Ghent University Academic Bibliography

Advanced

Synthesis and evaluation of 2-deoxy-2-amino-β-cellobiosides as cellulase inhibitors

Tom Desmet UGent, Marc Claeyssens, Kathleen Piens UGent and Wim Nerinckx UGent (2010) JOURNAL OF CARBOHYDRATE CHEMISTRY. 29(4). p.164-180
abstract
The cellulase mixture of Hypocrea jecorina (formerly Trichoderma reesei) contains a variety of exo- and endoglucanases that belong to different structural families. As such, these enzymes form an interesting model system to study the enzyme-ligand interactions in glycoside hydrolases. The nucleophilic carboxylate of retaining -glycosidases is believed to form a hydrogen bond with the 2-hydroxyl group of their substrate. Consequently, replacing this hydroxyl group with an amino group should result in a stronger electrostatic interaction and thus an increased affinity for the ligand. In this study, several modified cellobiosides were synthesized and evaluated as cellulase inhibitors. The introduction of an amino group was found to have an unpredictable effect on the inhibitory power of the ligands. However, the enzymes display a very high affinity for the corresponding 2-azido compounds, precursors in the synthetic route. The new ligand m-iodobenzyl 2-deoxy-2-azido--cellobioside even is the strongest inhibitor of cellobiohydrolase I known to date (KI= 1 M).
Please use this url to cite or link to this publication:
author
organization
alternative title
Synthesis and evaluation of 2-deoxy-2-amino-beta-cellobiosides as cellulase inhibitors
year
type
journalArticle (original)
publication status
published
subject
keyword
2-Amino-2-deoxy-cellobioside, TRICHODERMA-REESEI, Inhibition, Cellulase, Glycosidase, AZIDONITRATION, ENDOGLUCANASE, HYDROLYSIS, MECHANISMS, GLYCOSIDES, CLEAVAGE, GLUCOSE, ENZYMES
journal title
JOURNAL OF CARBOHYDRATE CHEMISTRY
J. Carbohydr. Chem.
volume
29
issue
4
pages
164 - 180
Web of Science type
Article
Web of Science id
000281313800002
JCR category
CHEMISTRY, ORGANIC
JCR impact factor
1.055 (2010)
JCR rank
36/56 (2010)
JCR quartile
3 (2010)
ISSN
0732-8303
DOI
10.1080/07328303.2010.508142
language
English
UGent publication?
yes
classification
A1
copyright statement
I have transferred the copyright for this publication to the publisher
id
1089300
handle
http://hdl.handle.net/1854/LU-1089300
date created
2010-12-17 16:14:02
date last changed
2016-12-19 15:46:17
@article{1089300,
  abstract     = {The cellulase mixture of Hypocrea jecorina (formerly Trichoderma reesei) contains a variety of exo- and endoglucanases that belong to different structural families. As such, these enzymes form an interesting model system to study the enzyme-ligand interactions in glycoside hydrolases. The nucleophilic carboxylate of retaining -glycosidases is believed to form a hydrogen bond with the 2-hydroxyl group of their substrate. Consequently, replacing this hydroxyl group with an amino group should result in a stronger electrostatic interaction and thus an increased affinity for the ligand. In this study, several modified cellobiosides were synthesized and evaluated as cellulase inhibitors. The introduction of an amino group was found to have an unpredictable effect on the inhibitory power of the ligands. However, the enzymes display a very high affinity for the corresponding 2-azido compounds, precursors in the synthetic route. The new ligand m-iodobenzyl 2-deoxy-2-azido--cellobioside even is the strongest inhibitor of cellobiohydrolase I known to date (KI= 1 M).},
  author       = {Desmet, Tom and Claeyssens, Marc and Piens, Kathleen and Nerinckx, Wim},
  issn         = {0732-8303},
  journal      = {JOURNAL OF CARBOHYDRATE CHEMISTRY},
  keyword      = {2-Amino-2-deoxy-cellobioside,TRICHODERMA-REESEI,Inhibition,Cellulase,Glycosidase,AZIDONITRATION,ENDOGLUCANASE,HYDROLYSIS,MECHANISMS,GLYCOSIDES,CLEAVAGE,GLUCOSE,ENZYMES},
  language     = {eng},
  number       = {4},
  pages        = {164--180},
  title        = {Synthesis and evaluation of 2-deoxy-2-amino-\ensuremath{\beta}-cellobiosides as cellulase inhibitors},
  url          = {http://dx.doi.org/10.1080/07328303.2010.508142},
  volume       = {29},
  year         = {2010},
}

Chicago
Desmet, Tom, Marc Claeyssens, Kathleen Piens, and Wim Nerinckx. 2010. “Synthesis and Evaluation of 2-deoxy-2-amino-β-cellobiosides as Cellulase Inhibitors.” Journal of Carbohydrate Chemistry 29 (4): 164–180.
APA
Desmet, Tom, Claeyssens, M., Piens, K., & Nerinckx, W. (2010). Synthesis and evaluation of 2-deoxy-2-amino-β-cellobiosides as cellulase inhibitors. JOURNAL OF CARBOHYDRATE CHEMISTRY, 29(4), 164–180.
Vancouver
1.
Desmet T, Claeyssens M, Piens K, Nerinckx W. Synthesis and evaluation of 2-deoxy-2-amino-β-cellobiosides as cellulase inhibitors. JOURNAL OF CARBOHYDRATE CHEMISTRY. 2010;29(4):164–80.
MLA
Desmet, Tom, Marc Claeyssens, Kathleen Piens, et al. “Synthesis and Evaluation of 2-deoxy-2-amino-β-cellobiosides as Cellulase Inhibitors.” JOURNAL OF CARBOHYDRATE CHEMISTRY 29.4 (2010): 164–180. Print.