Abstract
The acylation of sucrose with vinyl laurate in dimethylsulfoxide was catalyzed by Celite (28% conversion in 24 h at 40 °C, 150 mg catalyst ml−1), Eupergit C (11% conversion in 24 h at 60 °C, 150 mg catalyst/ml), and even the simple Na2HPO4 (17% conversion in 24 h at 40 °C, 20 mg catalyst ml−1). These chemical acylations must therefore be taken into account in acylations of hydroxyl-containing compounds with enol esters in polar solvents using immobilized enzymes.
Similar content being viewed by others
References
Bornscheuer UT, Yamane T (1995) Fatty acid vinyl esters as acylating agents: a new method for the enzymatic synthesis of monoacylglycerols. J. Am. Oil. Chem. Soc. 72: 193–197.
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.
Cruces MA, Otero C, Bernabé M, Martin-Lomas M, Ballesteros A (1992) Enzymatic preparation of acylated sucroses. Ann. N.Y. Acad. Sci. 672: 436–443.
Ferrer M, Cruces MA, Bernabé M, Ballesteros A, Plou FJ (1999) Lipase-catalyzed regioselective acylation of sucrose in twosolvent mixtures. Biotechnol. Bioeng., in press.
Ferro V, Meldal M, Bock K (1994) Synthesis of 2′-and 2′'-O-acylated maltotriosides as potential fluorescence-quenched substrates for α-amylase. J. Chem. Soc. Perkin Trans.: 2169–2176.
Haines AH (1976) Relative reactivities of hydroxyl groups in carbohydrates. Adv. Carbohydr. Chem. Biochem. 33: 11–109.
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.
Kononenko OK, Herstein KM (1956) Nonaqueous solvents for sucrose. Chem. Eng. Data Series 1: 87–93.
Plou FJ, Cruces MA, Bernabé M, Martin-Lomas M, Parra JL, Ballesteros A (1995) Enzymatic synthesis of partially acylated sucroses. Ann. N.Y. Acad. Sci. 750: 332–337.
Plou FJ, Pastor E, Cruces MA, Ferrer M, Ballesteros A (1998) Procedimiento para la obtención selectiva de 2-O-lauroilsacarosa. Spanish Patent 9802086.
Polat T, Bazin HG, Linhardt RJ (1997) Enzyme catalyzed regioselective synthesis of sucrose fatty acid surfactants. J. Carbohydr. Chem. 16: 1319–1325.
Rich JO, Bedell BA, Dordick JS (1995) Controlling enzymecatalyzed regioselectivity in sugar ester synthesis. Biotechnol. Bioeng. 45: 426–434.
Soedjak HS, Spradlin JE (1994) Enzymatic trans-esterification of sugars in anhydrous pyridine. Biocatalysis 11: 241–248.
Sweeley CC, Bentley R, Makita M, Wells WW (1963) Gas-liquid chromatography of trimethylsilyl derivatives of sugars and related substances. J. Am. Chem. Soc. 85: 2497–2507.
Therisod M, Klibanov AM (1986) Facile enzymatic preparation of monoacylated sugars in pyridine. J. Am. Chem. Soc. 108: 5638–5640.
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.
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.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Plou, F., Cruces, M., Pastor, E. et al. Acylation of sucrose with vinyl esters using immobilized hydrolases: demonstration that chemical catalysis may interfere with enzymatic catalysis. Biotechnology Letters 21, 635–639 (1999). https://doi.org/10.1023/A:1005597906555
Issue Date:
DOI: https://doi.org/10.1023/A:1005597906555