PeptideDB

2′-O-(2-Methoxyethyl)guanosine (2′-O-MOE-rG) 473278-54-5

2′-O-(2-Methoxyethyl)guanosine (2′-O-MOE-rG) 473278-54-5

CAS No.: 473278-54-5

2'-O-(2-Methoxyethyl)guanosine (2'-O-MOE-rG) is a 2'-O-methoxyethyl modified nucleoside, which can be synthesized from 2
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2'-O-(2-Methoxyethyl)guanosine (2'-O-MOE-rG) is a 2'-O-methoxyethyl modified nucleoside, which can be synthesized from 2'-O-(2-methoxyethyl)- 2,6-diaminopurine riboside is generated by enzymatic conversion (adenosine deaminase). 2′-O-(2-Methoxyethyl)guanosine is not efficiently phosphorylated by cytosolic nucleoside kinases and cannot be incorporated into cellular DNA or RNA.

Physicochemical Properties


Molecular Formula C13H19N5O6
Molecular Weight 341.32
Exact Mass 341.134
CAS # 473278-54-5
PubChem CID 135544588
Appearance White to off-white solid powder
Density 1.811g/cm3
Index of Refraction 1.745
LogP -1.5
Hydrogen Bond Donor Count 4
Hydrogen Bond Acceptor Count 8
Rotatable Bond Count 6
Heavy Atom Count 24
Complexity 505
Defined Atom Stereocenter Count 4
SMILES

COCCO[C@@H]1[C@@H]([C@H](O[C@H]1N2C=NC3=C2N=C(NC3=O)N)CO)O

InChi Key DLLBJSLIKOKFHE-WOUKDFQISA-N
InChi Code

InChI=1S/C13H19N5O6/c1-22-2-3-23-9-8(20)6(4-19)24-12(9)18-5-15-7-10(18)16-13(14)17-11(7)21/h5-6,8-9,12,19-20H,2-4H2,1H3,(H3,14,16,17,21)/t6-,8-,9-,12-/m1/s1
Chemical Name

2-amino-9-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-(2-methoxyethoxy)oxolan-2-yl]-1H-purin-6-one
HS Tariff Code 2934.99.9001
Storage

Powder-20°C 3 years

4°C 2 years

In solvent -80°C 6 months

-20°C 1 month

Note: This product requires protection from light (avoid light exposure) during transportation and storage.
Shipping Condition Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity


References

[1]. An Improved Process for the Manufacture of 5′-O-(4,4′-Dimethoxytrityl)-N2-isobutyryl-2′-O-(2-methoxyethyl)guanosine. Org. Process Res. Dev. 2020, 24, 11, 2583-2590.

[2]. 2'-O-(2-Methoxyethyl) Nucleosides Are Not Phosphorylated or Incorporated Into the Genome of Human Lymphoblastoid TK6 Cells. Toxicol Sci. 2018 May 1;163(1):70-78.


Solubility Data


Solubility (In Vitro) DMSO : 250 mg/mL (732.45 mM)
Solubility (In Vivo) Solubility in Formulation 1: ≥ 2.08 mg/mL (6.09 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.08 mg/mL (6.09 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

Solubility in Formulation 3: ≥ 2.08 mg/mL (6.09 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.9298 mL 14.6490 mL 29.2980 mL
5 mM 0.5860 mL 2.9298 mL 5.8596 mL
10 mM 0.2930 mL 1.4649 mL 2.9298 mL
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.