Pyridoxal 5'-phosphate → (+-)-p-Methoxyamphetamine

HRID 1919274Notes

Reaction equation

HRID 1919274 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](=O)[CH3:11])=[CH:5][CH:4]=1.O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.C1C=[N+:29]([C@@H]2O[C@H](COP(OP(OC[C@H]3O[C@@H](N4C5N=CN=C(N)C=5N=C4)[C@H](O)[C@@H]3O)(O)=O)(O)=O)[C@@H](O)[C@H]2O)C=C(C(N)=O)C=1.N[C@@H](C(O)=O)C.CC1N=CC(COP(O)(O)=O)=C(C=O)C=1O.[OH-].[Na+]>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH:10]([NH2:29])[CH3:11])=[CH:5][CH:4]=1

Participants

7

Reactant 6

HCID 1051Pyridoxal 5'-phosphateHCID 5893Nadide (JAN/USAN/INN)HCID 14798Sodium HydroxideHCID 312311-(p-Methoxyphenyl)-2-propanoneHCID 71080D-AlanineHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

Product 1

HCID 31721(+-)-p-Methoxyamphetamine

Procedure

To a flask containing 1.5 g of a substrate 1-(4-methoxyphenyl)-2-propanone, 4.94 g of D-glucose, 6.1 mg of NAD+, 4.88 g of D-alanine, and 4.0 mg of pyridoxal phosphate, 30 ml of a culture fluid of the E. coli HB101 (pNTASPAG), obtained in Example 11, which expresses TAS, PALDH, and GDH were added. The resultant product was stirred at 30° C. while being adjusted to a pH of 6.8 by drippage of 5 N aqueous solution of sodium hydroxide. During the reaction, the reaction liquid was sampled. From the sample, 1-(4-methoxyphenyl)-2-aminopropane was extracted by the addition of ethyl acetate after basifying the sample with 6 N aqueous solution of sodium hydroxide. The amount of 1-(4-methoxyphenyl)-2-aminopropane produced was measured by analyzing 1-(4-methoxyphenyl)-2-aminopropane under the following HPLC conditions. Further, by the law of the art, 1-(4-methoxyphenyl)-2-aminopropane thus obtained was acted on by 3,5-dinitrobenzyl chloride to form a dinitrobenzyl derivative. After that, the dinitrobenzyl derivative was analyzed under the following HPLC conditions, whereby the optical purity thereof was measured.

Workup

  1. custom(pNTASPAG), obtained in Example 11, which
  2. additionwere added
  3. customDuring the reaction
  4. customthe reaction liquid
  5. aliquotwas sampled
  6. extractionFrom the sample, 1-(4-methoxyphenyl)-2-aminopropane was extracted by the addition of ethyl acetate

Sources & evidence

ORD record
ord-de809c94e52644a19f2bc432f30824a5
Source dataset
uspto-grants-2012_05
Patent number
US08168412B2

Reaction notes

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