N2-(2-METHYLPROPANOYL)-GUANOSINE Chemical Properties

Melting point:

148 °C

Density 

1.82±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,2-8°C

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

9.16±0.20(Predicted)

color 

White to Off-White

InChIKey

OXTYJSXVUGJSGM-HTVVRFAVSA-N

SMILES

OC[C@H]1O[C@@H](N2C3=C(C(NC(=N3)NC(=O)C(C)C)=O)N=C2)[C@H](O)[C@@H]1O

CAS DataBase Reference

64350-24-9

Safety Information

HS Code 

29389090

N2-(2-METHYLPROPANOYL)-GUANOSINE Usage And Synthesis

Description

N2-Isobutyrylguanosine is a synthetic nucleoside analog. N-Isobutyrylguanosine can be used in the syntehsis of 2'-O-(o-nitrobenzyl)-3'-thioguanosine phosphoramidite which is then used to form oligonucleotides, substrates for probing the mechanism of RNA catalysis.

Chemical Properties

White solid

Uses

N-Isobutyrylguanosine is used in the syntehsis of 2''-O-(o-nitrobenzyl)-3''-thioguanosine phosphoramidite which is then used to form oligonucleotides, substrates for probing the mechanism of RNA catalysis.

Definition

ChEBI: N-Isobutyrylguanosine is a purine nucleoside.

Synthesis

GENERAL STEPS: To a solution of guanosine (1 g, 3.53 mmol) in pyridine (25 mL) was added trimethylsilyl chloride (TMSCl) (3.35 mL, 26.47 mmol). The reaction mixture was stirred at room temperature for 2 hours. Subsequently, the reaction system was cooled to 0°C and isobutyryl chloride was slowly added. After addition, the reaction solution was returned to room temperature and continued stirring. Upon completion of the reaction, water (10 mL) was slowly added at 0 °C, followed by additional water (10 mL) at 5 °C. After 5 min, ammonia (NH4OH) was added. after 15 min, water (50 mL) and dichloromethane (CH2Cl2) (20 mL) were added for extraction. The aqueous phase was separated and concentrated under reduced pressure, the resulting solid was recrystallized with hot water, filtered and the solvent was evaporated under reduced pressure to afford the target compound N-(9-(((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide (82% yield). The product was confirmed by 1H-NMR (200 MHz, DMSO-d6), ESI MS characterization.1H-NMR (200 MHz, DMSO-d6) δ: 1.10,1.13 (6H, s, (CH3)2CH), 2.75-2.76 (1H, m, CH), 3.56-3.59 (2H, m, H-5'), 3.88- 3.90 (1H, m, H-4'), 4.11-4.13 (1H, m, H-3'), 4.41-4.44 (1H, m, H-2'), 5.04 (1H, t, J=4.6 Hz, OH-5'), 5.45 (1H, d, J=3.8 Hz, OH-3'), 5.48 (1H, d, J=4.0 Hz, OH-2 '), 5.80 (1H, d, J=5.4Hz, H-1'), 8.26 (1H, s, H-8), 11.90 (1H, br s, NH-CO), 12.16 (1H, br s, NH-3).ESI MS: m/z 354.2Da [M+H]+, molecular formula C14H19N5O6, molecular weight 353.33.

References

[1] European Journal of Medicinal Chemistry, 2012, vol. 54, p. 202 - 209
[2] Bioorganic and medicinal chemistry, 2003, vol. 11, # 2, p. 235 - 249
[3] Patent: US2011/86813, 2011, A1. Location in patent: Page/Page column 30
[4] Nucleosides, Nucleotides and Nucleic Acids, 2004, vol. 23, # 1-2, p. 171 - 181
[5] Patent: EP1710249, 2006, A1. Location in patent: Page/Page column 17

N2-(2-METHYLPROPANOYL)-GUANOSINE(64350-24-9)Related Product Information

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