1-Deaza-3′-O-methyladenosine: A Nucleoside with theSyn-conformation in the Solid State and in Solution
- Resource Type
- Authors
- Hans Reuter; Igor A. Mikhailopulo; Guide Kastner; Frank Seela; Harald Debelak
- Source
- Nucleosides and Nucleotides. 17:729-744
- Subject
- Hydrogen bond
Stereochemistry
Chemistry
Dihedral angle
Carbon-13 NMR
Biochemistry
Crystallography
chemistry.chemical_compound
Intramolecular force
Genetics
Moiety
Glycosyl
Single crystal
Nucleoside
- Language
- ISSN
- 0732-8311
The 2′-O-methyl (2) and the 3′-O-methyl (3) derivatives of 1-deazaadenosine (1) were prepared. Single crystal X-ray analysis as well as 1H and 13C NMR studies were performed on the 3′-O-methyl-1-deazaadenosine 3. In the solid state, the glycosyl torsion angle (χ = 64.7°) is in the syn-range which is caused by an intramolecular (5′)CH2OH…N(3) hydrogen bond. The ribofuranose moiety adopts a 2 E (C-3′-exo; S) conformation and the orientation of the exocyclic C(4′)-C(5′) bond is + sc (γ(+)g). The conformation in solution was found to be very similar to that in solid state. Whereas the 2′-O-methyl derivative of 1 is a strong inhibitor of adenosine deaminase the 3′-O-methyl derivative is neither inhibitor nor substrate.