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



: MIKHAILOV SN, OIVANEN M, OKSMAN P, LONNBERG H

Publisher: AMER CHEMICAL SOC

: 1992

Journal of Organic Chemistry

JOURNAL OF ORGANIC CHEMISTRY

: J ORG CHEM

: 57

: 15

: 4122

: 4126

: 5

: 0022-3263

DOI: https://doi.org/10.1021/jo00041a014


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.



Last updated on 2025-13-10 at 11:35