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Mercuration effects on nucleoside chemical shifts: 15 N and 13 C NMR studies of methylmercury(II) ion addition to cytidine‐3′‐monophosphate and guanosine‐5′‐monophosphate
Author(s) -
Buchanan G. W.,
Bell M.J.
Publication year - 1986
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.1260240604
Subject(s) - chemistry , guanosine , cytidine , guanosine monophosphate , deprotonation , nucleoside , chemical shift , fluorine 19 nmr , stereochemistry , nuclear magnetic resonance spectroscopy , cyclic guanosine monophosphate , nucleotide , ion , organic chemistry , biochemistry , enzyme , nitric oxide , gene
Abstract Methylmercuration of cytidine‐3′‐monophosphate is shown to occur at the N‐3 site, resulting in a substantial upfield shift in the 15 N resonance of this nitrogen. For guanosine‐5′‐monophosphate the 15 N NMR data show N‐1 to be the site of complexation of CH 3 Hg + at pH 8. The large downfield shift observed for N‐1 as a result of this binding is explained in terms of a concomitant deprotonation phenomenon. Changes in 13 C NMR chemical shifts on methylmercuration are less pronounced, but consistent with these binding sites.