Category:TP5
From Metabolomics.JP
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=={{Bilingual|生合成|Biosynthesis}}== | =={{Bilingual|生合成|Biosynthesis}}== | ||
==={{Bilingual|概要|Overview}}=== | ==={{Bilingual|概要|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. | ||
+ | |||
+ | {| class="wikitable" style="text-align:right" | ||
+ | ! Substrate || Type || Intermediate | ||
+ | |- | ||
+ | | rowspan="2"| Farnesyl diphosphate (FPP)<br/>[[Image:Farnesyl_diphosphate.png]] | ||
+ | | Transoid synthase on (2-''trans'',6-''trans'')-FPP<br/> | ||
+ | | [[Image:Farnesyl_cation.png]] | ||
+ | |- | ||
+ | | Cisoid synthase on (2-''cis'',6-''trans'')-FPP<br/> | ||
+ | | (nerolidyl cation)<br/>[[Image:Nerolidyl_cation.png]] | ||
+ | |} | ||
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<!---FARNESYL---> | <!---FARNESYL---> | ||
|- | |- | ||
− | |rowspan="7" align="center"| farnesyl cation<br/>[[Image:Farnesyl cation.png|100px]] | + | |rowspan="7" align="center" valign="top"| farnesyl cation<br/>[[Image:Farnesyl cation.png|100px]] |
|colspan="2"| | |colspan="2"| | ||
{| | {| | ||
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|} | |} | ||
|- | |- | ||
− | |rowspan="3"|(E,E)-germacradiene<br/>[[Image:(E,E)-Germacradienyl cation.png | + | |rowspan="3" valign="top"|(E,E)-germacradiene<br/>[[Image:(E,E)-Germacradienyl cation.png]] |
+ | <hr style="border:dashed"/> | ||
* germacrane<br/>[[Image:Germacrene A.png|90px]] | * germacrane<br/>[[Image:Germacrene A.png|90px]] | ||
* lepidozane<br/>[[Image:Lepidozane.png|90px]] | * lepidozane<br/>[[Image:Lepidozane.png|90px]] | ||
* bicyclogermacrane<br/>[[Image:Bicyclogermacrane.png|90px]] | * bicyclogermacrane<br/>[[Image:Bicyclogermacrane.png|90px]] | ||
− | | eudesmane (= selinane)<br/>[[Image:Eudesmanyl cation.png | + | | eudesmane (= selinane)<br/>[[Image:Eudesmanyl cation.png]]<!---[[Image:beta-Selinene.png|80px]]--> |
+ | <hr style="border:dashed"/> | ||
* cycloeudesmane<br/>[[Image:Cycloeudesmane.png|85px]] | * cycloeudesmane<br/>[[Image:Cycloeudesmane.png|85px]] | ||
* elemane ... 7,8 seco form<br/>[[Image:Elemene.png|85px]] | * elemane ... 7,8 seco form<br/>[[Image:Elemene.png|85px]] | ||
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* oppositane ... 8(7→6) abeo form<br/>[[Image:Oppositane.png|85px]] | * oppositane ... 8(7→6) abeo form<br/>[[Image:Oppositane.png|85px]] | ||
* valerane (= jatamansane) 15(4→5) abeo form<br/>[[Image:Valerane.png|85px]] | * valerane (= jatamansane) 15(4→5) abeo form<br/>[[Image:Valerane.png|85px]] | ||
− | | | + | |valign="top"|vetispiradienyl cation<br/>[[Image:Vetispiradienyl_cation.png|90px]] |
+ | <hr style="border:dashed"/> | ||
* vetispiradiene<br/>[[Image:Vetispiradiene.png|80px]] | * vetispiradiene<br/>[[Image:Vetispiradiene.png|80px]] | ||
* spirovetivane (= vetispirane)<br/>[[Image:Spirovetivane.png|80px]] | * spirovetivane (= vetispirane)<br/>[[Image:Spirovetivane.png|80px]] | ||
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* zizaane<br/>[[Image:Zizaane.png|80px]] | * zizaane<br/>[[Image:Zizaane.png|80px]] | ||
* prezizaane<br/>[[Image:Prezizaane.png|80px]] | * prezizaane<br/>[[Image:Prezizaane.png|80px]] | ||
+ | * clovane<br/>[[Image:Clovane.png|80px]] | ||
+ | * precapnellane<br/>[[Image:Precapnellane.png|80px]] | ||
+ | * capnellane<br/>[[Image:Capnellane.png|80px]] | ||
+ | * pentalenane<br/>[[Image:Pentalenane.png|80px]] | ||
+ | * silphinane<br/>[[Image:Silphinane.png|80px]] | ||
+ | * silphiperfoliane<br/>[[Image:Silphiperfoliane.png|80px]] | ||
+ | * presilphiperfolane<br/>[[Image:Presilphiperfolane.png|80px]] | ||
+ | * isocomane<br/>[[Image:Isocomane.png|80px]] | ||
+ | * panasinsane<br/>[[Image:Panasinsane.png|80px]] | ||
+ | * modhephane<br/>[[Image:Modhephane.png|80px]] | ||
+ | * quadrane<br/>[[Image:Quadrane.png|80px]] | ||
+ | * campherenane<br/>[[Image:Campherenane.png|80px]] | ||
+ | * alpha-santalane<br/>[[Image:alpha-Santalane.png|80px]] | ||
+ | * beta-santalane<br/>[[Image:beta-Santalane.png|80px]] | ||
+ | * sativane<br/>[[Image:Sativane.png|80px]] | ||
+ | * helminthosporane<br/>[[Image:Helminthosporane.png|80px]] | ||
+ | * copacamphane<br/>[[Image:Copacamphane.png|80px]] | ||
+ | * cyclocopacamphane<br/>[[Image:Cyclocopacamphane.png|80px]] | ||
+ | * sinularane<br/>[[Image:Sinularane.png|80px]] | ||
+ | * cyclosinularane<br/>[[Image:Cyclosinularane.png|80px]] | ||
|- | |- | ||
|} | |} |
Latest revision as of 13:17, 22 July 2014
Contents |
[edit] Sesquiterpene (C15)
[edit] Ring configuration
[edit] Germacrane
[edit] Sesquiterpenes
[edit] Biosynthesis
[edit] 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) |
Transoid synthase on (2-trans,6-trans)-FPP |
|
Cisoid synthase on (2-cis,6-trans)-FPP |
(nerolidyl cation) |
- References
[edit] Sesquiterpene Synthase
farnesyl diphosphate | ||||||||
farnesyl cation |
| |||||||
(E,E)-germacradiene |
eudesmane (= selinane) |
vetispiradienyl cation | ||||||
eremophilane (= 14(10→5) abeoeudesmane)
| ||||||||
guaiane |
cycloguaiane | |||||||
(E,E)-humulane |
caryophyllane | |||||||
africanane | ||||||||
drimane |
||||||||
nerolidyl cation |
bisabolane |
chamigrane ... 6,11-cyclobisabolane | ||||||
cuparane (= 7,11-cyclobisabolane)
|
trichothecane [1]
| |||||||
(Z,E)-germacradiene |
cadinane | |||||||
(Z,E)-humulane |
himachalane | |||||||
protoilludane |
hirsutane | |||||||
cycloheptenyl cation |
daucane (= carotane) | |||||||
furodysin | ||||||||
others |
|
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