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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
Tekijät: MIKHAILOV SN, OIVANEN M, OKSMAN P, LONNBERG H
Kustantaja: AMER CHEMICAL SOC
Julkaisuvuosi: 1992
Lehti:: Journal of Organic Chemistry
Tietokannassa oleva lehden nimi: JOURNAL OF ORGANIC CHEMISTRY
Lehden akronyymi: J ORG CHEM
Vuosikerta: 57
Numero: 15
Aloitussivu: 4122
Lopetussivu: 4126
Sivujen määrä: 5
ISSN: 0022-3263
DOI: https://doi.org/10.1021/jo00041a014
Tiivistelmä
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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