| Identification | Back Directory | [Name]
2'-O-(2-Methoxyethyl)guanosine | [CAS]
473278-54-5 | [Synonyms]
2'-MOE-rG
2'-O-MOE-Gr
2'-O-MOE-rG
2'-O-Methoxyethyl-guanosine
2'-O-(2-Methoxyethyl)guanosine
Guanosine, 2'-O-(2-Methoxyethyl)-
2'-O-(2-Methoxyethyl)-guanosine, >97%
2-amino-9-((2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-(2-methoxyethoxy)tetrahydrofuran-2-yl)-1,9-dihydro-6H-purin-6-one | [EINECS(EC#)]
1308068-626-2 | [Molecular Formula]
C13H19N5O6 | [MDL Number]
MFCD02682962 | [MOL File]
473278-54-5.mol | [Molecular Weight]
341.32 |
| Chemical Properties | Back Directory | [Boiling point ]
715.0±70.0 °C(Predicted) | [density ]
1.81±0.1 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,2-8°C | [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 |
| Hazard Information | Back Directory | [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 |
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