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Chemoenzymatic synthesis of β-D-glucosides using cellobiose phosphorylase from Clostridium thermocellum

Karel De Winter, Lisa Van Renterghem UGent, Kathleen Wuyts, Helena Pelantová, Vladimír Křen, Wim Soetaert UGent and Tom Desmet UGent (2015) ADVANCED SYNTHESIS & CATALYSIS. 357(8). p.1961-1969
abstract
Over the past decade, disaccharide phosphorylases have been successfully applied for the synthesis of numerous a-glucosides. In contrast, much less research has been done with respect to the production of beta-glucosides. Although cellobiose phosphorylase was already successfully used for the synthesis of various disaccharides and branched trisaccharides, its glycosylation potential towards small organic compounds has not been explored to date. Unfortunately, disaccharide phosphorylases typically have a very low affinity for non-carbohydrate acceptors, which urges the addition of solvents. The ionic liquid AMMOENG (TM) 101 and ethyl acetate were identified as the most promising solvents, allowing the synthesis of various beta-glucosides. Next to hexyl, heptyl, octyl, nonyl, decyl and undecyl beta-D-glucopyranosides, also the formation of vanillyl 4-O-beta-D-glucopyranoside, 2-phenylethyl beta-D-glucopyranoside, beta-citronellyl beta-D-glucopyranoside and 1-O-beta-D-glucopyranosyl hydroquinone was confirmed by nuclear magnetic resonance spectroscopy and mass spectrometry. Moreover, the stability of cellobiose phosphorylase could be drastically improved by creating cross-linked enzyme aggregates, while the efficiency of the biocatalyst for the synthesis of octyl beta-D-glucopyranoside was doubled by imprinting with octanol. The usefulness of the latter system was illustrated by performing three consecutive batch conversions with octanol imprinted cross-linked enzyme aggregates, yielding roughly 2 g of octyl beta-D-glucopyranoside.
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author
organization
alternative title
Chemoenzymatic synthesis of beta-D-glucosides using cellobiose phosphorylase from Clostridium thermocellum
year
type
journalArticle (original)
publication status
published
subject
keyword
ACCEPTOR SPECIFICITY, ENZYMATIC-SYNTHESIS, ALPHA-ARBUTIN, GLYCOSIDES, STABILITY, BIOTRANSFORMATION, DISACCHARIDE PHOSPHORYLASES, TRANSGLUCOSYLATION, CHAIN ALKYL GLUCOSIDES, SUCROSE PHOSPHORYLASE, stability, glycosylation, beta-glucosides, cross-linked enzyme aggregates, cellobiose phosphorylase
journal title
ADVANCED SYNTHESIS & CATALYSIS
Adv. Synth. Catal.
volume
357
issue
8
pages
1961 - 1969
Web of Science type
Article
Web of Science id
000355235700035
JCR category
CHEMISTRY, APPLIED
JCR impact factor
6.453 (2015)
JCR rank
1/71 (2015)
JCR quartile
1 (2015)
ISSN
1615-4150
DOI
10.1002/adsc.201500077
project
Biotechnology for a sustainable economy (Bio-Economy)
language
English
UGent publication?
yes
classification
A1
copyright statement
I have transferred the copyright for this publication to the publisher
id
6872487
handle
http://hdl.handle.net/1854/LU-6872487
date created
2015-07-10 11:15:09
date last changed
2016-12-19 15:43:30
@article{6872487,
  abstract     = {Over the past decade, disaccharide phosphorylases have been successfully applied for the synthesis of numerous a-glucosides. In contrast, much less research has been done with respect to the production of beta-glucosides. Although cellobiose phosphorylase was already successfully used for the synthesis of various disaccharides and branched trisaccharides, its glycosylation potential towards small organic compounds has not been explored to date. Unfortunately, disaccharide phosphorylases typically have a very low affinity for non-carbohydrate acceptors, which urges the addition of solvents. The ionic liquid AMMOENG (TM) 101 and ethyl acetate were identified as the most promising solvents, allowing the synthesis of various beta-glucosides. Next to hexyl, heptyl, octyl, nonyl, decyl and undecyl beta-D-glucopyranosides, also the formation of vanillyl 4-O-beta-D-glucopyranoside, 2-phenylethyl beta-D-glucopyranoside, beta-citronellyl beta-D-glucopyranoside and 1-O-beta-D-glucopyranosyl hydroquinone was confirmed by nuclear magnetic resonance spectroscopy and mass spectrometry. Moreover, the stability of cellobiose phosphorylase could be drastically improved by creating cross-linked enzyme aggregates, while the efficiency of the biocatalyst for the synthesis of octyl beta-D-glucopyranoside was doubled by imprinting with octanol. The usefulness of the latter system was illustrated by performing three consecutive batch conversions with octanol imprinted cross-linked enzyme aggregates, yielding roughly 2 g of octyl beta-D-glucopyranoside.},
  author       = {De Winter, Karel and Van Renterghem, Lisa and Wuyts, Kathleen and Pelantov{\'a}, Helena and K\v{r}en, Vladim{\'i}r and Soetaert, Wim and Desmet, Tom},
  issn         = {1615-4150},
  journal      = {ADVANCED SYNTHESIS \& CATALYSIS},
  keyword      = {ACCEPTOR SPECIFICITY,ENZYMATIC-SYNTHESIS,ALPHA-ARBUTIN,GLYCOSIDES,STABILITY,BIOTRANSFORMATION,DISACCHARIDE PHOSPHORYLASES,TRANSGLUCOSYLATION,CHAIN ALKYL GLUCOSIDES,SUCROSE PHOSPHORYLASE,stability,glycosylation,beta-glucosides,cross-linked enzyme aggregates,cellobiose phosphorylase},
  language     = {eng},
  number       = {8},
  pages        = {1961--1969},
  title        = {Chemoenzymatic synthesis of \ensuremath{\beta}-D-glucosides using cellobiose phosphorylase from Clostridium thermocellum},
  url          = {http://dx.doi.org/10.1002/adsc.201500077},
  volume       = {357},
  year         = {2015},
}

Chicago
De Winter, Karel, Lisa Van Renterghem, Kathleen Wuyts, Helena Pelantová, Vladimír Křen, Wim Soetaert, and Tom Desmet. 2015. “Chemoenzymatic Synthesis of β-D-glucosides Using Cellobiose Phosphorylase from Clostridium Thermocellum.” Advanced Synthesis & Catalysis 357 (8): 1961–1969.
APA
De Winter, K., Van Renterghem, L., Wuyts, K., Pelantová, H., Křen, V., Soetaert, W., & Desmet, T. (2015). Chemoenzymatic synthesis of β-D-glucosides using cellobiose phosphorylase from Clostridium thermocellum. ADVANCED SYNTHESIS & CATALYSIS, 357(8), 1961–1969.
Vancouver
1.
De Winter K, Van Renterghem L, Wuyts K, Pelantová H, Křen V, Soetaert W, et al. Chemoenzymatic synthesis of β-D-glucosides using cellobiose phosphorylase from Clostridium thermocellum. ADVANCED SYNTHESIS & CATALYSIS. 2015;357(8):1961–9.
MLA
De Winter, Karel, Lisa Van Renterghem, Kathleen Wuyts, et al. “Chemoenzymatic Synthesis of β-D-glucosides Using Cellobiose Phosphorylase from Clostridium Thermocellum.” ADVANCED SYNTHESIS & CATALYSIS 357.8 (2015): 1961–1969. Print.