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Efficient synthesis of a long carbohydrate chain alkyl glycoside catalysed by cyclodextrin glycosyltransferase (CGTase).

Svensson, David LU ; Ulvenlund, Stefan and Adlercreutz, Patrick LU (2009) In Biotechnology and Bioengineering 104(5). p.854-861
Abstract
Alkyl glycosides with long carbohydrate groups are surfactants with attractive properties but they are very difficult to synthesize. Here, a method for extension of the carbohydrate group of commercially available dodecyl-beta-D-maltoside (DDM) is presented. (DDM) was converted to dodecyl-beta-D-maltooctaoside (DDMO) in a single step by using a CGTase as catalyst and alpha-cyclodextrin (alpha-CD) as glycosyl donor. The coupling reaction is under kinetic control and the maximum yield depends on the selectivity of the enzyme. The B. macerans CGTase favoured the coupling reaction while the Thermoanaerobacter enzyme also catalysed disproportionation reactions leading to a broader product range. A high ratio alpha-CD/DDM favoured a high yield... (More)
Alkyl glycosides with long carbohydrate groups are surfactants with attractive properties but they are very difficult to synthesize. Here, a method for extension of the carbohydrate group of commercially available dodecyl-beta-D-maltoside (DDM) is presented. (DDM) was converted to dodecyl-beta-D-maltooctaoside (DDMO) in a single step by using a CGTase as catalyst and alpha-cyclodextrin (alpha-CD) as glycosyl donor. The coupling reaction is under kinetic control and the maximum yield depends on the selectivity of the enzyme. The B. macerans CGTase favoured the coupling reaction while the Thermoanaerobacter enzyme also catalysed disproportionation reactions leading to a broader product range. A high ratio alpha-CD/DDM favoured a high yield of DDMO and yields up to 80 % were obtained using the B. macerans enzyme as catalyst. (c) 2009 Wiley Periodicals, Inc. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
alkyl glycoside, cyclodextrin glycosyltransferase, dodecyl, alpha-D-maltooctaoside, cyclodextrin, transglycosylation, coupling, reaction
in
Biotechnology and Bioengineering
volume
104
issue
5
pages
854 - 861
publisher
John Wiley & Sons
external identifiers
  • wos:000271728400003
  • pmid:19609955
  • scopus:70350534537
ISSN
1097-0290
DOI
10.1002/bit.22472
language
English
LU publication?
yes
id
b115c4d9-141d-4caa-ab41-ad83e153aedd (old id 1453007)
date added to LUP
2009-09-01 10:01:03
date last changed
2017-07-02 03:40:07
@article{b115c4d9-141d-4caa-ab41-ad83e153aedd,
  abstract     = {Alkyl glycosides with long carbohydrate groups are surfactants with attractive properties but they are very difficult to synthesize. Here, a method for extension of the carbohydrate group of commercially available dodecyl-beta-D-maltoside (DDM) is presented. (DDM) was converted to dodecyl-beta-D-maltooctaoside (DDMO) in a single step by using a CGTase as catalyst and alpha-cyclodextrin (alpha-CD) as glycosyl donor. The coupling reaction is under kinetic control and the maximum yield depends on the selectivity of the enzyme. The B. macerans CGTase favoured the coupling reaction while the Thermoanaerobacter enzyme also catalysed disproportionation reactions leading to a broader product range. A high ratio alpha-CD/DDM favoured a high yield of DDMO and yields up to 80 % were obtained using the B. macerans enzyme as catalyst. (c) 2009 Wiley Periodicals, Inc.},
  author       = {Svensson, David and Ulvenlund, Stefan and Adlercreutz, Patrick},
  issn         = {1097-0290},
  keyword      = {alkyl glycoside,cyclodextrin glycosyltransferase,dodecyl,alpha-D-maltooctaoside,cyclodextrin,transglycosylation,coupling,reaction},
  language     = {eng},
  number       = {5},
  pages        = {854--861},
  publisher    = {John Wiley & Sons},
  series       = {Biotechnology and Bioengineering},
  title        = {Efficient synthesis of a long carbohydrate chain alkyl glycoside catalysed by cyclodextrin glycosyltransferase (CGTase).},
  url          = {http://dx.doi.org/10.1002/bit.22472},
  volume       = {104},
  year         = {2009},
}