期刊
JOURNAL OF NATURAL PRODUCTS
卷 84, 期 4, 页码 1403-1408出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.jnatprod.1c00087
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资金
- Deutsche Forschungsgemeinschaft (DFG) [HO2515/7-1]
- National Institute on Drug Abuse (NIDA) [R01 DA041336]
- Usona Institute (Madison, WI, USA)
A novel analogue of psilocybin was produced through hybrid chemoenzymatic synthesis and tested for psychedelic-like activity, showing potency between dimethyltryptamine and psilocybin.
A novel analogue of psilocybin was produced by hybrid chemoenzymatic synthesis in sufficient quantity to enable bioassay. Utilizing purified 4-hydroxytryptamine kinase from Psilocybe cubensis, chemically synthesized 5-methylpsilocin (2) was enzymatically phosphorylated to provide 5-methylpsilocybin (1). The zwitterionic product was isolated from the enzymatic step with high purity utilizing a solvent-antisolvent precipitation approach. Subsequently, 1 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.
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