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

MedKoo Cat#: 122496 | Name: 2'-O-Methylguanosine

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Description:

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

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

Theoretical Analysis

MedKoo Cat#: 122496

Name: 2'-O-Methylguanosine

CAS#: 2140-71-8

Chemical Formula: C11H15N5O5

Exact Mass: 297.1073

Molecular Weight: 297.27

Elemental Analysis: C, 44.44; H, 5.09; N, 23.56; O, 26.91

Price and Availability

Size	Price	Availability
1g	USD 250.00	2 Weeks
2g	USD 400.00	2 Weeks
5g	USD 850.00	2 Weeks

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Related CAS #

No Data

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

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

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.