KEGG   ENZYME: 4.2.3.227
Entry
EC 4.2.3.227                Enzyme                                 
Name
(-)-alpha-cedrene synthase;
EAS3 (gene name);
EAS4 (gene name)
Class
Lyases;
Carbon-oxygen lyases;
Acting on phosphates
Sysname
(2Z,6E)-farnesyl-diphosphate diphosphate-lyase (cyclizing, (-)-alpha-cedrene-forming)
Reaction(IUBMB)
(2Z,6E)-farnesyl diphosphate = (-)-alpha-cedrene + diphosphate [RN:R13311]
Reaction(KEGG)
R13311
Substrate
(2Z,6E)-farnesyl diphosphate [CPD:C16826]
Product
(-)-alpha-cedrene [CPD:C22909];
diphosphate [CPD:C00013]
Comment
The enzyme occurs in plants. The initial cyclization product is a (7R)-beta-bisabolyl cation. (-)-alpha-Cedrene is one of the major products. Other products are (+)-2-epi-prezizaene (cf. EC 4.2.3.226, (+)-2-epi-prezizaene synthase), small amounts of (+)-beta-curcumene, and other sesquiterpenes with less than 10% yield. The enzyme from Nicotiana tabacum (tobacco) also catalyses the reaction of EC 4.2.3.61, 5-epiaristolochene synthase.
History
EC 4.2.3.227 created 2024
Orthology
K15804  5-epiaristolochene/(+)-2-epi-prezizaene/(-)-alpha-cedrene synthase
Genes
SSTN: 125843948 125843949 125844385 125844595
SDUL: 129886310 129886325
LBB: 132615708 132615734 132615770 132615849
NTA: 107821548 142165746 142165747 142165748 142167922 142167925 142167926 142167927 142167928 142167929 142167930
NSY: 104229039
NTO: 104091728
NAU: 109214804
EGT: 105951625
SSPL: 121781268
SMIL: 130986755 130986770 130986772
SHIS: 125194568 125194572 125197460
APAN: 127258817
PEBU: 140827795 140827797 140827809 140827811 140835028 140835030 140835546
PTAB: 142547644
CARB: 113705893
DLT: 127812843 127813191
 » show all
Reference
1  [PMID:20175559]
  Authors
Noel JP, Dellas N, Faraldos JA, Zhao M, Hess BA Jr, Smentek L, Coates RM, O'Maille PE.
  Title
Structural elucidation of cisoid and transoid cyclization pathways of a sesquiterpene synthase using 2-fluorofarnesyl diphosphates.
  Journal
ACS Chem Biol 5:377-92 (2010)
DOI:10.1021/cb900295g
  Sequence
[ag:AAA19216]
Reference
2  [PMID:20201526]
  Authors
Faraldos JA, O'Maille PE, Dellas N, Noel JP, Coates RM.
  Title
Bisabolyl-derived sesquiterpenes from tobacco 5-epi-aristolochene synthase-catalyzed cyclization of (2Z,6E)-farnesyl diphosphate.
  Journal
J Am Chem Soc 132:4281-9 (2010)
DOI:10.1021/ja909886q
Other DBs
ExplorEnz - The Enzyme Database: 4.2.3.227
IUBMB Enzyme Nomenclature: 4.2.3.227
ExPASy - ENZYME nomenclature database: 4.2.3.227
BRENDA, the Enzyme Database: 4.2.3.227

  All links  
Protein sequence (2)   
   UniProt (1)   
   SWISS-PROT (1)   
All databases (2)   

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