Science of Synthesis

Liang, Y.; Wen, Z.; Cabrera, M.; Howlader, A. H.; Wnuk, S. F., Science of Synthesis Knowledge Updates, (2020) 1, 309.

Azido-modified purines have been utilized for decades as potential anticancer and antiviral agents or prodrugs,[‌232‌–‌234‌] and as photoaffinity probes for DNA/RNA studies.[‌235‌,‌236‌] Recently, they have gained attention as effective substrates in click reactions for biological probes and imaging agents.[‌237‌–‌241‌] Azidopurines can tautomerize to stable tetrazoles depending on the position of the azide on the purine system, electronic nature of substituents, temperature, and solvent type.[‌242‌,‌243‌] The azido–tetrazole tautomerization has been studied in purines[‌243‌,‌244‌] and has important implications in the reactivity toward click reactions.[‌236‌,‌238‌]

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