Acetic Acid → O-acetyl-ADP-ribose

HRID 2207858Notes

Reaction equation

HRID 2207858 reaction equation
[C:1]([O-:4])([O-])=[O:2].[Na+].[Na+].[C:7]([OH:10])(=[O:9])[CH3:8].[CH:11]1[N:12]=[C:13]([NH2:54])[C:14]2[N:19]=[CH:18][N:17]([C@@H:20]3[O:24][C@H:23]([CH2:25][O:26][P:27]([O:30][P:31]([O:34][CH2:35][C@H:36]4O[C@@H](N5C=C(C(N)=O)CC=C5)[C@H:38](O)[C@@H:37]4[OH:51])([OH:33])=[O:32])([OH:29])=[O:28])[C@@H:22]([OH:52])[C@H:21]3[OH:53])[C:15]=2[N:16]=1>CC#N>[CH3:8][C:7]([O:10][C@H:38]1[CH:1]([OH:4])[O:2][C@H:36]([CH2:35][O:34][P:31]([O:30][P:27]([O:26][CH2:25][C@H:23]2[O:24][C@@H:20]([N:17]3[C:15]4[N:16]=[CH:11][N:12]=[C:13]([NH2:54])[C:14]=4[N:19]=[CH:18]3)[C@H:21]([OH:53])[C@@H:22]2[OH:52])([OH:29])=[O:28])([OH:33])=[O:32])[C@H:37]1[OH:51])=[O:9]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10340Sodium Carbonate2×HCID 439153Nadh

Product 1

HCID 72193709O-acetyl-ADP-ribose

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

To 80 mg of Na2CO3 was added 2 mL of glacial acetic acid. The mixture was stirred at 85° C. until all the Na2CO3 reacted. 250 mg of NAD was added and the mixture was stirred at 85° C. for 15 min, cooled to below 75° C. and diluted with 20 mL of CH3CN. The precipitate was filtered, suspended in 5 mL of CH3CN, and filtered again to give crude OAADPR.

Workup

  1. customreacted
  2. temperaturecooled to below 75° C.
  3. filtrationThe precipitate was filtered
  4. filtrationfiltered again

Sources & evidence

ORD record
ord-5d20857faddf48df8c28ec97b8c3ece1
Source dataset
uspto-grants-2016_06
Patent number
US09376461B2

Reaction notes

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