2-(DIMETHYLAMINO)GUANOSINE Chemical Properties

Melting point:

249-251°C

Density 

1.83±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,2-8°C

solubility 

Aqueous Base (Sparingly), DMSO (Slightly), Methanol (Slightly), Water (Slightly,

form 

Solid

pka

9.63±0.20(Predicted)

color 

White to Off-White

PH

2.5；9.7

λmax

265 (pH 1)；260 (pH 7)；263 (pH 13)

InChI

InChI=1S/C12H17N5O5/c1-16(2)12-14-9-6(10(21)15-12)13-4-17(9)11-8(20)7(19)5(3-18)22-11/h4-5,7-8,11,18-20H,3H2,1-2H3,(H,14,15,21)/t5-,7-,8-,11-/m1/s1

InChIKey

RSPURTUNRHNVGF-IOSLPCCCSA-N

SMILES

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

Safety Information

WGK Germany 

3

HS Code 

29389090

MSDS

• Language:English Provider:SigmaAldrich

2-(DIMETHYLAMINO)GUANOSINE Usage And Synthesis

Description

N,N-Dimethylguanosine is a purine nucleoside that is found in human serum and belongs to the group of purines and has been shown to be involved in energy metabolism. N2,N2-Dimethylguanosine has been shown to be present at high levels in patients with autoimmune diseases such as rheumatoid arthritis.

Chemical Properties

White Solid

Uses

2-(Dimethylamino)guanosine (cas# 2140-67-2) is a compound useful in organic synthesis.

Definition

ChEBI: A guanosine where the hydrogens of the amine group at C-2 are substituted by methyl groups.

Synthesis

Compound 1 (CAS: 73196-87-9, 1.5 g, 3.4 mmol) was dissolved in pyridine (2 mL) followed by addition of ammonia. The reaction mixture was stirred at room temperature for 3 h. The progress of the reaction was monitored by thin layer chromatography (TLC) until it showed complete deprotection. After completion of the reaction, the solvent was evaporated to dryness under reduced pressure. The crude product was purified by recrystallization from water to afford the target product 9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-(dimethylamino)-1,9-dihydro-6H-purin-6-one in a yield of 0.68 g and 65%. The structure of the product was confirmed by 1H NMR, 13C NMR and mass spectrometry (ES-TOF).1H NMR (DMSO-d6) δ: 3.06 (6H, s, NMe2), 3.48-3.63 (2H, m, 5'-CH2), 3.86 (1H, q, J = 4 Hz, H4'), 4.11 (1H, q, J = 4 Hz, H3' ), 4.50 (1H, q, J = 4 Hz, H2'), 4.91 (1H, t, J = 5.4 Hz, OH5'), 5.15 (1H, d, J = 4.8 Hz, OH3'), 5.38 (1H, d, J = 6.1 Hz, OH2'), 5.71 (1H, d, J = 5.8 Hz, H1'), 5.92 (1H, s, H8 ), 10.69 (1H, bs, NH); 13C NMR δ: 38.1 (NMe2), 61.8 (C5'), 70.7 (C3'), 73.7 (C2'), 85.4 (C4'), 87.0 (C1'), 100.0, 116.4, 136.8 (C8), 151.1, 153.3, 157.7; MS ( ES-TOF) m/z: calculated value 312.13, measured value 312.54.

References

[1] Journal of Organic Chemistry, 1991, vol. 56, # 3, p. 1224 - 1227
[2] Journal of Organic Chemistry, 1996, vol. 61, # 13, p. 4412 - 4422
[3] Patent: US9067964, 2015, B2. Location in patent: Page/Page column 15

2-(DIMETHYLAMINO)GUANOSINE(2140-67-2)Related Product Information

• N,N-Dimethylacetamide
• 7,8-Dihydro-7-methylguanosine
• N,N-Dimethylaniline
• 2-(DIMETHYLAMINO)GUANOSINE
• N2-METHYL-2'-DEOXYGUANOSINE
• Guanosine
• 2',3',5'-TRI-O-ACETYL-2N,2N-DIMETHYL-GUANOSINE
• N2-METHYLGUANOSINE