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Carbon‐13 n.m.r. studies of purines and 8‐azapurines in basic aqueous medium
Author(s) -
Purnell Linda Goodrich,
Hodgson Derek J.
Publication year - 1977
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.1270100102
Subject(s) - purine metabolism , hypoxanthine , xanthine , guanine , chemistry , aqueous solution , purine , stereochemistry , aqueous medium , medicinal chemistry , nucleotide , organic chemistry , biochemistry , enzyme , gene
The 13 C n.m.r. spectra of a variety of purines and 8‐azapurines have been studied in aqueous basic medium; the shifts were measured using dioxane as reference, and corrected to the TMS scale. The compounds studied include adenine, hypoxanthine, 6‐mercaptopurine, guanine, xanthine, 8‐azaadenine, 8‐azahypoxanthine, 8‐azaguanine, 8‐azaxanthine, and 2‐thio‐8‐azaxanthine. Resonances were assigned using noise‐decoupling, selective deuteration at the 8‐position of purines, and coupled spectra. The general effect of changing from a purine to its 8‐aza analog is to produce a downfield shift of C‐2, C‐5, and C‐6 and an upfield shift of C‐4.