Abstract
The mechanism of the acid-catalyzed anomerization of 1-O-acetyl-2,3,5-O-benzoyi-alpha- and -beta-L-ribofuranoses in different acetic acid-acetic anhydride mixtures was investigated. The progress of the reactions was followed by NMR spectroscopy and the rate constants for the reactions were determined by the use of a kinetic model. The site of anomeric activation was clarified by the use of (13)C-labeled acetic acid and acetic anhydride, respectively, proving that the anomerization takes place by exocyclic C-O cleavage, thus ruling out anomerization via acyclic intermediates. The role of the acetyl cation as the catalytically active species was further verified. (C) 2009 Elsevier Ltd. All rights reserved.
| Original language | Undefined/Unknown |
|---|---|
| Pages (from-to) | 1102–1109 |
| Number of pages | 8 |
| Journal | Carbohydrate Research |
| Volume | 344 |
| Issue number | 9 |
| DOIs | |
| Publication status | Published - 2009 |
| MoE publication type | A1 Journal article-refereed |
Keywords
- (13)C Labeling
- Anomerization
- L-Ribose
- Reaction kinetics