2'-O-Methylguanosine | CAS#2140-71-8 | Nucleosides

2'-O-Methylguanosine
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 122496

CAS#: 2140-71-8

Description: 2'-O-methylguanosine is guanosine with the hydrogen on the hydroxyl at position C-2' substituted with a methyl group. It has a role as a metabolite.

Chemical Structure

2'-O-Methylguanosine

CAS# 2140-71-8

Instruction

Theoretical Analysis

MedKoo Cat#: 122496
Name: 2'-O-Methylguanosine
CAS#: 2140-71-8
Chemical Formula: C11H15N5O5
Exact Mass: 297.11
Molecular Weight: 297.270
Elemental Analysis: C, 44.44; H, 5.09; N, 23.56; O, 26.91

Price and Availability

Size	Price	Availability
1g	USD 450	2 Weeks
5g	USD 950	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: 2'-O-Methylguanosine; 2140-71-8; 2'-O-Methyl guanosine; 2'-O-METHYL-GUANOSINE; Guanosine, 2'-O-methyl-

IUPAC/Chemical Name: 2-amino-9-((2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxytetrahydrofuran-2-yl)-3,9-dihydro-6H-purin-6-one

InChi Key: OVYNGSFVYRPRCG-KQYNXXCUSA-N

InChi Code: InChI=1S/C11H15N5O5/c1-20-7-6(18)4(2-17)21-10(7)16-3-13-5-8(16)14-11(12)15-9(5)19/h3-4,6-7,10,17-18H,2H2,1H3,(H3,12,14,15,19)/t4-,6-,7-,10-/m1/s1

SMILES Code: OC[C@@H]1[C@H]([C@H]([C@H](N2C=NC3=C2NC(N)=NC3=O)O1)OC)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

More Info:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 297.27 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.

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

Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Chow S, Wen K, Sanghvi YS, Theodorakis EA. Novel synthesis of
2'-O-methylguanosine. Bioorg Med Chem Lett. 2003 May 19;13(10):1631-4. doi:
10.1016/s0960-894x(03)00291-9. PMID: 12729629.

2: Roovers M, Labar G, Wolff P, Feller A, Van Elder D, Soin R, Gueydan C, Kruys
V, Droogmans L. The Bacillus subtilis open reading frame ysgA
encodes the SPOUT methyltransferase RlmP forming 2'-O-methylguanosine at
position 2553 in the A-loop of 23S rRNA. RNA. 2022 Sep;28(9):1185-1196. doi:
10.1261/rna.079131.122. Epub 2022 Jun 16. PMID: 35710145; PMCID: PMC9380741.

3: 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.

4: 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.

5: Kumagai I, Watanabe K, Oshima T. Thermally induced biosynthesis of
2'-O-methylguanosine in tRNA from an extreme thermophile, Thermus thermophilus
HB27. Proc Natl Acad Sci U S A. 1980 Apr;77(4):1922-6. doi:
10.1073/pnas.77.4.1922. PMID: 6990416; PMCID: PMC348621.

6: Inoue H, Hayase Y, Imura A, Iwai S, Miura K, Ohtsuka E. Synthesis and
hybridization studies on two complementary nona(2'-O-methyl)ribonucleotides.
Nucleic Acids Res. 1987 Aug 11;15(15):6131-48. doi: 10.1093/nar/15.15.6131.
PMID: 3627981; PMCID: PMC306073.

7: Pasternak A, Kierzek E, Pasternak K, Fratczak A, Turner DH, Kierzek R. The
thermodynamics of 3'-terminal pyrene and guanosine for the design of
isoenergetic 2'-O-methyl-RNA-LNA chimeric oligonucleotide probes of RNA
structure. Biochemistry. 2008 Feb 5;47(5):1249-58. doi: 10.1021/bi701758z. Epub
2008 Jan 5. PMID: 18177022.

8: He CC, Hamlow LA, Devereaux ZJ, Zhu Y, Nei YW, Fan L, McNary CP, Maitre P,
Steinmetz V, Schindler B, Compagnon I, Armentrout PB, Rodgers MT. Structural and
Energetic Effects of O2'-Ribose Methylation of Protonated Purine Nucleosides. J
Phys Chem B. 2018 Oct 4;122(39):9147-9160. doi: 10.1021/acs.jpcb.8b07687. Epub
2018 Sep 25. PMID: 30203656.

9: Vold BS. Preparation and specificity of antibodies directed toward the ribose
methylated nucleotide, 2'-O-methylguanosine 5'-monophosphate. Biochim Biophys
Acta. 1981 Sep 28;655(2):265-7. doi: 10.1016/0005-2787(81)90017-4. PMID:
6269628.

10: Vold BS, Keith DE Jr, Slavik M. Urine levels of N-[9-(beta-D-
ribofuranosyl)purin-6-ylcarbamoyl]-L-threonine, N6-(delta
2-isopentenyl)adenosine, and 2'-O-methylguanosine as determined by
radioimmunoassay for normal subjects and cancer patients. Cancer Res. 1982
Dec;42(12):5265-9. PMID: 7139629.

11: Stäheli P, Agris PF, Niederberger P, Gehrke CW, Hütter R. Accumulation of
2'-O-methylguanosine deficient tRNATrp in tryptophan limited Saccharomyces
cerevisiae. J Gen Microbiol. 1982 Nov;128(11):2591-600. doi:
10.1099/00221287-128-11-2591. PMID: 6759616.

12: Zhou L, Hayden A, Chandrasekaran AR, Vilcapoma J, Cavaliere C, Dey P, Mao S,
Sheng J, Dey BK, Rangan P, Halvorsen K. Sequence-selective purification of
biological RNAs using DNA nanoswitches. Cell Rep Methods. 2021 Dec
20;1(8):100126. doi: 10.1016/j.crmeth.2021.100126. Epub 2021 Dec 13. PMID:
35072148; PMCID: PMC8782281.

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