Abstract
Enzymatic synthesis of l-alanyl, l-leucyl and l-phenylalanyl esters of d-glucose was carried out in a non-polar solvent using lipases from Rhizomucor miehei and porcine pancreas. The unprotected amino acids at millimolar concentrations were used in presence of 10 to 50% (w/w) glucose of the lipases to give ester yields up to >99%. The reaction mixture on analysis by 2-D NMR showed that the product is a mixture of 6-O-, 3-O- and 2-O-monoesters and 2,6-di-O- and 3,6- di-O-esters.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Boyer V, Stanchev M, Fairbanks AJ, Davis BG (2001) Ready protease catalyzed synthesis of carbohydrate-amino acid conjugates. Chem. Commun. 19: 1908-1909.
Divakar S, Kiran KR, Harikrishna S, Karanth NG (1999) An improved process for the preparation of esters of organic acids and alcohols. Indian Patent 1243/DEL/1999.
Kiran KR, Hari Krishna S, Sureshbabu CV, Karanth NG, Divakar S (2000) An esterification method for determination of lipase activity. Biotechnol. Lett. 22: 1511-1514.
Kiran KR, Manohar B, Divakar S (2001) A central composite rotatabledesign analysis of lipase catalysed synthesis of lauroyl lactic acid at bench-scale level. Enzyme Microb. Technol. 28: 122-128.
Kirk O, Bjorkling F, Godfredsen SE, Larson TS (1992) Fatty acid specificity in lipase catalysed synthesis of glucoside esters. Biocatalyst 6: 127-134.
Lohith K, Vijayakumar GR, Manohar B, Divakar S (2003) An improved enzymatic process for the preparation of amino acyl esters of monosaccharides. Indian Patent NF-492/2003.
Margolin AL (1993) Enzymes in the synthesis of chiral drugs. Enzyme Microb. Technol. 15: 266-280.
Maruyama T, Nagasawa S, Goto M (2002) Enzymatic synthesis of sugar amino acid esters in organic solvents. J. Biosci. Bioeng. 94: 357-361.
Park OJ, Jeon GJ, Yong JW (1999) Protease catalyzed synthesis of disaccharide amino acid esters in organic synthesis. Enzyme Microbial. Tech. 25: 455-462.
Riva S, Chopineau J, Kieboom APJ, Klibanov AM (1988) Protease catalysed regioselective esterification of sugars and related compounds in anhydrous dimethylformamide. J. Am. Chem. Soc. 110: 584-589.
Suzuki Y, Shimizu T, Takeda H, Kanda K (1991) Fermentative or enzymatic manufacture of sugar amino acid esters. Jpn Kokai Tokkyo Koho Japanese Patent JP 03216194 A2 (CA 116:127007b).
Therisod M, Klibanov AM (1986) Enzymatic preparation of monoacylated sugars in pyridine. J. Am. Chem. Soc. 108: 5638-5640.
Zaks A, Dodds DR (1997) Applications of biocatalyst and and bio-transformations to the synthesis of pharmaceuticals. Drug Dev. Today 2: 513-531.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Vijayakumar, G.R., Lohith, K., Somashekar, B.R. et al. Lipase catalyzed synthesis of l-alanyl, l-leucyl and l-phenylalanyl esters of d-glucose using unprotected amino acids. Biotechnology Letters 26, 1323–1328 (2004). https://doi.org/10.1023/B:BILE.0000045627.60538.4f
Issue Date:
DOI: https://doi.org/10.1023/B:BILE.0000045627.60538.4f