酶促化学合成 5-甲基色胺：一种具有潜在致幻活性的色胺。
Chemoenzymatic Synthesis of 5-Methylpsilocybin: A Tryptamine with Potential Psychedelic Activity.
机构信息
Department Pharmaceutical Microbiology at the Hans-Knöll-Institute, Friedrich-Schiller-Universität Jena, Winzerlaer Strasse 2, 07745 Jena, Germany.
Usona Institute, Madison Wisconsin 53711, United States.
出版信息
J Nat Prod. 2021 Apr 23;84(4):1403-1408. doi: 10.1021/acs.jnatprod.1c00087. Epub 2021 Mar 5.
Abstract
A novel analogue of psilocybin was produced by hybrid chemoenzymatic synthesis in sufficient quantity to enable bioassay. Utilizing purified 4-hydroxytryptamine kinase from , chemically synthesized 5-methylpsilocin () was enzymatically phosphorylated to provide 5-methylpsilocybin (). The zwitterionic product was isolated from the enzymatic step with high purity utilizing a solvent-antisolvent precipitation approach. Subsequently, was tested for psychedelic-like activity using the mouse head-twitch response assay, which indicated activity that was more potent than the psychedelic dimethyltryptamine, but less potent than that of psilocybin.
摘要
通过混合化学酶合成方法制备了一种新型的裸盖菇素类似物，其产量足以进行生物测定。利用从 中纯化得到的 4-羟色胺激酶，将化学合成的 5-甲基色胺（）进行酶磷酸化，得到 5-甲基裸盖菇素（）。通过溶剂-反溶剂沉淀方法，从酶反应步骤中以高纯度分离得到两性离子产物。随后，使用小鼠头部抽搐反应试验测试了 的致幻样活性，结果表明其活性强于致幻剂二甲基色胺，但弱于裸盖菇素。
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