期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 59, 期 4, 页码 1450-1454出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201910175
关键词
enzymes; laccase; natural products; phosphatase; psilocybin
资金
- International Leibniz Research School (ILRS) for Microbial Interactions
- Carl Zeiss Foundation
- Deutsche Forschungsgemeinschaft (DFG) [HO2515/71]
- DFG Collaborative Research Center 1127 (ChemBioSys)
Upon injury, psychotropic psilocybin-producing mushrooms instantly develop an intense blue color, the chemical basis and mode of formation of which has remained elusive. We report two enzymes from Psilocybe cubensis that carry out a two-step cascade to prepare psilocybin for oxidative oligomerization that leads to blue products. The phosphatase PsiP removes the 4-O-phosphate group to yield psilocin, while PsiL oxidizes its 4-hydroxy group. The PsiL reaction was monitored by in situ C-13 NMR spectroscopy, which indicated that oxidative coupling of psilocyl residues occurs primarily via C-5. MS and IR spectroscopy indicated the formation of a heterogeneous mixture of preferentially psilocyl 3- to 13-mers and suggest multiple oligomerization routes, depending on oxidative power and substrate concentration. The results also imply that phosphate ester of psilocybin serves a reversible protective function.
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