Category:TP5

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Cisoid synthase first isomerizes C2-C3 double bond to produce the neutral (3'R')- or (3'S')-nerolidyl diphosphate (enzyme-bound) and then ionizes it.
 
Cisoid synthase first isomerizes C2-C3 double bond to produce the neutral (3'R')- or (3'S')-nerolidyl diphosphate (enzyme-bound) and then ionizes it.
  
−
{|
+
{| class="wikitable" style="text-align:right"
−
! Type || Substrate
+
! Substrate || Type || Intermediate
−
| Transoid synthase
+
| rowspan="3"| Farnesyl diphosphate (FPP)<br/>[[Image:Farnesyl_diphosphate.png]]
−
|(2-'trans',6-'trans')-farnesyl diphosphate
+
| Transoid synthase on (2-''trans'',6-''trans'')-FPP<br/>
 +
| [[Image:Farnesyl_cation.png]]
 
|-
 
|-
−
| Cisoid synthase
+
| Cisoid synthase on (2-''cis'',6-''trans'')-FPP<br/>
−
|((2-'cis',6-'trans')-farnesyl diphosphate
+
| (nerolidyl cation)<br/>[[Image:Nerolidyl_cation.png]]
 
|}
 
|}
−
 
  
  

Revision as of 13:16, 22 July 2014

Contents

Sesquiterpene (C15)

Ring configuration

Germacrane


Sesquiterpenes

Biosynthesis

Overview

Two major classes of terpene synthases exist: "transoid" and "cisoid" synthase. Transoid synthase directly ionizes ('trans','trans')-farnesyl diphosphate, whereas Cisoid synthase first isomerizes C2-C3 double bond to produce the neutral (3'R')- or (3'S')-nerolidyl diphosphate (enzyme-bound) and then ionizes it.

Substrate Type Intermediate Farnesyl diphosphate (FPP)
Farnesyl diphosphate.png 		Transoid synthase on (2-trans,6-trans)-FPP
 Farnesyl cation.png
Cisoid synthase on (2-cis,6-trans)-FPP
 (nerolidyl cation)
Nerolidyl cation.png


References


Sesquiterpene Synthase

farnesyl diphosphate
Farnesyl diphosphate.png
Arrow00d35.png
farnesyl cation
Farnesyl cation.png
farnesane, acyclic ones cyclobutane, cyclopentane cyclofarnesan
(E,E)-germacradiene
(E,E)-Germacradienyl cation.png
  • germacrane
    Germacrene A.png
  • lepidozane
    Lepidozane.png
  • bicyclogermacrane
    Bicyclogermacrane.png
eudesmane (= selinane)
Eudesmanyl cation.png
  • cycloeudesmane
    Cycloeudesmane.png
  • elemane ... 7,8 seco form
    Elemene.png
  • emmotin ... 14(10→1) abeo form
    Emmotin.png
  • farfugin ... 14(10→9) abeo form
    Farfugin.png
  • gorgonane 11(7→6) abeo form
    Gorgonane.png
  • oppositane ... 8(7→6) abeo form
    Oppositane.png
  • valerane (= jatamansane) 15(4→5) abeo form
    Valerane.png
vetispiradienyl cation
Vetispiradienyl cation.png
  • vetispiradiene
    Vetispiradiene.png
  • spirovetivane (= vetispirane)
    Spirovetivane.png
eremophilane (= 14(10→5) abeoeudesmane)
Eremophilenyl cation.png
  • aristolochene
    5-epi-Aristolochene.png
  • aristolane ... 6,11-cyclo form
    Aristolane.png
  • chiloscyphane ...8(7→6) abeo form
    Chiloscyphane.png
  • nardosinane ... 11(7→6) abeo form
    Nardosinane.png
  • cacalol ... 14(5→6) abeo form
    Cacalol.png
  • fukinane ... 9(8→7) abeo form
    Fukinane.png Petasites japonicus
  • brasilane
    Brasilane.png
  • thapsane
    Thapsane.png
  • ishwarane
    Ishwarane.png
guaiane
Guaiane.png
  • xanthane ... 4,5 seco form
    Xanthane.png
  • carabrane ... 4,5 seco form
    Carabrane.png
  • pseudoguaiane ... 15(4→5) abeo form
    Pseudoguaiane.png
  • valerenane ... 8(7→6) abeo form
    Valerenane.png

