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Proton magnetic resonance study of the conformations of 3′,5′‐ O ‐(di‐ tert ‐butylsilanediyl) nucleosides
Author(s) -
Katsura Tatsuo,
Ueno Katsuhiko,
Furusawa Kiyotaka
Publication year - 1993
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.1260311202
Subject(s) - chemistry , furanose , glycosidic bond , nuclear magnetic resonance spectroscopy , deoxyadenosine , stereochemistry , proton magnetic resonance , nucleotide , alkane stereochemistry , proton , adenosine , crystallography , nuclear magnetic resonance , ring (chemistry) , crystal structure , organic chemistry , biochemistry , physics , quantum mechanics , gene , enzyme
The solution conformations of nine 3′,5′‐ O ‐(di‐ tert ‐butylsilanediyl) nucleosides, new sila analogues of cyclic nucleotides, were studied by proton NMR spectroscopy. The furanose rings of all the compounds studied are forced to take on the C‐3′‐ endo conformation by the 3′,5′‐cyclization. The conformations at the glycosidic bond of the adenosine and deoxyadenosine derivatives were determined as mixtures of syn and anti conformations by the DESERT method; the fractions of anti conformation for these derivatives were 0.58 and 0.41, respectively.