Synonym
2-Aminoadenosine; 2096-10-8; 2-Amine adenosine; Adenosine, 2-amino-;
IUPAC/Chemical Name
(2R,3R,4S,5R)-2-(2,6-diamino-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
InChi Key
ZDTFMPXQUSBYRL-UUOKFMHZSA-N
InChi Code
InChI=1S/C10H14N6O4/c11-7-4-8(15-10(12)14-7)16(2-13-4)9-6(19)5(18)3(1-17)20-9/h2-3,5-6,9,17-19H,1H2,(H4,11,12,14,15)/t3-,5-,6-,9-/m1/s1
SMILES Code
OC[C@@H]1[C@H]([C@H]([C@H](N2C=NC3=C(N=C(N)N=C32)N)O1)O)O
Appearance
To be determined
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
282.26
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Grzeskowiak K, Webb TR, Orgel LE. Template-directed synthesis with
2-aminoadenosine. J Mol Evol. 1984;21(1):81-3. doi: 10.1007/BF02100631. PMID:
6442362.
2: Kore AR, Parmar G, Reddy S. An efficient process for synthesis of 2'-O-methyl
and 3'-O-methyl guanosine from 2-aminoadenosine using diazomethane and the
catalyst stannous chloride. Nucleosides Nucleotides Nucleic Acids. 2006
Mar;25(3):307-14. doi: 10.1080/15257770500544529. PMID: 16629123.
3: Pujari SS, Leonard P, Seela F. Oligonucleotides with "clickable" sugar
residues: synthesis, duplex stability, and terminal versus central interstrand
cross-linking of 2'-O-propargylated 2-aminoadenosine with a bifunctional azide.
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2-aminoadenosine and isoguanosine: synthesis, deamination and tautomerism. Org
Biomol Chem. 2007 Sep 21;5(18):3034-45. doi: 10.1039/b708736e. Epub 2007 Aug 14.
PMID: 17728871.
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2-aminoadenosine, guanosine, and xanthosine: glycosylation of
pyrrolo[2,3-d]pyrimidines with 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose. J
Org Chem. 2006 Jan 6;71(1):81-90. doi: 10.1021/jo0516640. PMID: 16388621.
6: Lamm GM, Blencowe BJ, Sproat BS, Iribarren AM, Ryder U, Lamond AI. Antisense
probes containing 2-aminoadenosine allow efficient depletion of U5 snRNP from
HeLa splicing extracts. Nucleic Acids Res. 1991 Jun 25;19(12):3193-8. doi:
10.1093/nar/19.12.3193. PMID: 1648201; PMCID: PMC328310.
7: Kaloudis P, D'Angelantonio M, Guerra M, Gimisis T, Mulazzani QG,
Chatgilialoglu C. One-electron reduction of 8-bromo-2-aminoadenosine in the
aqueous phase: radiation chemical and DFT studies of the mechanism. J Phys Chem
B. 2008 Apr 24;112(16):5209-17. doi: 10.1021/jp800480f. Epub 2008 Mar 29. PMID:
18373377.
8: Rinkel LJ, Mellema JR, van der Marel GA, van Boom JH, Altona C. Influence of
2-aminoadenosine, A', on the conformational behaviour of d(T-A'-T-A'). A one-
dimensional proton NMR study at 300 MHz and 500 MHz. Eur J Biochem. 1986 Jan
15;154(2):259-65. doi: 10.1111/j.1432-1033.1986.tb09391.x. PMID: 3002796.
9: Ueeda M, Thompson RD, Arroyo LH, Olsson RA. 2-aralkoxyadenosines: potent and
selective agonists at the coronary artery A2 adenosine receptor. J Med Chem.
1991 Apr;34(4):1340-4. doi: 10.1021/jm00108a015. PMID: 2016708.
