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alpha-Amylase-catalysed synthesis of alkyl glycosides

Svensson, Julia LU ; Svensson, David LU and Adlercreutz, Patrick LU (2005) In Journal of Molecular Catalysis B: Enzymatic 37(1-6). p.84-87
Abstract
Alkyl glycosides were synthesised from starch and alcohols using Aspergillus oryzae a-amylase as catalyst. In the degradation of starch by a-amylase, the alcohols competed with water as glycosyl acceptors. In the reaction with methanol, methyl maltoside and methyl maltotrioside were the main alcoholysis products. Conversion of 45 g/1 starch in 30% methanol resulted in a product mixture containing 26 mM maltooligosaccharides and 3.6 mM methyl glycosides. With ethanol, propanol and butanol, alkyl maltosides and alkyl maltotetraosides were detected, and with benzyl alcohol, benzyl glycosides having two, three or five glucose units were formed. No alcoholysis reaction occurred with hexanol or octanol. In conclusion, alpha-amylase is promising... (More)
Alkyl glycosides were synthesised from starch and alcohols using Aspergillus oryzae a-amylase as catalyst. In the degradation of starch by a-amylase, the alcohols competed with water as glycosyl acceptors. In the reaction with methanol, methyl maltoside and methyl maltotrioside were the main alcoholysis products. Conversion of 45 g/1 starch in 30% methanol resulted in a product mixture containing 26 mM maltooligosaccharides and 3.6 mM methyl glycosides. With ethanol, propanol and butanol, alkyl maltosides and alkyl maltotetraosides were detected, and with benzyl alcohol, benzyl glycosides having two, three or five glucose units were formed. No alcoholysis reaction occurred with hexanol or octanol. In conclusion, alpha-amylase is promising for the one-step synthesis of alkyl glycosides having more than one monosaccharide unit, which are difficult to synthesise in other ways. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
biodegradable surfactant, alpha-amylase, alkyl glycoside, biosurfactant, alcoholysis
in
Journal of Molecular Catalysis B: Enzymatic
volume
37
issue
1-6
pages
84 - 87
publisher
Elsevier
external identifiers
  • wos:000234026100013
  • scopus:27944490764
ISSN
1873-3158
DOI
10.1016/j.molcatb.2005.09.009
language
English
LU publication?
yes
id
498e0b6c-61f7-427b-ad5f-a509f57d0429 (old id 210737)
date added to LUP
2007-08-03 12:17:33
date last changed
2017-07-02 03:28:39
@article{498e0b6c-61f7-427b-ad5f-a509f57d0429,
  abstract     = {Alkyl glycosides were synthesised from starch and alcohols using Aspergillus oryzae a-amylase as catalyst. In the degradation of starch by a-amylase, the alcohols competed with water as glycosyl acceptors. In the reaction with methanol, methyl maltoside and methyl maltotrioside were the main alcoholysis products. Conversion of 45 g/1 starch in 30% methanol resulted in a product mixture containing 26 mM maltooligosaccharides and 3.6 mM methyl glycosides. With ethanol, propanol and butanol, alkyl maltosides and alkyl maltotetraosides were detected, and with benzyl alcohol, benzyl glycosides having two, three or five glucose units were formed. No alcoholysis reaction occurred with hexanol or octanol. In conclusion, alpha-amylase is promising for the one-step synthesis of alkyl glycosides having more than one monosaccharide unit, which are difficult to synthesise in other ways.},
  author       = {Svensson, Julia and Svensson, David and Adlercreutz, Patrick},
  issn         = {1873-3158},
  keyword      = {biodegradable surfactant,alpha-amylase,alkyl glycoside,biosurfactant,alcoholysis},
  language     = {eng},
  number       = {1-6},
  pages        = {84--87},
  publisher    = {Elsevier},
  series       = {Journal of Molecular Catalysis B: Enzymatic},
  title        = {alpha-Amylase-catalysed synthesis of alkyl glycosides},
  url          = {http://dx.doi.org/10.1016/j.molcatb.2005.09.009},
  volume       = {37},
  year         = {2005},
}