Trichodiene biosynthesis and the stereochemistry of the enzymatic cyclization of farnesyl pyrophosphate
作者： David E. Cane , Hyun-Joon Ha , Christopher Pargellis , Felix Waldmeier , Stephen Swanson
DOI: 10.1016/0045-2068(85)90027-6
关键词: Chemistry 、 Chemical decomposition 、 Farnesyl pyrophosphate 、 Trichothecium roseum 、 Stereochemistry 、 Walden inversion 、 Moiety 、 Pyrophosphate 、 Enzyme 、 Biosynthesis 、 Organic chemistry 、 Biochemistry 、 Molecular biology 、 Drug discovery
摘要: Abstract Cyclization of trans,trans-[1-3H2,12,13-14C]farnesyl pyrophosphate (2a) by a preparation trichodiene synthetase isolated from the fungus, Trichothecium roseum, gave (5a), which was shown chemical degradation to retain both tritium atoms precursor at C-11. Incubation 1S-[1-3H,12,13-14C]farnesyl (2b) and 1R-[1-3H,12,13-14C]farnesyl (2c) with resulting labeled trichodienes, 5b 5c, established that displacement moiety C-1 formation new C-C bond in takes place net retention configuration. These results are accounted for an isomerization-cyclization mechanism involving intermediacy nerolidyl (4).
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