Phosphate → HCID 23276146, compound

HRID 2287198Notes

Reaction equation

HRID 2287198 reaction equation
[Na+].[OH:2][C:3]1[C:16]2[C:15](=[O:17])[CH:14]=[C:13]([C:18]([O-:20])=[O:19])[O:12][C:11]=2[C:10]([CH2:21][CH2:22][CH3:23])=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][CH2:8]2.P([O-])([O-])([O-])=[O:25].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.C(OP(O)(O)=O)[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O>>[OH:2][C:3]1[C:16]2[C:15](=[O:17])[CH:14]=[C:13]([C:18]([OH:20])=[O:19])[O:12][C:11]=2[C:10]([CH2:21][CH2:22][CH3:23])=[C:9]2[C:4]=1[CH2:5][CH:6]([OH:25])[CH2:7][CH2:8]2

Participants

5

Reactant 4

HCID 1061PhosphateHCID 439427Beta-D-Glucose 6-phosphateHCID 23668092HCID 23668092, compoundHCID 71717786[[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2S,3R,4S,5S)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate

Product 1

HCID 23276146HCID 23276146, compound

Procedure

A mixture of 5 parts 6,7,8,9-tetrahydro-5-hydroxy-4-oxo-10-propyl-4H-naphtho[2,3-b]pyran-2-carboxylic acid sodium salt, 4 parts of 25% w/v supernatant liver fraction, 10 parts of phosphate buffer pH 7.4, one part of nicotinamide adenine dinucleotide phosphate and one part of glucose-6-phosphate was incubated in a shaking incubator at 37° C. for 30 minutes. The reaction was stopped and protein was precipitated by the addition of 5 parts of 2 N hydrochloric acid. The reaction mixture was extracted three times with 100 parts of diethyl ether and after being dried over anhydrous sodium sulphate the extracts were evaporated to dryness at room temperature in a current of air. The 5,7-dihydroxy-6,7,8,9-tetrahydro-4-oxo-10-propyl-4H-naphtho[2,3-b]pyran-2-carboxylic acid and the other dihydroxy compounds identified in Example 1 were isolated by the preparative layer chromatography technique described in Example 1.

Workup

  1. customprotein was precipitated by the addition of 5 parts of 2 N hydrochloric acid
  2. extractionThe reaction mixture was extracted three times with 100 parts of diethyl ether
  3. dry with materialafter being dried over anhydrous sodium sulphate the extracts
  4. customwere evaporated to dryness at room temperature in a current of air
  5. customwere isolated by the preparative layer chromatography technique

Sources & evidence

ORD record
ord-86045fdefbd144d2ba3f85d4bf63eb2e
Source dataset
uspto-grants-1981_05
Patent number
US04269854

Reaction notes

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