Advanced

Hydrophobic Complexation Promotes Enzymatic Surfactant Synthesis from Alkyl Glucoside/Cyclodextrin Mixtures

Börner, Tim LU ; Roger, Kevin LU and Adlercreutz, Patrick LU (2014) In ACS Catalysis 4(8). p.2623-2634
Abstract
The unique ability of cyclodextrin glycosyltransferase to form and utilize the cyclic maltooligosaccharide cyclodextrin (CD) makes this enzyme an attractive catalyst for the synthesis of alkyl glycosides. Here, we characterize the sugar headgroup elongation of alkyl glucosides (acceptor) via two transglycosylation reactions from either a linear (maltohexose) or a cyclic (CD) glycosyl donor. Inclusion complex formation overcomes both poor substrate solubility and aggregation. We have used pure alkyl glucosides and alpha CD as model compounds. The complex between CD and alkyl glucoside was efficiently used as a substrate. Kinetic and thermodynamic measurements allow the prediction of the optimal synthesis conditions. This optimum corresponds... (More)
The unique ability of cyclodextrin glycosyltransferase to form and utilize the cyclic maltooligosaccharide cyclodextrin (CD) makes this enzyme an attractive catalyst for the synthesis of alkyl glycosides. Here, we characterize the sugar headgroup elongation of alkyl glucosides (acceptor) via two transglycosylation reactions from either a linear (maltohexose) or a cyclic (CD) glycosyl donor. Inclusion complex formation overcomes both poor substrate solubility and aggregation. We have used pure alkyl glucosides and alpha CD as model compounds. The complex between CD and alkyl glucoside was efficiently used as a substrate. Kinetic and thermodynamic measurements allow the prediction of the optimal synthesis conditions. This optimum corresponds to the transition between a donor-limiting and an acceptor-limiting regime. The resulting rational design should lead to the practical development of a cost-efficient industrial synthesis. Our findings with respect to the importance of complexation should also readily apply to other enzymatic systems. (Less)
Please use this url to cite or link to this publication:
author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
alkylglycoside, glucanotransferase, cyclodextrin, inclusion complex, self-assembly
in
ACS Catalysis
volume
4
issue
8
pages
2623 - 2634
publisher
The American Chemical Society
external identifiers
  • wos:000339983800025
  • scopus:84905456009
ISSN
2155-5435
DOI
10.1021/cs500192q
language
English
LU publication?
yes
id
44f328c6-120b-429a-a61d-e718601fac8e (old id 4659538)
date added to LUP
2014-09-25 09:09:28
date last changed
2017-01-01 06:10:27
@article{44f328c6-120b-429a-a61d-e718601fac8e,
  abstract     = {The unique ability of cyclodextrin glycosyltransferase to form and utilize the cyclic maltooligosaccharide cyclodextrin (CD) makes this enzyme an attractive catalyst for the synthesis of alkyl glycosides. Here, we characterize the sugar headgroup elongation of alkyl glucosides (acceptor) via two transglycosylation reactions from either a linear (maltohexose) or a cyclic (CD) glycosyl donor. Inclusion complex formation overcomes both poor substrate solubility and aggregation. We have used pure alkyl glucosides and alpha CD as model compounds. The complex between CD and alkyl glucoside was efficiently used as a substrate. Kinetic and thermodynamic measurements allow the prediction of the optimal synthesis conditions. This optimum corresponds to the transition between a donor-limiting and an acceptor-limiting regime. The resulting rational design should lead to the practical development of a cost-efficient industrial synthesis. Our findings with respect to the importance of complexation should also readily apply to other enzymatic systems.},
  author       = {Börner, Tim and Roger, Kevin and Adlercreutz, Patrick},
  issn         = {2155-5435},
  keyword      = {alkylglycoside,glucanotransferase,cyclodextrin,inclusion complex,self-assembly},
  language     = {eng},
  number       = {8},
  pages        = {2623--2634},
  publisher    = {The American Chemical Society},
  series       = {ACS Catalysis},
  title        = {Hydrophobic Complexation Promotes Enzymatic Surfactant Synthesis from Alkyl Glucoside/Cyclodextrin Mixtures},
  url          = {http://dx.doi.org/10.1021/cs500192q},
  volume       = {4},
  year         = {2014},
}