Hydrophobic Complexation Promotes Enzymatic Surfactant Synthesis from Alkyl Glucoside/Cyclodextrin Mixtures
(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:
https://lup.lub.lu.se/record/4659538
- author
- Börner, Tim
LU
; Roger, Kevin
LU
and Adlercreutz, Patrick
LU
- organization
- publishing date
- 2014
- 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 (ACS)
- 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
- 2016-04-01 14:18:45
- date last changed
- 2022-03-29 20:18:35
@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}}, keywords = {{alkylglycoside; glucanotransferase; cyclodextrin; inclusion complex; self-assembly}}, language = {{eng}}, number = {{8}}, pages = {{2623--2634}}, publisher = {{The American Chemical Society (ACS)}}, series = {{ACS Catalysis}}, title = {{Hydrophobic Complexation Promotes Enzymatic Surfactant Synthesis from Alkyl Glucoside/Cyclodextrin Mixtures}}, url = {{http://dx.doi.org/10.1021/cs500192q}}, doi = {{10.1021/cs500192q}}, volume = {{4}}, year = {{2014}}, }