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Oligonucleosides with a Nucleobase‐Including Backbone, Part 7
Author(s) -
Bhardwaj Punit Kumar,
Vasella Andrea
Publication year - 2002
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(200203)85:3<699::aid-hlca699>3.0.co;2-n
Subject(s) - chemistry , nucleobase , intramolecular force , dimer , unit (ring theory) , stereochemistry , folding (dsp implementation) , nucleotide , solvent , hydrogen bond , crystallography , molecule , dna , organic chemistry , biochemistry , mathematics education , mathematics , electrical engineering , gene , engineering
The conformational analysis of 7 was carried out in (D 6 )DMSO and in mixtures of (D 6 )DMSO and CDCl 3 to evaluate the syn / anti conformations, relevant to the pairing propensity of this type of nucleotide analogue. The HO−C(5′) of unit I and of unit II of the dimer 7 form an intramolecular H‐bond to N(3). In (D 6 )DMSO, the C(5′)−OH⋅⋅⋅N(3) H‐bond in unit I is partially broken, while that in unit II persists to a larger extent. The syn conformation prevails for unit I and particularly for unit II. The furanosyl moieties adopt predominantly a 2′ ‐endo conformation that is largely independent of the solvent.