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Carbon‐13 NMR spectra of nucleoside 3′,5′‐cyclic phosphates. Proposition for revised signal assignments
Author(s) -
Uesugi Seiichi,
Tanaka Sumie,
Ikehara Morio
Publication year - 1979
Publication title -
organic magnetic resonance
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0030-4921
DOI - 10.1002/mrc.1270120303
Subject(s) - nucleoside , phosphate , ribonucleoside , sugar phosphates , chemistry , thymidine , chemical shift , stereochemistry , carbon 13 nmr , spectral line , nmr spectra database , organic chemistry , rna , biochemistry , dna , physics , astronomy , gene
On the basis of the data obtained from 13 C NMR spectra of 8,2′‐S‐cycloadenosine 3′,5′‐cyclic phosphate and other nucleoside 3′,5′‐cyclic phosphate analogues, it is suggested that the published assignments of the C‐3′ and C‐4′ signals in nucleoside 3′,5′‐cyclic phosphates should be reversed. According to the revised assignments, C‐4′, which is fixed very closely to the diesterified phosphate group is markedly shielded (−12.5 to −15 ppm), and the C‐3′ signal shows a downfield shift (+6 to +8 ppm) which is comparable to that for the C‐5′ signal, for all compounds so far measured when compared with the chemical shifts for the corresponding nucleosides. The 3′,5′‐cyclic phosphates of thymidine and 8,2′‐S‐cycloadenosine, which have no α‐OH group on C‐2′, show similar chemical shift changes for the corresponding sugar carbons which are different from those observed for ribonucleoside derivatives.