MedKoo Cat#: 122490 | Name: 2'-O-Methyladenosine
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

2'-O-Methyladenosine has a role as a fungal metabolite.

Chemical Structure

2'-O-Methyladenosine
2'-O-Methyladenosine
CAS#2140-79-6

Theoretical Analysis

MedKoo Cat#: 122490

Name: 2'-O-Methyladenosine

CAS#: 2140-79-6

Chemical Formula: C11H15N5O4

Exact Mass: 281.1124

Molecular Weight: 281.27

Elemental Analysis: C, 46.97; H, 5.38; N, 24.90; O, 22.75

Price and Availability

Size Price Availability Quantity
1g USD 350.00 2 Weeks
2g USD 550.00 2 Weeks
5g USD 950.00 2 Weeks
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Related CAS #
No Data
Synonym
2'-O-Methyladenosine; 2140-79-6; Adenosine, 2'-O-methyl-; cordysinin B
IUPAC/Chemical Name
(2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)-4-methoxytetrahydrofuran-3-ol
InChi Key
FPUGCISOLXNPPC-IOSLPCCCSA-N
InChi Code
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
SMILES Code
O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC3=C(N)N=CN=C23)[C@@H]1OC
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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 281.27 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.

Recalculate based on batch purity %
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: Oerum S, Meynier V, Catala M, Tisné C. A comprehensive review of m6A/m6Am RNA methyltransferase structures. Nucleic Acids Res. 2021 Jul 21;49(13):7239-7255. doi: 10.1093/nar/gkab378. PMID: 34023900; PMCID: PMC8287941. 2: He Q, Yang L, Gao K, Ding P, Chen Q, Xiong J, Yang W, Song Y, Wang L, Wang Y, Ling L, Wu W, Yan J, Zou P, Chen Y, Zhai R. Correction: FTSJ1 regulates tRNA 2'-O-methyladenosine modification and suppresses the malignancy of NSCLC via inhibiting DRAM1 expression. Cell Death Dis. 2020 Jun 3;11(6):418. doi: 10.1038/s41419-020-2623-9. Erratum for: Cell Death Dis. 2020 May 11;11(5):348. PMID: 32488007; PMCID: PMC7266812. 3: He Q, Yang L, Gao K, Ding P, Chen Q, Xiong J, Yang W, Song Y, Wang L, Wang Y, Ling L, Wu W, Yan J, Zou P, Chen Y, Zhai R. FTSJ1 regulates tRNA 2'-O-methyladenosine modification and suppresses the malignancy of NSCLC via inhibiting DRAM1 expression. Cell Death Dis. 2020 May 11;11(5):348. doi: 10.1038/s41419-020-2525-x. Erratum in: Cell Death Dis. 2020 Jun 3;11(6):418. PMID: 32393790; PMCID: PMC7214438. 4: Li P, Liu Y, Song R, Zhao L, Yang J, Lu F, Cao X. RNA 2'-O-Methyltransferase Fibrillarin Facilitates Virus Entry Into Macrophages Through Inhibiting Type I Interferon Response. Front Immunol. 2022 Apr 7;13:793582. doi: 10.3389/fimmu.2022.793582. PMID: 35464456; PMCID: PMC9021640. 5: Wang Y, Li D, Gao J, Li X, Zhang R, Jin X, Hu Z, Zheng B, Persson S, Chen P. The 2'-O-methyladenosine nucleoside modification gene OsTRM13 positively regulates salt stress tolerance in rice. J Exp Bot. 2017 Mar 1;68(7):1479-1491. doi: 10.1093/jxb/erx061. PMID: 28369540; PMCID: PMC5444449. 6: Dong H, Chang DC, Hua MH, Lim SP, Chionh YH, Hia F, Lee YH, Kukkaro P, Lok SM, Dedon PC, Shi PY. 2'-O methylation of internal adenosine by flavivirus NS5 methyltransferase. PLoS Pathog. 2012;8(4):e1002642. doi: 10.1371/journal.ppat.1002642. Epub 2012 Apr 5. PMID: 22496660; PMCID: PMC3320599. 7: Qu X, Zhang Y, Sang X, Ren D, Zhao H, Wong STC. Methyladenosine Modification in RNAs: From Regulatory Roles to Therapeutic Implications in Cancer. Cancers (Basel). 2022 Jun 29;14(13):3195. doi: 10.3390/cancers14133195. PMID: 35804965; PMCID: PMC9264946. 8: BROOM AD, ROBINS RK. THE DIRECT PREPARATION OF 2'-O-METHYLADENOSINE FROM ADENOSINE. J Am Chem Soc. 1965 Mar 5;87:1145-6. doi: 10.1021/ja01083a045. PMID: 14284632. 9: Keith JM, Ensinger MJ, Moss B. HeLa cell RNA (2'-O-methyladenosine-N6-)-methyltransferase specific for the capped 5'-end of messenger RNA. J Biol Chem. 1978 Jul 25;253(14):5033-9. PMID: 670176. 10: Mitsukawa Y, Hibi M, Matsutani N, Horinouchi N, Takahashi S, Ogawa J. Enzymatic synthesis of 2'-O-methylribonucleosides with a nucleoside hydrolase family enzyme from Lactobacillus buchneri LBK78. J Biosci Bioeng. 2017 Jun;123(6):659-664. doi: 10.1016/j.jbiosc.2017.01.005. Epub 2017 Feb 12. PMID: 28202305. 11: Kajino R, Sakamoto S, Ueno Y. Synthesis, gene silencing activity, thermal stability, and serum stability of siRNA containing four (S)-5'-C-aminopropyl-2'-O-methylnucleosides (A, adenosine; U, uridine; G, guanosine; and C, cytidine). RSC Adv. 2022 Apr 12;12(18):11454-11476. doi: 10.1039/d2ra00705c. PMID: 35425057; PMCID: PMC9002251. 12: Yano J, Kan LS, Ts'o PO. A simple method of the preparation of 2'-O-methyladenosine. Methylation of adenosine with methyl iodide in anhydrous alkaline medium. Biochim Biophys Acta. 1980 Apr 17;629(1):178-83. doi: 10.1016/0304-4165(80)90276-7. PMID: 7370305. 13: Gerard GF, Rottman F, Boezi JA. 2'-O-methyladenosine 5'-triphosphate. A substrate for deoxyribonucleic acid dependent ribonucleic acid polymerase of Pseudomonas putida. Biochemistry. 1971 May 25;10(11):1974-81. doi: 10.1021/bi00787a003. PMID: 4935104. 14: al-Arif A, Sporn MB. 2'-O-methylation of adenosine, guanosine, uridine, and cytidine in RNA of isolated rat liver nuclei. Proc Natl Acad Sci U S A. 1972 Jul;69(7):1716-9. doi: 10.1073/pnas.69.7.1716. PMID: 4340155; PMCID: PMC426785.