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Regioselective synthesis of ethoxylated glycoside esters using β-glucosidase in supersaturated solutions and lipases in organic solvents

Millqvist-Fureby, Anna LU ; Gao, Chunli and Vulfson, Evgeny N. (1998) In Biotechnology and Bioengineering 59(6). p.747-753
Abstract

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... (More)

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-O-oleoyl glucoside) were also synthesized in good yields using this lipase.

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author
; and
publishing date
type
Contribution to journal
publication status
published
keywords
Enzymes, Esterification, Ethyleneglycol, Glycosidases, Glycosides, Lipases, Organic solvents, Sugar fatty acid esters, Supersaturated solutions, Surfactants
in
Biotechnology and Bioengineering
volume
59
issue
6
pages
7 pages
publisher
John Wiley & Sons Inc.
external identifiers
  • scopus:0032552501
ISSN
0006-3592
DOI
10.1002/(SICI)1097-0290(19980920)59:6<747::AID-BIT11>3.0.CO;2-2
language
English
LU publication?
no
id
430da2b2-09b1-4e80-ad38-33071d68a153
date added to LUP
2025-04-14 17:47:34
date last changed
2025-04-23 11:30:04
@article{430da2b2-09b1-4e80-ad38-33071d68a153,
  abstract     = {{<p>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-O-oleoyl glucoside) were also synthesized in good yields using this lipase.</p>}},
  author       = {{Millqvist-Fureby, Anna and Gao, Chunli and Vulfson, Evgeny N.}},
  issn         = {{0006-3592}},
  keywords     = {{Enzymes; Esterification; Ethyleneglycol; Glycosidases; Glycosides; Lipases; Organic solvents; Sugar fatty acid esters; Supersaturated solutions; Surfactants}},
  language     = {{eng}},
  month        = {{09}},
  number       = {{6}},
  pages        = {{747--753}},
  publisher    = {{John Wiley & Sons Inc.}},
  series       = {{Biotechnology and Bioengineering}},
  title        = {{Regioselective synthesis of ethoxylated glycoside esters using β-glucosidase in supersaturated solutions and lipases in organic solvents}},
  url          = {{http://dx.doi.org/10.1002/(SICI)1097-0290(19980920)59:6<747::AID-BIT11>3.0.CO;2-2}},
  doi          = {{10.1002/(SICI)1097-0290(19980920)59:6<747::AID-BIT11>3.0.CO;2-2}},
  volume       = {{59}},
  year         = {{1998}},
}