N6-Acetyladenosine
N6-Acetyladenosine, a remarkable biomedical commodity, manifests its indispensable role in the oncological landscape. Holding the prowess as a nucleoside analog, it exerts a profound hindrance upon the inexorable growth of malignant cells, effectively triggering their untimely demise through apoptosis induction. The intrinsic antitumor attributes exhibited by N6-Acetyladenosine unmask its promising potential, thereby rendering it a plausible candidate for incorporation into targeted chemotherapy protocols capable of subduing a diverse array of tumor classifications.
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Synonyms
Adenosine, N-acetyl-; N-Acetyladenosine; N6-acetyl-adenosine; N-(9-((2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)acetamide; N-(9-β-D-Ribofuranosyl-9-H-purin-6-yl)-acetamide
IUPAC Name
N-[9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]acetamide
Molecular Formula
C12H15N5O5
Canonical SMILES
CC(=O)NC1=C2C(=NC=N1)N(C=N2)C3C(C(C(O3)CO)O)O
InChI
InChI=1S/C12H15N5O5/c1-5(19)16-10-7-11(14-3-13-10)17(4-15-7)12-9(21)8(20)6(2-18)22-12/h3-4,6,8-9,12,18,20-21H,2H2,1H3,(H,13,14,16,19)/t6-,8-,9-,12-/m1/s1
InChIKey
SLLVJTURCPWLTP-WOUKDFQISA-N
Solubility
Soluble in DMF, DMSO, Ethanol, Methanol
Appearance
White to Off-white Powder
Chemical Structure:
Reference Reading
1. N6-Acetyladenosine: a new modified nucleoside from Methanopyrus kandleri tRNA
Anselm Sauerwald, Devarasetty Sitaramaiah, James A McCloskey, Dieter Söll, Pamela F Crain. FEBS Lett. 2005 May 23;579(13):2807-10. doi: 10.1016/j.febslet.2005.04.014.
Post-transcriptionally modified nucleosides are constituents of transfer RNA (tRNA) that are known to influence tertiary structure, stability and coding properties. Modifications in unfractionated tRNA from the phylogenetically unique archaeal methanogen Methanopyrus kandleri (optimal growth temperature 98 degrees C) were studied using liquid chromatography-mass spectrometry to establish the extent to which they might differ from those of other methanogens. The exceptionally diverse population of nucleosides included four new nucleosides of unknown structure, and one that was characterized as N(6)-acetyladenosine, a new RNA constituent. The nucleoside modification pattern in M. kandleri tRNA is notably different from that of other archaeal methanogens, and is closer to that of the thermophilic crenarchaeota.
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