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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1919274Generated: November 1, 2026

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

https://huagongshe.com/reaction/1919274

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPyridoxal 5'-phosphateHCID 1051—
ReactantNadide (JAN/USAN/INN)HCID 5893—
ReactantSodium HydroxideHCID 14798—
Reactant1-(p-Methoxyphenyl)-2-propanoneHCID 31231—
ReactantD-AlanineHCID 71080—
Reactant(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 107526—
Product(+-)-p-MethoxyamphetamineHCID 31721—

Reaction Steps

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.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08168412B2
Source datasetuspto-grants-2012_05
ORD IDord-de809c94e52644a19f2bc432f30824a5
Source noteuspto-grants-2012_05