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CAS 29984-33-6

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ara-AMP

Description:
Ara-AMP, or 2'-deoxy-2'-arabinofuranosyladenosine monophosphate, is a nucleoside analog characterized by its unique arabinose sugar configuration, which distinguishes it from the more common ribose and deoxyribose sugars found in nucleotides. This compound features an adenine base linked to a 2'-arabinofuranosyl moiety, contributing to its structural and functional properties. Ara-AMP is known for its role in antiviral and anticancer research, as it can interfere with nucleic acid synthesis and exhibit cytotoxic effects on certain cell types. The presence of the arabinose sugar can enhance its stability and bioavailability compared to other nucleoside analogs. Additionally, ara-AMP can be phosphorylated to its triphosphate form, which is crucial for its mechanism of action in inhibiting viral replication or cancer cell proliferation. Its unique structure and biological activity make it a subject of interest in medicinal chemistry and pharmacology, particularly in the development of therapeutic agents targeting viral infections and malignancies.
Formula:C10H14N5O7P
InChI:InChI=1S/C10H14N5O7P/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(22-10)1-21-23(18,19)20/h2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,20)/t4-,6-,7+,10-/m1/s1
InChI key:InChIKey=UDMBCSSLTHHNCD-UHTZMRCNSA-N
SMILES:O[C@@H]1[C@H](N2C=3C(N=C2)=C(N)N=CN3)O[C@H](COP(=O)(O)O)[C@H]1O
Synonyms:
  • 5′-Arabinosyladenine monophosphate
  • 9-(5-O-Phosphono-β-<span class="text-smallcaps">D</span>-arabinofuranosyl)-9H-purin-6-amine
  • 9-(5-O-phosphonato-beta-D-arabinofuranosyl)-9H-purin-6-amine
  • 9-(5-O-phosphono-beta-D-arabinofuranosyl)-9H-purin-6-amine
  • 9-β-<span class="text-smallcaps">D</span>-Arabinofuranosyl AMP
  • 9-β-<span class="text-smallcaps">D</span>-Arabinofuranosyladenine 5′-monophosphate
  • 9-β-<span class="text-smallcaps">D</span>-Arabinofuranosyladenine 5′-phosphate
  • 9-β-<span class="text-smallcaps">D</span>-Arabinofuranosyladenine monophosphate
  • 9-β-D-Arabinofuranosyl-adenine-5'-monophosphate
  • 9-β-D-Arabinofuranosyl-adenine-5'-monophosphate,disodium salt
  • See more synonyms
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