2140-79-6 , 2'-O-Methyladenosine,
CAS:2140-79-6
MFCD00056002
C11H15N5O4 /281.27
white to off-white powder.
2'-O-Methyladenosine (2'-OMeA) is a nucleoside that is a low-energy analog of adenosine. It has been shown to be an effective inhibitor of protein synthesis in vitro, by inhibiting RNA polymerase in the process of transcription. 2'-OMeA has also been shown to inhibit virus replication in vitro and to have potent inhibitory activity against human immunodeficiency virus type 1 (HIV-1). 2'-OMeA inhibits viral replication by binding to the viral ribonucleotide reductase enzyme and blocking the conversion of ribonucleotides into deoxyribonucleotides. The chemical structures of 2'-OMeA are similar to those found in fatty acids and can be detected using chemical ionization mass spectroscopy. The sequence for 2'-OMeA was determined through sequencing methods including NMR spectroscopy and nuclear magnetic resonance data analysis.
CAS Number | 2140-79-6 |
Product Name | 2'-O-Methyladenosine |
IUPAC Name | (2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)-4-methoxyoxolan-3-ol |
Molecular Formula | C11H15N5O4 |
Molecular Weight | 281.27 g/mol |
InChI | InChI=1S/C11H15N5O4/c1-19-8-7(18)5(2-17)20-11(8)16-4-15-6-9(12)13-3-14-10(6)16/h3-5,7-8,11,17-18H,2H2,1H3,(H2,12,13,14)/t5-,7-,8-,11-/m1/s1 |
InChI Key | FPUGCISOLXNPPC-IOSLPCCCSA-N |
SMILES | COC1C(C(OC1N2C=NC3=C(N=CN=C32)N)CO)O |
Synonyms | 2'-O-methyladenosine, 2'-O-methyladenosine, (alpha-D-arabino)-isomer, 2'-O-methyladenosine, (beta-D-arabino)-isomer |
Canonical SMILES | COC1C(C(OC1N2C=NC3=C(N=CN=C32)N)CO)O |
Isomeric SMILES | CO[C@@H]1[C@@H]([C@H](O[C@H]1N2C=NC3=C(N=CN=C32)N)CO)O |
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