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Biocatalysis Volume 9, 1994 - Issue 1-4
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Original Article

Selective Lipase-Catalyzed Esterification of Alkyl Glycosides

A.T.J.W. De Goede Laboratory of Organic Chemistry and Catalysis, Delft University of Technology, Julianalaan 136, 2628, BL Delft, The Netherlands
,
M. Van Oosterom Laboratory of Organic Chemistry and Catalysis, Delft University of Technology, Julianalaan 136, 2628, BL Delft, The Netherlands
,
M.P.J. Van Deurzen Laboratory of Organic Chemistry and Catalysis, Delft University of Technology, Julianalaan 136, 2628, BL Delft, The Netherlands
,
R. A. Sheldon Laboratory of Organic Chemistry and Catalysis, Delft University of Technology, Julianalaan 136, 2628, BL Delft, The Netherlands
,
H. Van Bekkum Laboratory of Organic Chemistry and Catalysis, Delft University of Technology, Julianalaan 136, 2628, BL Delft, The Netherlands
&
F. Van Rantwijk Laboratory of Organic Chemistry and Catalysis, Delft University of Technology, Julianalaan 136, 2628, BL Delft, The Netherlands
Pages 145-155 | Published online: 11 Jul 2009

References

  • Brady L., Brzozowski A. M., Derewenda Z. S., Dodson E., Tolley S., Turkenburg J. P. A serine protease triad forms the catalytic centre of a triacylglycerol lipase. Nature 1990; 343: 767–770
  • Brzozowski A. M., Derewenda U., Derewenda Z. S., Dodson G. C. A model for interfacial activation in lipases from the structure of a fungal lipase-inhibitor complex. Nature 1991; 351: 491–494
  • Ciuffreda P., Ronchetti F., Toma L. Acylation of 6-deoxy-L-hexoses: regioselectivity in the enzymatic Iransesterification as compared to chemical esterification. J. Carbohydr. Chem. 1990a; 9: 125–129
  • P Ciuffreda, Colombo D., Ronchetti F., Toma L. Regioselective acylation of 6-deoxy L- and D-hexosides through lipase-catalyzed transesterification. Enhanced reactivity of the 4-OH function in the L series. J Org. Chem. 1990b; 55: 4187–4190
  • Colombo D., Ronchetti F., Toma L. Enzymic acylation of sugars. Rationale of the regioselective butyrylation of secondary hydrolxy groups of D- and L-galacto and monnopyranosides. Tetrahedron 1991; 47: 103–110
  • Colombo D., Ronchetti F., Scala A., Toma L. Enzymic acylation of methyl D- and L-glucopyranosides and 6-dcoxy-glucopyranosides. J. Carbohydr. Chem. 1992; 11: 89–94
  • Derewenda Z. S., Derenda U., Dodson G. The crystal and molecular structure of the Rhiizomucor miehei triacylglyceride lipase at 1.9 Å resolution. J. Mol. BioL 1992; 227: 818–839
  • De Goede A. T.J.W., Beckhuijsen W., Van Rantwijk F., Maat L., Van Bekkum H. Selective lipase-catalyzed 6-O-acylation of alkyl α-D-glucopyranosides using functionalized ethyl esters. Recl. Trav. Chim. Pays-Bas 1993, in the press
  • De Nijs M. P., Maat L., Kieboom A. P.G. Two-step chemo-enzymatic synthesis of octyl 6-O-acyl-α-D-glucopyranoside surfactants from glucose. Reel. Trav. Chim. Pays-Bas 1990; 109: 429–433
  • Dewar M. J.S. New ideas about enzymes. Enzyme 1986; 36: 8
  • Dewar M. J.S., Dieter K. M. Mechanism of the chain extension step in the biosynthesis of fatty acids. Biochemistry 1988; 27: 3302
  • Drueckhammer D. G., Hennen W. J., Pederson R. L., Barbas C. F., Gautheron CM., Krach T., Wong C. H. Enzyme catalysis in synthetic carbohydrate chemistry. Synthesis 1991; 499
  • Gotor V., Pulido R. An improved procedure for regioselective acylation of carbohydrates: novel enzymatic acylation of α-D-glucopyranose and methyl α-D-glucopyranoside. J. Chem. Soc. Perkin Trans. 1991; 491
  • Hennen W. J., Sweers H. M., Wang Y.-F., Wong C.-H. Enzymes in carbohydrate synthesis: lipase-catalyzed selective acylation and deacylation of furanose and pyranose derivatives. J. Org. Chem. 1988; 53: 4939–4945
  • Hölderich W. F., Van Bekkum H. Zeolites in organic synthesis. Stud. Surf. Sci. Catal 1991; 58: 631–726(642)
  • Ishii M. Purification of a thermostable, non-specific lipase from Candida and its use in transesterification. PCT Int. Appl. WO 8802,775. Chem. Abstr. 1988; 110: 20529t, (1989)
  • Kirk O., Björkling F., Godtfredsen S. E. Esters of glycosides and their enzymic manufacture for use as detergents. PCT Int. Appl. WO 89/01480. Chem. Abstr. 1989; 114: 183876e, 1991
  • Mufti K. S., Khan R. A. GB Appl. 1980; 80: 22320, [Chem. Abstr, 96 (1982) 163112j]
  • Pedersen S., Eigtved P. Lipase immobilization and use thereof for ester synthesis. PCT Int. Appl. WO 90/15868. Chem. Abstr. 1990; 114: 224537r, 1991
  • Riva S., Chopinau J., Kieboom A. P.G., Klibanov A. M. Protease-catalyzed regioselective esterification of sugars and related compounds in anhydrous dimethylformamide. J. Am. Chem. Soc 1988; 110: 584–589
  • Straathof A. J.J., Van Bekkum H., Kieboom A. P.G. Efficient preparation of octyl α-D-glucopyranoside monohydrale: a recirculation procedure involving water removal by product crystallization. Starch 1988; 40: 229
  • Therisod M., Klibanov A. M. Facile enzymatic preparation of monoacylated sugars in pyridine. J. Am. Chem. Soc 1986; 108: 5638–5640
  • Therisod M., Klibanov A. M. Regioselective acylation of secondary hydroxyl groups in sugars catalyzed by lipases in organic solvents. J. Am. Chem. Soc 1987; 109: 3977–3981
  • Wang Y.-F., Lalonde J. J., Momongan M., Bergbreiler D. E., Wong C.-H. Lipase catalyzed irreversible transesterifications using enol esters a acylating reagents: preparative enantio- and regioselective syntheses of alcohols, glycerol derivatives, sugars, and organometallics. J. Am. Chem. Soc 1988; 110: 7200–7205

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