2′-O-Methyladenosine, CAS:2140-79-6

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Catalog No: A10GD-5272

2140-79-6 , 2′-O-Methyladenosine,

CAS:2140-79-6

MFCD00056002

C11H15N5O4 /281.27

white to off-white powder.

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2′-O-Methyladenosine

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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Size

1 G, 100 MG, 5 G, Other

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