5-Methyl-6-aza-2'-deoxyisocytidine

Area of Science:

• Crystallography
• Molecular Biology
• Organic Chemistry

Background:

• Understanding nucleoside analogs is crucial for drug discovery.
• The specific compound 3-amino-2-(2-deoxy-beta-D-erythro-pentofuranosyl)-6-methyl-1,2,4-triazin-5(2H)-one is a modified nucleoside with potential biological activity.
• Detailed structural analysis provides insights into molecular interactions and potential applications.

Purpose of the Study:

• To elucidate the three-dimensional structure of 3-amino-2-(2-deoxy-beta-D-erythro-pentofuranosyl)-6-methyl-1,2,4-triazin-5(2H)-one.
• To characterize the conformation of the N-glycosidic bond and the sugar pucker.
• To describe the crystal packing and intermolecular interactions.

Main Methods:

• Single-crystal X-ray diffraction analysis was performed.
• The molecular structure was determined and refined.
• Conformational analysis of the glycosidic bond and sugar ring was conducted.

Main Results:

• The N-glycosidic bond adopts a high-anti conformation.
• The 2-deoxyribofuranosyl moiety exhibits a North sugar pucker ((2)T(3)).
• The exocyclic C-C bond orientation is ap (gauche, trans).
• Crystal packing reveals nucleobases parallel to the ac plane, linked by hydrogen bonds.

Conclusions:

• The study provides a precise structural definition of the title compound.
• The determined conformation and packing are essential for understanding its chemical properties and potential biological interactions.
• This structural data can inform the design of related nucleoside analogs for therapeutic purposes.