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CAS 31966-52-6

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8-azidoadenosine 3':5'-cyclic*monophosphate free

Description:
8-Azidoadenosine 3',5'-cyclic monophosphate (often abbreviated as 8-Azido-cAMP) is a nucleotide analog that serves as a potent biochemical tool in research, particularly in studies involving cyclic AMP (cAMP) signaling pathways. This compound features an azido group at the 8-position of the adenine base, which enhances its reactivity and allows for photochemical activation. It is characterized by its cyclic phosphate structure, which is crucial for mimicking the natural cAMP molecule in biological systems. 8-Azido-cAMP is known to interact with various proteins, including protein kinases, and can influence cellular processes such as gene expression, cell proliferation, and differentiation. Its unique properties make it valuable for probing the mechanisms of cAMP-mediated signaling and for developing potential therapeutic strategies. Additionally, due to its azido group, it can be utilized in click chemistry applications, facilitating the conjugation of biomolecules for further study. Overall, 8-Azido-cAMP is a significant compound in biochemical research, providing insights into cellular signaling mechanisms.
Formula:C10H11N8O6P
InChI:InChI=1/C10H11N8O6P/c11-7-4-8(14-2-13-7)18(10(15-4)16-17-12)9-5(19)6-3(23-9)1-22-25(20,21)24-6/h2-3,5-6,9,19H,1H2,(H,20,21)(H2,11,13,14)/t3-,5-,6-,9-/m1/s1
SMILES:C1[C@@H]2[C@H]([C@H]([C@H](n3c4c(c(N)ncn4)nc3N=[N+]=[NH-])O2)O)OP(=O)(O)O1
Synonyms:
  • 8-Azidoadenosine-3',5'-monophosphate
  • 8-Azido-cyclic AMP
  • 8-Azidoadenosine cyclic 3',5'-(hydrogen phosphate)
  • 8-N3-cAMP
  • Adenosine, 8-azido-, cyclic 3',5'-(hydrogen phosphate)
  • (4aR,6R,7R,7aS)-6-(6-amino-8-azido-9H-purin-9-yl)tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol 2-oxide
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