A1 Refereed original research article in a scientific journal
HYDROLYSIS OF 2'-C-METHYLURIDINE AND 3'-C-METHYLURIDINE 2',3'-CYCLIC MONOPHOSPHATES AND INTERCONVERSION AND DEPHOSPHORYLATION OF THE RESULTING 2'-MONOPHOSPHATE AND 3'-MONOPHOSPHATE - COMPARISON WITH THE REACTIONS OF URIDINE MONOPHOSPHATES
Authors: MIKHAILOV SN, OIVANEN M, OKSMAN P, LONNBERG H
Publisher: AMER CHEMICAL SOC
Publication year: 1992
Journal:: Journal of Organic Chemistry
Journal name in source: JOURNAL OF ORGANIC CHEMISTRY
Journal acronym: J ORG CHEM
Volume: 57
Issue: 15
First page : 4122
Last page: 4126
Number of pages: 5
ISSN: 0022-3263
DOI: https://doi.org/10.1021/jo00041a014
Abstract
2',3'-Cyclic monophosphates of 2'- and 3'-C-methyluridines have been prepared and shown to hydrolyze to a mixture of the corresponding 2'- and 3'-monophosphates. The predominant product isomer is the one having the tertiary hydroxyl group phosphorylated, but on longer treatment a phosphate migration from the tertiary to secondary hydroxyl function takes place. Hydrolytic dephosphorylation competes with the phosphate migration, the tertiary hydroxyl group being dephosphorylated 1 order of magnitude faster than the secondary one. Kinetics of the partial reactions have been described and compared to the data obtained with uridine 2',3'-cyclic monophosphate. The tertiary monophosphate has been shown to be exceptionally susceptible to nucleophilic attack of the neighboring hydroxyl group.
2',3'-Cyclic monophosphates of 2'- and 3'-C-methyluridines have been prepared and shown to hydrolyze to a mixture of the corresponding 2'- and 3'-monophosphates. The predominant product isomer is the one having the tertiary hydroxyl group phosphorylated, but on longer treatment a phosphate migration from the tertiary to secondary hydroxyl function takes place. Hydrolytic dephosphorylation competes with the phosphate migration, the tertiary hydroxyl group being dephosphorylated 1 order of magnitude faster than the secondary one. Kinetics of the partial reactions have been described and compared to the data obtained with uridine 2',3'-cyclic monophosphate. The tertiary monophosphate has been shown to be exceptionally susceptible to nucleophilic attack of the neighboring hydroxyl group.
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