19_terpene

19_terpene - 30 carbons monoterpenes C 10 diterpene C 20...

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Unformatted text preview: 30 carbons monoterpenes C 10 diterpene C 20 sesquiterpenes C 15 (diphosphate) C10 geranyl C15 farnesyl PP C20 geranylgeranyl PP diterpene C30 squalene C40 carotonoid stereospecific aldol reaction; H + also involves hydrolysis of acetyl-enzyme linkage O H + O O OH O Claisen reaction + EnzSH HO 2 C SCoA SCoA SCoA acetoacetyl-CoA HMG-CoA SCoA SEnz HMG-CoA NADPH EnzSH reduction of O acetyl-CoA O enzyme-bound reductase thioester to aldehyde via hemithioacetal acetyl group OH 6 OH OH OH NADPH 1 5 HO 2 C HO 2 C HO 2 C 3 SCoA OH O 2 4 H mevalonic acid (MVA) mevaldic acid mevaldic acid hemithioacetal sequential phosphorylation of the primary alcohol to a diphosphate stereospecific allylic isomerization; equilibrium 2 x ATP O favors DMAPP O OH OH ATP H + 5 HO P O ADP -CO 2 3 1 isomerase 2 4 H OPP O OPP OPP H g H s ATP facilitates the decarboxylation- dimethylallyl PP elimination. The anticipated isopentenyl PP (IPP) (DMAPP) phosphorylation of the tertiary alcohol to make a better L.G. is apparently not involved....
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19_terpene - 30 carbons monoterpenes C 10 diterpene C 20...

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