On the conformation of 5-substituted uridines as studied by proton magnetic resonance | Zendy

Wolfgang Uhl | Zendy; Josef Reiner | Zendy; Hans Günter Gassen | Zendy

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On the conformation of 5-substituted uridines as studied by proton magnetic resonance

Author(s) -

Wolfgang Uhl,

Josef Reiner,

Hans Günter Gassen

Publication year - 1983

Publication title -

nucleic acids research

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 9.008

H-Index - 537

eISSN - 1362-4954

pISSN - 0305-1048

DOI - 10.1093/nar/11.4.1167

Subject(s) - conformational isomerism , proton magnetic resonance , alkane stereochemistry , stereochemistry , proton , resonance (particle physics) , crystallography , nuclear magnetic resonance spectroscopy , nuclear magnetic resonance , chemistry , molecule , crystal structure , organic chemistry , physics , quantum mechanics , particle physics

The proton magnetic resonance (pmr) spectra of 10 basemodified uridine derivatives x5Urd have been measured at 3 degrees, 30 degrees, and 60 degrees C in order to correlate the electronic effects of different substituents with the molecular conformation of the respective nucleosides. The results presented demonstrate the close relation between conformational parameters and the electron-affinity of the substituents as reflected by their Hammett constants. Going from electron-donating to electron-accepting groups, the portion of N-conformer in the ribose N in equilibrium S equilibrium increases from 44% to about 90%. In addition the percentage of gauche-gauche rotamer as measured for the exocyclic groups changes from about 30% in nh52Urd to more than 80% in no52Urd.

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