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| Content Provider | World Health Organization (WHO)-Global Index Medicus |
|---|---|
| Author | Amorim, Luis Marrot, Jérôme Rauter, Amélia P. Sollogoub, Matthieu Marcelo, Filipa Blériot, Yves Bols, Mikael Jiménez-barbero, Jesús Rousseau, Cyril Nieto, Lidia |
| Description | Author Affiliation: Amorim L ( UPMC Univ Paris 06, Institut Parisien de Chimie Moléculaire (UMR 7201), FR 2769, C181, 4 place Jussieu, 75005 Paris, France.) |
| Abstract | The effect of a $^{2,5}B$ boat conformation on xyloside reactivity has been investigated by studying the hydrolysis and glycosylation of a series of synthetic xyloside analogues based on a 2-oxabicyclo[2.2.2]octane framework, which forces the xylose analogue to adopt a $^{2,5}B$ conformation. The locked β-xylosides were found to hydrolyze 100–1200 times faster than methyl β-D-xylopyranoside, whereas the locked α-xylosides hydrolyzed up to $2×10^{4}$ times faster than methyl α-D-xylopyranoside. A significant rate enhancement was also observed for the glycosylation reaction. The high reactivity of these conformers can be related to the imposition of a $^{2,5}B$ conformation, which approximates a transition state (TS) boat conformation. In this way, the energy penalty required to go from the chair to the TS conformation is already paid. These results parallel and support the observation that the GH-11 xylanase family force their substrate to adopt a $^{2,5}B$ conformation to achieve highly efficient enzymatic glycosidic bond hydrolysis. |
| ISSN | 09476539 |
| e-ISSN | 15213765 |
| Journal | Chemistry - A European Journal |
| Issue Number | 26 |
| Volume Number | 17 |
| Language | English |
| Publisher | Wiley-VCH;ChemPubSoc Europe |
| Publisher Date | 2011-06-20 |
| Publisher Place | Germany |
| Access Restriction | Open |
| Subject Keyword | Glycosides Chemistry Carbohydrate Conformation Catalysis Crystallography, X-Ray Chemical Synthesis Glycosylation Hydrolysis Molecular Structure Stereoisomerism Structure-Activity Relationship Research Support, Non-U.S. Gov't |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Catalysis |
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