Understanding and Engineering the Stereoselectivity of Humulene Synthase.
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Issue Date
2021-06-28
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Show full item recordAbstract
The non-canonical terpene cyclase AsR6 is responsible for the formation of 2E,6E,9E-humulene during the biosynthesis of the tropolone sesquiterpenoid (TS) xenovulene A. The structures of unliganded AsR6 and of AsR6 in complex with an in crystallo cyclized reaction product and thiolodiphosphate reveal a new farnesyl diphosphate binding motif that comprises a unique binuclear Mg2+ -cluster and an essential K289 residue that is conserved in all humulene synthases involved in TS formation. Structure-based site-directed mutagenesis of AsR6 and its homologue EupR3 identify a single residue, L285/M261, that controls the production of either 2E,6E,9E- or 2Z,6E,9E-humulene. A possible mechanism for the observed stereoselectivity was investigated using different isoprenoid precursors and results demonstrate that M261 has gatekeeping control over product formation.Citation
Angew Chem Int Ed Engl. 2021 Jun 28. doi: 10.1002/anie.202106718. Epub ahead of print.Affiliation
HZI,Helmholtz-Zentrum für Infektionsforschung GmbH, Inhoffenstr. 7,38124 Braunschweig, Germany.Publisher
Wiley-VCHPubMed ID
34180566Type
communication
Language
enEISSN
1521-3773ae974a485f413a2113503eed53cd6c53
10.1002/anie.202106718
Scopus Count
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- Creative Commons
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