Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 47, Pages 14913-14917Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201708474
Keywords
biosynthesis; crystal structure; cyclization; head-to-middle condensation; terpene synthases
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Funding
- Photon Factory Program Advisory Committee [2010G004, 2012G019, 2014G106]
- JSPS KAKENHI [26292058, 16H06453, 17H05448, 15K12758]
- JSPS A3 Foresight Program
- [15J10131]
- Grants-in-Aid for Scientific Research [15K12758, 16H06453, 15J10131, 26292058, 17H05448] Funding Source: KAKEN
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We report the three-dimensional structure of cyclolavandulyl diphosphate (CLPP) synthase (CLDS), which consecutively catalyzes the condensation of two molecules of dimethylallyl diphosphate (DMAPP) followed by cyclization to form a cyclic monoterpene, CLPP. The structures of apo-CLDS and CLDS in complex with Tris, pyrophosphate, and Mg2+ ion were refined at 2.00 angstrom resolution and 1.73 angstrom resolution, respectively. CLDS adopts a typical fold for cis-prenyl synthases and forms a homo-dimeric structure. An invitro reaction using a regiospecifically H-2-substituted DMAPP substrate revealed the intramolecular proton transfer mechanism of the CLDS reaction. The CLDS structure and structure-based mutagenesis provide mechanistic insights into this unprecedented terpene synthase. The combination of structural and mechanistic insights advances the knowledge of intricate terpene synthase-catalyzed reactions.
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