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

pka

13.20±0.70(Predicted)

form 

Solid

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(473278-54-5)Related Product Information

• Ethylhexyl Triazone
• 2'-O-Methylcytidine
• DMT-2μ-O-Me-rG(ib) amidite
• 2’-O-Methyl-rA(N-Bz)phosphoramidite
• DMT-2′Fluoro-dU Phosphoramidite
• 2'-O-MOE-A(Bz)-3'-phosphoramidite
• 2'-O-(2-Methoxyethyl)-5-methyluridine
• N-blocked-5'-O-DMT-2'-O-Me CED cytosine phosphoramidite
• N4-Benzoyl-5'-O-DMT-2'-O-methyl-5-methylcytidine 3'-CE phosphoramidite
• Dmt-2'-f-dc(ac) amidite
• 2'-O-Methyladenosine
• 2'-O-(2-Methoxyethyl)cytidine
• 2'-O-Methylguanosine
• 2'-O-(2-Methoxyethyl)uridine
• DMT-2'-O-MOE-rU Phosphoramidite
• 2'-O-MOE-ADENOSINE
• 2'-OMe-ibu-G Phosphoramidite