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| | 2'-O-(2-Methoxyethyl)guanosine Basic information |
| | 2'-O-(2-Methoxyethyl)guanosine Chemical Properties |
| Boiling point | 715.0±70.0 °C(Predicted) | | density | 1.81±0.1 g/cm3(Predicted) | | storage temp. | 2-8°C(protect from light) | | solubility | Acetonitrile: Slightly Soluble: 0.1-1 mg/ml
DMSO: Sparingly Soluble: 1-10 mg/ml
Water: Slightly Soluble: 0.1-1 mg/ml | | form | Solid | | pka | 13.20±0.70(Predicted) | | color | White to off-white | | InChI | 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 | | InChIKey | DLLBJSLIKOKFHE-WOUKDFQISA-N | | SMILES | OC[C@H]1O[C@@H](N2C3=C(C(NC(=N3)N)=O)N=C2)[C@H](OCCOC)[C@@H]1O |
| | 2'-O-(2-Methoxyethyl)guanosine Usage And Synthesis |
| Description | 2'-O-(2-Methoxyethyl)-guanosine is a guanosine derivative isolated from the reaction of 2-aminoadenosine with methylsulfonyl chloride. 2'-O-(2-Methoxyethyl)-guanosine can be used as a building block for cross-linking oligonucleotides. | | Uses | A guanosine derivative as building blocks for cross-linking oligonucleotides. | | Definition |
2'-O-(2-Methoxyethyl)guanosine, a 2′-O-methoxyethyl-modified nucleoside, can be produced by enzymatic conversion (adenosine deaminase) from 2′-O-(2-methoxyethyl)-2,6-diaminopurine riboside.
| | Synthesis | Compound 7 (50 mg, 0.086 mmol) was used as a starting material, which was dissolved in a mixed solvent of THF and water, and TBAF (1 M solution of THF, 0.009 mL, 0.009 mmol) was added at 25 °C. The reaction mixture was warmed up to 35 °C with continuous stirring for 5 hours. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue was purified by filtration through a short silica gel column using a dichloromethane solution of 10% methanol as eluent to afford the target product 2'-O-MOE G (compound 8) (28 mg, 0.082 mmol, 97% yield). The 1H NMR (400 MHz, DMSO) data of compound 8 were as follows: δ 10.68 (s, 1H), 7.95 (s, 1H), 6.50 (s, 2H), 5.78 (d, J = 6.0 Hz, 1H), 5.08 (d, J = 5.2 Hz, 2H), 4.33 (d, J = 6.0 Hz, 1H), 4.23 (d, J = 3.2 Hz, 1H), 3.88 (d, J = 3.2 Hz, 1H), 3.65 (m, 3H), 3.52-3.57 (m, 2H), 3.35 (s, 3H), 3.38-3.40 (m, 1H). | | References | [1] Nucleosides, nucleotides and nucleic acids, 2003, vol. 22, # 5-8, p. 583 - 587
[2] The Journal of organic chemistry, 2002, vol. 67, # 22, p. 7887 - 7889
[3] Patent: US2003/225262, 2003, A1. Location in patent: Page column 34-35
[4] AMER F SALEH. 2’-O-(2-Methoxyethyl) Nucleosides Are Not Phosphorylated or Incorporated Into the Genome of Human Lymphoblastoid TK6 Cells.[J]. Toxicological Sciences, 2018: 70-78. DOI: 10.1093/toxsci/kfy005 |
| | 2'-O-(2-Methoxyethyl)guanosine Preparation Products And Raw materials |
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