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Enzymatic route to alkyl glycosides having oligomeric head groups

Svensson, David LU ; Ulvenlund, Stefan LU and Adlercreutz, Patrick LU (2009) In Green Chemistry 11(8). p.1222-1226
Abstract
Cyclodextrin glycosyl transferase (CGTase) from Bacillus macerans was used to catalyse the coupling of alpha-cyclodextrin to alkyl beta-glycosides. The acceptor substrate dodecyl beta-maltoside was thus converted to dodecyl beta-D-maltooctaoside. Further coupling steps and disproportionation reactions occurred, but by optimisation of the reaction time, a yield of 50% of the primary coupling product was obtained. The method worked well for a range of acceptors with different length of the carbohydrate part (1-3 glucose residues) and the hydrocarbon chain (10-14 carbon atoms). With respect to the principles of green chemistry, the method is superior to previously used methods involving protection/deprotection reactions.
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Green Chemistry
volume
11
issue
8
pages
1222 - 1226
publisher
Royal Society of Chemistry
external identifiers
  • wos:000268747700021
  • scopus:68949210467
ISSN
1463-9270
DOI
10.1039/b904849a
language
English
LU publication?
yes
id
787e3daa-7b75-466e-98c1-796e4ff1cfe8 (old id 1478309)
date added to LUP
2009-09-23 09:06:42
date last changed
2017-04-23 03:27:40
@article{787e3daa-7b75-466e-98c1-796e4ff1cfe8,
  abstract     = {Cyclodextrin glycosyl transferase (CGTase) from Bacillus macerans was used to catalyse the coupling of alpha-cyclodextrin to alkyl beta-glycosides. The acceptor substrate dodecyl beta-maltoside was thus converted to dodecyl beta-D-maltooctaoside. Further coupling steps and disproportionation reactions occurred, but by optimisation of the reaction time, a yield of 50% of the primary coupling product was obtained. The method worked well for a range of acceptors with different length of the carbohydrate part (1-3 glucose residues) and the hydrocarbon chain (10-14 carbon atoms). With respect to the principles of green chemistry, the method is superior to previously used methods involving protection/deprotection reactions.},
  author       = {Svensson, David and Ulvenlund, Stefan and Adlercreutz, Patrick},
  issn         = {1463-9270},
  language     = {eng},
  number       = {8},
  pages        = {1222--1226},
  publisher    = {Royal Society of Chemistry},
  series       = {Green Chemistry},
  title        = {Enzymatic route to alkyl glycosides having oligomeric head groups},
  url          = {http://dx.doi.org/10.1039/b904849a},
  volume       = {11},
  year         = {2009},
}