Click fleximers: a modular approach to purine base-expanded ribonucleoside analogues.

Area of Science:

• Medicinal Chemistry
• Organic Synthesis
• Computational Chemistry

Background:

• Purine nucleobase mimics are crucial in developing novel therapeutic agents.
• Expanding the structural diversity of nucleobase analogues can lead to compounds with unique properties.

Purpose of the Study:

• To synthesize novel nucleoside analogues using 4-(5-pyrimidinyl)-1,2,3-triazole aglycons as expanded purine mimics.
• To explore the potential for fluorescence and metal-binding properties in these novel analogues.
• To investigate the structural and conformational preferences of the synthesized purine analogues.

Main Methods:

• Copper-catalyzed azide-alkyne Huisgen cycloaddition reaction.
• Synthesis utilizing ribosyl azide and 5-alkynylpyrimidines.
• Computational studies including conformational analysis.

Main Results:

• Successfully synthesized nucleoside analogues incorporating 4-(5-pyrimidinyl)-1,2,3-triazole aglycons.
• Prepared analogues with fluorescence and potential metal-binding characteristics based on alkyne selection.
• Computational studies indicated a preference for coplanar arrangements and anti-glycosidic conformers.

Conclusions:

• The study demonstrates a versatile method for synthesizing expanded purine nucleobase mimics.
• The synthesized nucleoside analogues show promise for applications in medicinal chemistry and materials science.
• Conformational analysis provides insights into the structural stability and preferred orientations of these novel compounds.