A1 Refereed original research article in a scientific journal
DIOXOLANE NUCLEOSIDES AND THEIR PHOSPHONATE DERIVATIVES - SYNTHESIS AND HYDROLYTIC STABILITY
Authors: EFIMTSEVA EV, MIKHAILOV SN, MESHKOV S, HANKAMAKI T, OIVANEN M, LONNBERG H
Publisher: ROYAL SOC CHEMISTRY
Publication year: 1995
Journal:: Journal of the Chemical Society. Perkin transactions 1
Journal name in source: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
Journal acronym: J CHEM SOC PERK T 1
Issue: 11
First page : 1409
Last page: 1415
Number of pages: 7
ISSN: 0300-922X
DOI: https://doi.org/10.1039/p19950001409
Abstract
Several new nucleoside (12-15):and nucleoside phosphonate (27-30) analogues derived from (+/-)-cis-and -trans-2-hydroxymethyl-4-methyl-1,3-dioxolane have been prepared and their configurations assigned by H-1 NMR spectroscopy. First-order rate constants for the acid-catalysed hydrolysis of the dioxolane ring have been determined at different hydronium ion concentrations. The phosphonate group accelerates the hydrolysis at pH > 2 by 2 orders of magnitude, while at pH < 1 the hydrolytic stabilities of the nucleoside analogues and their phosphonate derivatives are comparable. The possible reasons for this rate-enhancement are discussed on the basis of the reaction mechanism.
Several new nucleoside (12-15):and nucleoside phosphonate (27-30) analogues derived from (+/-)-cis-and -trans-2-hydroxymethyl-4-methyl-1,3-dioxolane have been prepared and their configurations assigned by H-1 NMR spectroscopy. First-order rate constants for the acid-catalysed hydrolysis of the dioxolane ring have been determined at different hydronium ion concentrations. The phosphonate group accelerates the hydrolysis at pH > 2 by 2 orders of magnitude, while at pH < 1 the hydrolytic stabilities of the nucleoside analogues and their phosphonate derivatives are comparable. The possible reasons for this rate-enhancement are discussed on the basis of the reaction mechanism.
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