Stereoelectronic effects of modified purine bases on the sugar conformation of nucleosides: pyrrolo[2,3-d]pyrimidines

Autor(en): Rosemeyer, H 
Seela, F
Stichwörter: 500-MHZ H-1-NMR SPECTROSCOPY; C-NUCLEOSIDES; Chemistry; Chemistry, Organic; Chemistry, Physical; COUPLING-CONSTANTS; DNA; DRIVE; DUPLEX STABILITY; OLIGONUCLEOTIDES; PENTOFURANOSE MOIETY; PROTON MAGNETIC-RESONANCE; PSEUDOROTATIONAL EQUILIBRIUM
Erscheinungsdatum: 1997
Herausgeber: ROYAL SOC CHEMISTRY
Journal: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2
Ausgabe: 11
Startseite: 2341
Seitenende: 2345
Zusammenfassung: 
Steric and stereoelectronic effects of 7- and 8-substituents of 7-deaza-2'-deoxy-adenosine and -guanosine on the dynamic sugar puckering as well as on the conformation about the C(4')-C(5') bond have been studied, (i) The higher the electron-attracting effect of the substituents, the more the N reversible arrow S (North reversible arrow South) equilibrium of the pentofuranose moiety is biased towards the N-conformation, (ii) The higher the electron-withdrawing effect of the 7-substituents, the higher the gamma((+)g) (+sc) rotamer population around the C(4')-C(5') bond. The interdependencies of the conformational equilibria of 7-deazapurine nucleosides and their influence on oligonucleotide secondary structures are discussed.
ISSN: 03009580
DOI: 10.1039/a702501g

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