A1 Refereed original research article in a scientific journal
KINETICS FOR THE ACID-CATALYZED HYDROLYSIS OF O-BRIDGED, S-BRIDGED AND N-BRIDGED 5',8-CYCLONUCLEOSIDES RELATED TO ADENOSINE
Authors: KARPEISKY A, ZAVGORODNY S, HOTOKKA M, OIVANEN M, LONNBERG H
Publisher: ROYAL SOC CHEMISTRY
Publication year: 1994
Journal:: Royal Society of Chemistry. Journal: Perkin Transactions 2
Journal name in source: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2
Journal acronym: J CHEM SOC PERK T 2
Issue: 4
First page : 741
Last page: 744
Number of pages: 4
ISSN: 0300-9580
DOI: https://doi.org/10.1039/p29940000741
Abstract
Kinetics of the acid-catalysed hydrolysis of O-5',8-cycloadenosine, S-5',8-cyclo-5'-thioadenosine and N-5',8-cyclo-5'-amino-5'-deoxyadenosine have been studied. the S- and N-bridged cyclonucleosides are hydrolysed exclusively by the rupture of the N-glycosidic bond, white the O-bridged compound undergoes concurrent cleavage of the N-glycosidic and 5',8-cyclo linkages, the proportion of the former reaction being markedly increased with increasing temperature. The conformations of the same cyclonucleosides have been elucidated by molecular modelling (SYBYL) and H-1 NMR spectroscopy. The effect of the sugar ring puckering on the hydrolytic stability is discussed.
Kinetics of the acid-catalysed hydrolysis of O-5',8-cycloadenosine, S-5',8-cyclo-5'-thioadenosine and N-5',8-cyclo-5'-amino-5'-deoxyadenosine have been studied. the S- and N-bridged cyclonucleosides are hydrolysed exclusively by the rupture of the N-glycosidic bond, white the O-bridged compound undergoes concurrent cleavage of the N-glycosidic and 5',8-cyclo linkages, the proportion of the former reaction being markedly increased with increasing temperature. The conformations of the same cyclonucleosides have been elucidated by molecular modelling (SYBYL) and H-1 NMR spectroscopy. The effect of the sugar ring puckering on the hydrolytic stability is discussed.
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