Hydrochloric Acid → Tetrahydrofolic acid

HRID 1530190Notes

Reaction equation

HRID 1530190 reaction equation
[OH-].[NH4+].Cl.O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.[C:16]([O-:47])(=[O:46])[CH2:17][CH2:18][C@H:19]([NH:23][C:24]([C:26]1[CH:45]=[CH:44][C:29]([NH:30][CH2:31][C:32]2[CH2:33][NH:34][C:35]3[N:36]=[C:37]([NH:39][C:40]([C:42]=3[N:43]=2)=[O:41])[NH2:38])=[CH:28][CH:27]=1)=[O:25])[C:20]([OH:22])=[O:21].C1C=[N+]([C@@H]2O[C@H](COP(OP(OC[C@H]3O[C@@H](N4C5N=CN=C(N)C=5N=C4)[C@H](OP(O)(O)=O)[C@@H]3O)(O)=O)(O)=O)[C@@H](O)[C@H]2O)C=C(C(N)=O)C=1>O>[C:16]([OH:47])(=[O:46])[CH2:17][CH2:18][C@H:19]([NH:23][C:24]([C:26]1[CH:27]=[CH:28][C:29]([NH:30][CH2:31][CH:32]2[NH:43][C:42]3[C:40](=[O:41])[NH:39][C:37]([NH2:38])=[N:36][C:35]=3[NH:34][CH2:33]2)=[CH:44][CH:45]=1)=[O:25])[C:20]([OH:22])=[O:21]

Participants

7

Reactant 5

HCID 313Hydrochloric Acid2×HCID 5886NADP nicotinamide-adenine-dinucleotide phosphateHCID 14923Ammonium Hydroxide2×HCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal3×HCID 136400727(4S)-4-[[4-[(2-amino-4-oxo-7,8-dihydro-3H-pteridin-6-yl)methylamino]benzoyl]amino]-5-hydroxy-5-oxopentanoate2×

Product 1

HCID 135444742Tetrahydrofolic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent4×

Procedure

In the second step, the recovered solid is suspended in water (100 mL) and concentrated ammonium hydroxide (7.2 mL) is added to dissolve the solid and attain a pH of 8.6. The pH of this solution is adjusted to 7.5 by the addition of 6N hydrochloric acid (9 mL). To this solution is added glucose dehydrogenase (20 mg), dihydrofolate reductase (7 mg), NADP (280 mg), glucose (6 g) and water (40 mL). This solution is allowed to stir under N2 for 1 hour. After this time glucose dehydrogenase (16 mg), dihydrofolate reductase (8 mg) and water (20 mL) is added. This solution is allowed to stir for 3.5 hours. The pH of this solution is maintained at 7.5 by the intermittent addition of concentrated ammonium hydroxide. Concentrated hydrochloric acid (9.5 mL) is added to the solution in order to attain a pH of 2.9. The precipitate formed is isolated by centrifugation or other suitable means. The solid is suspended in water (100 mL) and isolated by vacuum filtration. The solid is dried in vacuo at 40° C. overnight to give 5.037 grams of crude tetrahydrofolic acid.

Workup

  1. dissolutionto dissolve the solid
  2. stirringto stir for 3.5 hours
  3. customThe precipitate formed
  4. customis isolated by centrifugation or other suitable means
  5. customisolated by vacuum filtration
  6. customThe solid is dried in vacuo at 40° C. overnight

Sources & evidence

ORD record
ord-3bc7bdf570be4648bb59668b68dff328
Source dataset
uspto-grants-2015_07
Patent number
US09090925B2

Reaction notes

Loading…