993. New highly regioselective reactions of unprotected sucrose. Synthesis of 2-O-acylsucroses and 2-O-(N-alkylcarbamoyl)sucroses. J Org Chem 58:2291-2295.
4. Chortyk OT, Pomonis JG, Johnson AW. 1996. Synthesis and characterization of insecticidal sucrose esters. J Agric Food Chem 44: 1551-1557.
5. Chowdhary MS, Hough L, Richardson AC. 1984. Sucrochemistry. Part 33. The selective pivaloylation of sucrose. J Chem Soc, Perkin Trans 1, 419-427.
6. Cruces MA, Otero C, Bernabe M, Martin-Lomas M, Ballesteros A. 1992. Enzymatic preparation of acylated sucroses. Ann NY Acad Sci 672: 436-443.
7. Haines AH. 1976. Relative reactivities of hydroxyl groups in carbohydrates. Adv Carbohydr Chem Biochem 33:11-109.
8. Haines AH. 1981. Selective removal of protecting groups in carbohydrate chemistry. Adv Carbohydr Chem Biochem 39:13-70.
9. Ikeda I, Klibanov AM. 1993. Lipase-catalyzed acylation of sugars solubilized in hydrophobic solvents by complexation. Biotechnol Bioeng 42:788-791.
10. Jones JD, Hacking AJ, Cheetham PSJ. 1992. Biological method for protection of 6-position of sucrose and its use in synthesis of disaccharide high-intensity sweetener. Biotechnol Bioeng 39:203-210.
11. Kato A, Arima K. 1971. Inhibitory effect of sucrose ester of lauric acid on the growth of Escherichia coli. Biochem Biophys Res Commun 42: 596-601.
12. Khaled N, Montet D, Farines M, Pina M, Graille J. 1992. Synthesis of sugar mono-esters by biocatalysis. Oléagineux 47:181-190.
13. Khan R. 1984. Chemistry and new uses of sucrose: How important? Pure Appl Chem 56:833-844.
14. Kim JE, Han JJ, Yoon JH, Rhee JS. 1998. Effect of salt hydrate pair on lipase-catalyzed regioselective monoacylation of sucrose. Biotechnol Bioeng 57:121-125.
15. Kononenko OK, Herstein KM. 1956. Nonaqueous solvents for sucrose. Chem Eng Data Ser 1:87-93.
16. Ku MA, Hang YD. 1995. Enzymatic synthesis of esters in organic medium with lipase from Byssochlamys fulva. Biotechnol Lett 17:1081-1084.
17. Laitinen HA, Harris WE. 1975. Chemical analysis. 2nd ed. New York: McGraw-Hill.
18. Liav A, Goren MB. 1986. An improved synthesis of 6-O-mycoloyl-and 6-O-corynomycoloyl-α-α-trehalose with observations on the permethylation analysis of trehalose glycolipids. Carbohydr Res 155:229-235.
19. Nicotra F, Riva S, Secundo F, Zucchelli L. 1989. An interesting example of complementary regioselective acylation of secondary hydroxyl groups by different lipases. Tetrahedron Lett 30:1703-1704.
20. Nishikawa Y, Okabe M, Yoshimoto K, Kurono G, Fukuoka F. 1976. Chemical and biochemical studies on carbohydrate esters. II. Antitumor activity of saturated fatty acids and their ester derivatives against Ehrlich ascites carcinome. Chem Pharm Bull 24:387-393.
21. Paik YH, Swift G. 1995. Polysaccharides as raw materials for the detergent industry. Chem Ind 55-59.
22. Patil DR, Rethwisch DG, Dordick JS. 1991. Enzymatic synthesis of a sucrose-containing polyester in nearly anhydrous organic media. Biotechnol Bioeng 37:639-646.
23. Plou FJ, Cruces MA, Bernabe M, Martin-Lomas M, Parra JL, Ballesteros A. 1995. Enzymatic synthesis of partially acylated sucroses. Annals NY Acad Sci 750:332-337.
24. Plou FJ, Pastor E, Cruces MA, Ferrer M, Ballesteros A. 1998a. Spanish Patent 9802086.
25. Plou FJ, Ferrer M, Nuero OM, Calvo MV, Alcalde M, Reyes F, Ballesteros A. 1998b. Analysis of Tween 80 as an esterase/lipase substrate for lipolytic activity assay. Biotechnol Tech 12:183-186.
26. Polat T, Bazin HG, Linhardt RJ. 1997. Enzyme catalyzed regioselective synthesis of sucrose fatty acid surfactants. J Carbohydr Chem 16: 1319-1325.
27. Reyes F, Byrde RJW. 1973. Partial purification and properties of a β-acetylglucosaminidase from the fungus Sclerotinia fructigena. Biochem J 131:381-388.
28. Rich JO, Bedell BA, Dordick JS. 1995. Controlling enzyme-catalyzed regioselectivity in sugar ester synthesis. Biotechnol Bioeng 45: 426-434.
29. Riva S, Chopineau J, Kieboom APG, Klibanov AM. 1988. Protease-catalyzed regioselective esterification of sugars and related compounds in anhydrous dimethylformamide. J Am Chem Soc 110:584-588.
30. Rubio E, Fernandez-Mayoralas A, Klibanov AM. 1991. Effect of the solvent on enzyme regioselectivity. J Am Chem Soc 113:695-696.
31. Sarney DB, Kapeller H, Fregapane G, Vulfson EN. 1994. Chemoenzymatic synthesis of dissaccharide fatty-acid esters. J Am Oil Chem Soc 71:711-714.
32. Soedjak HS, Spradlin JE. 1994. Enzymatic transesterification of sugars in anhydrous pyridine. Biocatalysis 11:241-248.
33. Vermeire A, Demuynck C, Vandenbossche G, Eechaute W, Geerts ML, Remon JP. 1996. Sucrose laurate gels as a percutaneous delivery system for oestradiol in rabbits. J Pharm Pharmacol 48:463-467.
34. Vlahov IR, Vlahova PI, Linhardt RJ. 1997. Regioselective synthesis of sucrose monoesters as surfactants. J Carbohydr Chem 16:1-10.
35. Wang YF, Lalonde JJ, Momongan M, Bergbreiter DE, Wong CH. 1988. Lipase catalyzed irreversible transesterifications using enol esters as acylating reagents: preparative enantio-and regioselective syntheses of alcohols, glycerol derivatives, sugars, and organometallics. J Am Chem Soc 110:7200-7205.
36. Ward OP, Fang J, Li Z, 1997 Lipase-catalyzed synthesis of a sugar ester containing arachidonic acid. Enzyme Microb Technol 20:52-56.
37. Weber HK, Stecher H, Faber K. 1995. Sensitivity of microbial lipases to acetaldehyde formed by acyl-transfer reactions from vinyl esters. Biotechnol Lett 17:803-808.
38. Woudenberg M, Van Rantwijk F, Sheldon RA. 1996. Regioselective acylation of disaccharides in tert-butyl alcohol catalyzed by C. antarctica lipase. Biotechnol Bioeng 49:328-333.