Reaction kinetics and mechanism of acid-catalyzed anomerization of 1-O-acetyl-2,3,5-tri-O-benzoyl-L-ribofuranose

A1 Journal article (refereed)


Internal Authors/Editors


Publication Details

List of Authors: Forsman JJ, Warna J, Murzin DY, Leino R
Publisher: ELSEVIER SCI LTD
Publication year: 2009
Journal: Carbohydrate Research
Journal acronym: CARBOHYD RES
Volume number: 344
Issue number: 9
Start page: 1102
End page: 1109
Number of pages: 8
ISSN: 0008-6215


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.


Keywords

(13)C Labeling, Anomerization, L-Ribose, Reaction kinetics

Last updated on 2019-21-09 at 02:56