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Cyclodextrin glucanotransferase (CGTase) catalyzed synthesis of dodecyl glucooligosides by transglycosylation using alpha-cyclodextrin or starch

Mathew, Sindu LU and Adlercreutz, Patrick LU (2012) In Carbohydrate Polymers 87(1). p.574-580
Abstract
Dodecyl glucooligosides, a class of interesting non ionic surfactant molecules were synthesized by cyclodextrin glucanotransferase from Bacillus macerans using either alpha-cyclodextrin (alpha-CD) or soluble starch as glycosyl donor and dodecyl beta-D-glucoside (C(12)G(1)) or dodecyl beta-D-maltoside (C(12)G(2)) as acceptor substrates. The primary coupling products obtained in the respective reactions were identified as dodecyl glucoheptaoside and dodecyl maltooctaoside by mass spectrometry. Higher yields of coupling products were obtained using alpha-CD as donor, while more dispoportionation occurred with starch. Nearly 78% conversion of the acceptor substrate C(12)G(1) into dodecyl glucooligosides could be achieved at 132 mu g/ml of... (More)
Dodecyl glucooligosides, a class of interesting non ionic surfactant molecules were synthesized by cyclodextrin glucanotransferase from Bacillus macerans using either alpha-cyclodextrin (alpha-CD) or soluble starch as glycosyl donor and dodecyl beta-D-glucoside (C(12)G(1)) or dodecyl beta-D-maltoside (C(12)G(2)) as acceptor substrates. The primary coupling products obtained in the respective reactions were identified as dodecyl glucoheptaoside and dodecyl maltooctaoside by mass spectrometry. Higher yields of coupling products were obtained using alpha-CD as donor, while more dispoportionation occurred with starch. Nearly 78% conversion of the acceptor substrate C(12)G(1) into dodecyl glucooligosides could be achieved at 132 mu g/ml of CGTase in 20 min, while 93% of C(12)G(2) could be transformed into products at 17.6 mu g/ml of enzyme in 120 min using soluble starch as donor substrate. For applications requiring pure compounds like C(12)G(7), synthesis using alpha-CD is advantageous. However, for applications in which a mixture of elongated alkyl glycosides is needed, reactions employing starch are clearly competitive. (C) 2011 Elsevier Ltd. All rights reserved. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
Transglycosylation, Alkyl glycosides, Surfactant, Cyclodextrin, glucanotransferase, Disproportionation reactions
in
Carbohydrate Polymers
volume
87
issue
1
pages
574 - 580
publisher
Elsevier
external identifiers
  • wos:000297389000076
  • scopus:80054771637
ISSN
0144-8617
DOI
10.1016/j.carbpol.2011.08.023
language
English
LU publication?
yes
id
846db9be-cde0-4c61-ad98-3a878883f3ac (old id 2278898)
date added to LUP
2012-01-11 13:27:54
date last changed
2017-04-23 03:05:22
@article{846db9be-cde0-4c61-ad98-3a878883f3ac,
  abstract     = {Dodecyl glucooligosides, a class of interesting non ionic surfactant molecules were synthesized by cyclodextrin glucanotransferase from Bacillus macerans using either alpha-cyclodextrin (alpha-CD) or soluble starch as glycosyl donor and dodecyl beta-D-glucoside (C(12)G(1)) or dodecyl beta-D-maltoside (C(12)G(2)) as acceptor substrates. The primary coupling products obtained in the respective reactions were identified as dodecyl glucoheptaoside and dodecyl maltooctaoside by mass spectrometry. Higher yields of coupling products were obtained using alpha-CD as donor, while more dispoportionation occurred with starch. Nearly 78% conversion of the acceptor substrate C(12)G(1) into dodecyl glucooligosides could be achieved at 132 mu g/ml of CGTase in 20 min, while 93% of C(12)G(2) could be transformed into products at 17.6 mu g/ml of enzyme in 120 min using soluble starch as donor substrate. For applications requiring pure compounds like C(12)G(7), synthesis using alpha-CD is advantageous. However, for applications in which a mixture of elongated alkyl glycosides is needed, reactions employing starch are clearly competitive. (C) 2011 Elsevier Ltd. All rights reserved.},
  author       = {Mathew, Sindu and Adlercreutz, Patrick},
  issn         = {0144-8617},
  keyword      = {Transglycosylation,Alkyl glycosides,Surfactant,Cyclodextrin,glucanotransferase,Disproportionation reactions},
  language     = {eng},
  number       = {1},
  pages        = {574--580},
  publisher    = {Elsevier},
  series       = {Carbohydrate Polymers},
  title        = {Cyclodextrin glucanotransferase (CGTase) catalyzed synthesis of dodecyl glucooligosides by transglycosylation using alpha-cyclodextrin or starch},
  url          = {http://dx.doi.org/10.1016/j.carbpol.2011.08.023},
  volume       = {87},
  year         = {2012},
}