Regioselective acylation of disaccharides in tert-butyl alcohol catalyzed by Candida antarctica lipase

Biotechnology and Bioengineering

Volumn 49, Issue 3, 1996, Pages 328-333

  Woudenberg Van Oosterom, Marjolein ^a   Van Rantwijk, Fred ^a   Sheldon, Roger A ^a  

^a DELFT UNIVERSITY OF TECHNOLOGY   (Netherlands)

Author keywords

disaccharides; fatty acid ester; lipase; organic solvent; regioselectivity; transesterification

Indexed keywords

ACYLATION; ALCOHOLS; CATALYSIS; ENZYMES; ESTERS; FUNGI; SOLUBILITY; THERMAL EFFECTS;

CANDIDA ANTARCTICA; DISACCHARIDES; ETHYL BUTANOATE; ETHYL DODECANOATE; LACTOSE; LIPASE; PROTEASES; TREHALOSE;

SUGARS;

DISACCHARIDE; TERT BUTYL ALCOHOL; TRIACYLGLYCEROL LIPASE;

ACYLATION; ARTICLE; CANDIDA; CARBOHYDRATE METABOLISM; CATALYSIS; CELL SPECIFICITY; ENZYME ACTIVITY; ESTERIFICATION; HYDROLYSIS; NONHUMAN; REACTION TIME; SOLUBILITY;

CANDIDA ANTARCTICA; FUNGI;

EID: 0030569896     PISSN: 00063592     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1097-0290(19960205)49:3<328::AID-BIT11>3.0.CO;2-A     Document Type: Article

References (14)

1. Adams, W. F., Schuster, G. 1985. pp. 151-152, 233-235, 406-407. In: G. Schuster (ed.), Emulgatoren für Lebensmittel. Springer-Verlag, Berlin, Heidelberg.
2. Björkling, F., Godtfredsen, S. E., Kirk, O. 1990. Lipase-mediated formation of peroxycarboxylic acids used in catalytic epoxidation of alkenes. J. Chem. Soc. Chem. Commun., 1301-1303.
3. Bjórkling, F., Frykman, H., Godtfredsen, S. E., Kirk, O. 1992. Lipase catalyzed synthesis of peroxycarboxylic acids and lipase mediated oxidations. Tetrahedron 22: 4587-4592.
4. Bock, K., Pedersen, C., Pedersen, H. 1984. Carbon-13 nuclear magnetic resonance data for oligosaccharides. Adv. Carbohydr. Chem. Biochem. 42: 193-225.
5. Carrea, G., Riva, S., Secundo, F. 1989. Enzymatic synthesis of various 1′-O-sucrose and 1-O-fructose esters. J. Chem. Soc. Perkin Trans. I. 1057-1061.
6. de Goede, A. T. J. W., Benckhuijsen, W., van Rantwijk, F., Maat, L., van Bekkum, H. 1993. Selective lipase-catalyzed 6-O-acylation of alkyl α-D-glucopyranosides using functionalized ethyl esters. Recl. Trav. Chim. Pays-Bas 112: 567-572.
7. Guillemard, E., Geniteau-Legendre, M., Mabboux, B., Poilane, I., Kergot, R., Lemaire, G., Petit, J. F., Labarre, C., Quero, A. M. 1993. Antiviral action of trehalose dimycolate against EMC virus: role of macrophages and interferon alpha/bata. Antiviral Res. 22: 201-213.
8. Klibanov, A. M. 1986. Enzymes that work in organic solvents. CHEMTECH 16: 354-359.
9. Kohya, H., Ishii, F., Takano, S., Ebina, T., Ishida, N. 1986. Antitumor effect of a synthetic cord factor, 6,6′-di-O-decanoyl-α,α-trehalose (SS554), in mice. Jpn. J. Cancer Res. 77: 602-609.
10. Riva, S., Chopineau, J., Kicboom, A. P. G., Klibanov, A. M. 1988. Protease-catalyzed regioselective esterification of sugars and related compounds in anhyrous dimethylformamide. J. Am. Chem. Soc. 110: 584-589.
11. Seino, H., Uchibori, T., Nishitani, T., Inamasu, S. 1984. Enzymatic synthesis of carbohydrate esters of fatty acid (I) esterification of sucrose, glucose, fructose and sorbitol. J. Am. Oil Chem. Soc. 61: 1761-1765.
12. 13C-Nuclear magnetic resonance (NMR) spectra of O-acylglucoses. Additivity of shift parameters and its application to structure elucidations. Chem. Pharm. Bull. 28: 2065-2076.
13. Zoete, M. C de, Kock-van Dalen, A. C. Rantwijk, F. van, Sheldon, R. A. 1993 Ester ammoniolysis: A new enzymatic reaction. J Chem. Soc. Chem. Commun., 1831-1832.
14. Zoete, M C. de, Kock-van Dalen, A. C., Rantwijk, F. van, Sheldon, R. A. 1994. A new enzymatic reaction: Enzyme catalyzed ammonolysis of carboxylic esters. Biocatalysis 10: 307-316.