Dimethyl Sulfoxide → 2'-O-Octadecylguanosine

HRID 363243

Reaktionsgleichung

Reaktionsgleichung von HRID 363243
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[O:35][C@H:34]([CH2:36][OH:37])[C@@H:32]([OH:33])[C@H:12]2[O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[C:4](N)[N:3]=1.CS(C)=[O:41].[C@@H]1(N2C3N=CN=C(N)C=3N=C2)O[C@H](CO)[C@@H](O)[C@H]1O>P([O-])([O-])([O-])=O.[Na+].[Na+].[Na+]>[CH2:14]([O:13][C@@H:12]1[C@H:32]([OH:33])[C@@H:34]([CH2:36][OH:37])[O:35][C@H:11]1[N:8]1[C:9]2[N:10]=[C:2]([NH2:1])[NH:3][C:4](=[O:41])[C:5]=2[N:6]=[CH:7]1)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

Komponenten

5

Edukt 3

HCID 679Dimethyl SulfoxideHCID 60961Adenosine2×HCID 117311872,6-Diamino-9-(2-O-octadecyl-beta-D-ribofuranosyl)purine

Produkt 1

HCID 1355097442'-O-Octadecylguanosine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24243Trisodium PhosphateLösungsmittel

Versuchsvorschrift

2,6-Diamino-9-(2-O-octadecyl-β-D-ribofuranosyl) purine (10 g) in 0.1M sodium phosphate buffer (50 ml, pH 7.4), 0.1M tris buffer (1000 ml, pH 7.4) and DMSO (1000 ml) was treated with adenosine deaminase (1.5 g) at RT. At day 3, day 5 and day 7 an additional aliquot (500 mg, 880 mg and 200 mg, respectively) of adenosine deaminase was added. The reaction was stirred for a total of 9 day and purification by silica gel chromatography yielded the product (2 g). An analytical sample was recrystallized from MeOH. 1H NMR (DMSO-d6) δ 0.84 (t, 3, CH3), 1.22 (s, 32, O--CH2 --CH2 --(CH2)16), 5.07 (m, 2,3'-OH and 5'-OH), 5.78 (d, 1,1'H), 6.43 (s, 2, NH2), 7.97 (s, 1,8 H) and 10.64 (s, 1, NH2). Anal. Calcd. for C28H49N5O5 : C, 62.80; H, 9.16; N, 12.95. Found: C, 62.54; H, 9.18; N, 12.95.

Aufarbeitung

  1. waitAt day 3, day 5 and day 7 an additional aliquot (500 mg, 880 mg and 200 mg

Quellen und Nachweise

ORD-Eintrag
ord-0323960fb272486b8408fdf5e76ca269
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05872232

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