Regioselective synthesis of ethoxylated glycoside esters using β-glucosidase in supersaturated solutions and lipases in organic solvents
✍ Scribed by Anna Millqvist-Fureby; Chunli Gao; Evgeny N. Vulfson
- Publisher
- John Wiley and Sons
- Year
- 1998
- Tongue
- English
- Weight
- 114 KB
- Volume
- 59
- Category
- Article
- ISSN
- 0006-3592
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✦ Synopsis
Three ethoxylated glycosides, tetraethylene glycol -D-glucoside, tetraethylene glycol -D-xyloside, and methoxy triethyleneglycol -D-glucoside, were prepared via almond -glucoside-catalyzed (trans)glycosylation carried out in supersaturated solutions of glucose or p-nitrophenyl -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, -O-oleoyl tetraethylene glycol -D-glucoside. Novozyme was used for the preparative synthesis of two other monoesters, 6-O-oleoyl (methoxy triethyleneglycol) -D-glucoside and -Ooleoyl tetraethylene glycol -D-xyloside. Two diesters, di-oleoyl tetraethylene glycol -D-glucoside and tetraethylene-bis(6-0-oleoyl glucoside) were also synthesized in good yields using this lipase.