Dimethyl Sulfate → HCID 178465533, compound

HRID 986078

Reaction equation

HRID 986078 reaction equation
[P:1]([O:13][CH2:14][C@H:15]1[O:19][C@@H:18]([N:20]2[C:30]3[N:29]=[C:27]([NH2:28])[NH:26][C:24](=[O:25])[C:23]=3[N:22]=[CH:21]2)[C@H:17]([OH:31])[C@@H:16]1[OH:32])([O:4][P:5]([O:8][P:9]([OH:12])([OH:11])=[O:10])([OH:7])=[O:6])(=[O:3])[OH:2].S(OC)(O[CH3:37])(=O)=O>>[CH3:37][N:22]1[C:23]2[C:24]([N:26]=[C:27]([NH2:28])[NH:29][C:30]=2[N+:20]([C@@H:18]2[O:19][C@H:15]([CH2:14][O:13][P:1]([O:4][P:5]([O:8][P:9]([OH:11])([OH:12])=[O:10])([OH:7])=[O:6])([OH:2])=[O:3])[C@@H:16]([OH:32])[C@H:17]2[OH:31])=[CH:21]1)=[O:25].[CH2:30]([NH+:20]([CH2:18][CH3:17])[CH2:21][CH3:37])[CH3:23]

Participants

3

Reactant 2

HCID 6497Dimethyl SulfateHCID 135398633Guanosine Triphosphate

Product 1

HCID 178465533HCID 178465533, compound

Procedure

Guanosine triphosphate (GTP) (300 mg, 0.5 mmol) was methylated using dimethyl sulfate according to the procedure of Hendler et al. ((1970) Biochemistry 9, 414) with modification. The reaction mixture was neutralized and the product purified on a DEAE Sephadex A-25 (Sephadex is a registered trademark of Pharmacia Fine Chemicals, Inc.) column (3×50 cm). The column was washed with water and then eluted with a linear gradient of 0 to 0.8M triethylammonium bicarbonate (TEAB), pH 7.8 (2 l total volume). Twenty-milliliter fractions were collected and assayed spectrophometrically at 260 nm. m7GTP eluted at approximately 0.4M, and the peak was pooled and repeatedly evaporated to dryness from water vacuo. m7GTP-triethylammonium salt was obtained as a white solid (0.25 mmol, 50% yield).

Workup

  1. customthe product purified on a DEAE Sephadex A-25 (Sephadex
  2. washThe column was washed with water
  3. washeluted with a linear gradient of 0 to 0.8M triethylammonium bicarbonate (TEAB), pH 7.8 (2 l total volume)
  4. customTwenty-milliliter fractions were collected
  5. washm7GTP eluted at approximately 0.4M
  6. customrepeatedly evaporated to dryness from water vacuo

Sources & evidence

ORD record
ord-0bbd8c4c618047118d9ee8b27e01bd24
Source dataset
uspto-grants-1987_12
Patent number
US04710566

Linked notes

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