Journal
ORGANIC LETTERS
Volume 19, Issue 7, Pages 1816-1819Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b00586
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Funding
- Natural Science Foundation of China [31670099, 41476063, 31470387]
- Development Project of CAS Center for Excellence in Molecular Plant Sciences [CEMPS2016004]
- Key Projects of Shanghai Committee of Science and Technology [14JC1406900]
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Two GFPPS linked (+)-tthalianatriene (1) and (-)-retigeranin B (2) sesterterpene synthase genes were identified from the genome of Arabidopsis thaliana. 1 possesses an unprecedented 11-6-5. tricyclic ring system, while 2 contains a characteristic 5-5-5-6-5 pentacyclic ring, system. Their structures were determined by extensive NMR spectroscopy, chemical derivatization, and)c-ray crystallography. The variable-temp NMR measurement of 3, a diepoxy-bearing derivative of 1, enables us to completely assign the NMR signals of the two conformers as 3a (67%, UUU) and 3b (33%, UUD). A plausible biosynthesis mechanism of 1 was proposed.
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