ISSN:
0006-3592
Keywords:
enzymes
;
glycosidases
;
lipases
;
supersaturated solutions
;
organic solvents
;
esterification
;
glycosides
;
ethyleneglycol
;
sugar fatty acid esters
;
surfactants
;
Chemistry
;
Biochemistry and Biotechnology
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Biology
,
Process Engineering, Biotechnology, Nutrition Technology
Notes:
Three ethoxylated glycosides, tetraethylene glycol β-D-glucoside, tetraethylene glycol β-D-xyloside, and methoxy triethyleneglycol β-D-glucoside, were prepared via almond β-glucoside-catalyzed (trans)glycosylation carried out in supersaturated solutions of glucose or p-nitrophenyl β-D-xyloside and the respective polyethylene glycols. The products were isolated and further modified by enzymatic esterification with Candida antarctica and Mucor miehei lipases. The latter enzyme showed a much greater selectivity for the primary hydroxyl group on the polyethylene glycol chain of the glucoside substrate, thus enabling us to obtain exclusively the corresponding monoester, ω-O-oleoyl tetraethylene glycol β-D-glucoside. Novozyme was used for the preparative synthesis of two other monoesters, 6-O-oleoyl (methoxy triethyleneglycol) β-D-glucoside and ω-O-oleoyl tetraethylene glycol β-D-xyloside. Two diesters, di-oleoyl tetraethylene glycol β-D-glucoside and tetraethylene-bis(6-0-oleoyl glucoside) were also synthesized in good yields using this lipase. © 1998 John Wiley & Sons, Inc. Biotechnol Bioeng 59:747-753, 1998.
Additional Material:
4 Ill.
Type of Medium:
Electronic Resource
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