cycloguaiane

  • cubebane ... 1,6-cyclo form
    Cubebane.png
  • ivaxillarane ... 8,10-cyclo form
    Ivaxillarane.png
  • aromadendrane ... 6,11- cyclo form
    Aromadendrane.png
  • rotundane ... 10,12-cyclo form
    Rotundane.png
  • patchoulane ... 1,11-cyclo form
    Patchoulane.png
  • bourbonane ... 6,10-cyclo form
    Bourbonane.png
(E,E)-humulane
(E,E)-Humulyl cation.png
  • bicyclohumulane
    Bicyclohumulane.png
caryophyllane
(E)-beta-Caryophyllene.png
africanane
Africanane.png
drimane
Drimane.png
  • iresin
    Iresin.png
  • coloratane
    Coloratane.png
nerolidyl cation
Nerolidyl cation.png 		bisabolane
Bisabolyl cation.png
  • thujopsane
    (-)-Sesquithujene.png
chamigrane ... 6,11-cyclobisabolane
Chamigrane.png
  • acorane ... 6,10-cyclobisabolane
    Acorane.png
cuparane (= 7,11-cyclobisabolane)
Cuparane.png 		trichothecane [1]
Trichothecane.png
  • gymnomitrane
    Gymnomitrane.png
widdrane
(Z,E)-germacradiene
(Z,E)-Germacradienyl cation.png 		cadinane
Cadinane.png
  • muurolane
    Muurolane.png
  • bulgarane
    Bulgarane.png
  • amorphane
    Amorphane.png
  • calamenene
    Calamenene.png
  • cadalane
    Cadalane.png
  • alliacane ... 2(3→4) abeo cadinane
    Alliacane.png
  • primnatriene ... 2(3→4) abeo cadinane
    Primnatriene.png
  • oplopane ... 3(4→5) abeo cadinane
    Oplopane.png
  • mutisianthol ... 6(7→8) abeo cadinane
    Mutisianthol.png
  • copaane ... 5,10 cyclo cadinane
    Copaane.png
(Z,E)-humulane
(Z,E)-Humulyl cation.png 		himachalane
Himachalane.png
  • lippifoliane
    Lippifoliane.png
  • longipinane
    Longipinane.png
  • longibornane
    Longibornane.png
  • longifolane
    Longifolane.png
protoilludane
Protoilludane.png
  • illudane
    Illudane.png
  • illudalane ... 4,6-secoilludane
    Illudalane.png
  • sterpurane ... 5(6→7)-abeoilludane
    Sterpurane.png
  • isolactarane
    Isolactarane.png
  • merulane
    Merulane.png
  • lactarane
    Lactarane.png
  • marasmane
    Marasmane.png
hirsutane
Hirsutane.png
cycloheptenyl cation
Cycloheptenyl cation.png 		daucane (= carotane)
Daucane.png
  • isodaucane
    Isodaucane.png
furodysin
Furodysin.png
  • furodysinin
    Furodysinin.png
others
pinguisane
Pinguisane.png
picrotoxane
Picrotoxane.png
perforane
Perforane.png
pacifigorgiane
Pacifigorgiane.png
asteriscane
Asteriscane.png
botrydial
Botrydial.png
tricyclic
  • cedrane
    Cedrane.png
  • isocedrane
    Isocedrane.png
  • zizaane
    Zizaane.png
  • prezizaane
    Prezizaane.png
  • clovane
    Clovane.png
  • precapnellane
    Precapnellane.png
  • capnellane
    Capnellane.png
  • pentalenane
    Pentalenane.png
  • silphinane
    Silphinane.png
  • silphiperfoliane
    Silphiperfoliane.png
  • presilphiperfolane
    Presilphiperfolane.png
  • isocomane
    Isocomane.png
  • panasinsane
    Panasinsane.png
  • modhephane
    Modhephane.png
  • quadrane
    Quadrane.png
  • campherenane
    Campherenane.png
  • alpha-santalane
    Alpha-Santalane.png
  • beta-santalane
    Beta-Santalane.png
  • sativane
    Sativane.png
  • helminthosporane
    Helminthosporane.png
  • copacamphane
    Copacamphane.png
  • cyclocopacamphane
    Cyclocopacamphane.png
  • sinularane
    Sinularane.png
  • cyclosinularane
    Cyclosinularane.png

Cite error: <ref> tags exist, but no <references/> tag was found

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