KEGG   ENZYME: 5.4.99.41Help
Entry
EC 5.4.99.41                Enzyme                                 

Name
lupeol synthase;
LUPI;
BPW;
RcLUS
Class
Isomerases;
Intramolecular transferases;
Transferring other groups
BRITE hierarchy
Sysname
(3S)-2,3-epoxy-2,3-dihydrosqualene mutase (cyclizing, lupeol-forming)
Reaction(IUBMB)
(3S)-2,3-epoxy-2,3-dihydrosqualene = lupeol [RN:R06466]
Reaction(KEGG)
Substrate
(3S)-2,3-epoxy-2,3-dihydrosqualene [CPD:C01054]
Product
lupeol [CPD:C08628]
Comment
Also forms some beta-amyrin. The recombinant enzyme from Arabidopsis thaliana [3] gives a 1:1 mixture of lupeol and lupan-3beta,20-diol with small amounts of beta-amyrin, germanicol, taraxasterol and psi-taraxasterol. See EC 4.2.1.128 (lupan-3beta,20-diol synthase).
History
EC 5.4.99.41 created 2011
Pathway
ec00909  Sesquiterpenoid and triterpenoid biosynthesis
ec01110  Biosynthesis of secondary metabolites
Orthology
K15815  lupeol synthase 2
K15816  lupeol synthase 1
K20659  lupeol synthase
Genes
ATH: AT1G78960(LUP2) AT1G78970(LUP1)
ALY: ARALYDRAFT_477065 ARALYDRAFT_894488 ARALYDRAFT_895800
CRB: 17894179 17894180
EUS: EUTSA_v10018166mg EUTSA_v10022563mg
BRP: 103830506 103832374
BNA: 106354658
CPAP: 110811355
TCC: 18589606 18595384
GRA: 105772660 105774382
GHI: 107944512 107962932
EGR: 104437295
CAM: 101514106
LANG: 109344416
FVE: 101308521
PPER: 18771897
PMUM: 103339316
RCU: 8280320
JCU: 105634775
HBR: 110651734
POP: 7496060
VVI: 100241546
SLY: 101265842
SPEN: 107024535
SOT: 102583547
CANN: 107877838
NTA: 107822584
NSY: 104234415
INI: 109170366
HAN: 110940172
LSV: 111880217
BVG: 104886793
SOE: 110783899
NNU: 104593853
 » show all
Taxonomy
Reference
1  [PMID:9883589]
  Authors
Herrera JB, Bartel B, Wilson WK, Matsuda SP
  Title
Cloning and characterization of the Arabidopsis thaliana lupeol synthase gene.
  Journal
Phytochemistry 49:1905-11 (1998)
DOI:10.1016/S0031-9422(98)00366-5
  Sequence
[ath:AT1G78970]
Reference
2  [PMID:10542078]
  Authors
Shibuya M, Zhang H, Endo A, Shishikura K, Kushiro T, Ebizuka Y
  Title
Two branches of the lupeol synthase gene in the molecular evolution of plant oxidosqualene cyclases.
  Journal
Eur J Biochem 266:302-7 (1999)
DOI:10.1046/j.1432-1327.1999.00875.x
Reference
3  [PMID:10930257]
  Authors
Segura MJ, Meyer MM, Matsuda SP
  Title
Arabidopsis thaliana LUP1 converts oxidosqualene to multiple triterpene alcohols  and a triterpene diol.
  Journal
Org Lett 2:2257-9 (2000)
DOI:10.1021/ol006016b
  Sequence
[ath:AT1G78970]
Reference
4  [PMID:12736505]
  Authors
Zhang H, Shibuya M, Yokota S, Ebizuka Y
  Title
Oxidosqualene cyclases from cell suspension cultures of Betula platyphylla var. japonica: molecular evolution of oxidosqualene cyclases in higher plants.
  Journal
Biol Pharm Bull 26:642-50 (2003)
  Sequence
Reference
5  [PMID:15256745]
  Authors
Hayashi H, Huang P, Takada S, Obinata M, Inoue K, Shibuya M, Ebizuka Y
  Title
Differential expression of three oxidosqualene cyclase mRNAs in Glycyrrhiza glabra.
  Journal
Biol Pharm Bull 27:1086-92 (2004)
  Sequence
Reference
6  [PMID:16445885]
  Authors
Guhling O, Hobl B, Yeats T, Jetter R
  Title
Cloning and characterization of a lupeol synthase involved in the synthesis of epicuticular wax crystals on stem and hypocotyl surfaces of Ricinus communis.
  Journal
Arch Biochem Biophys 448:60-72 (2006)
DOI:10.1016/j.abb.2005.12.013
  Sequence
Reference
7  [PMID:17803686]
  Authors
Basyuni M, Oku H, Tsujimoto E, Kinjo K, Baba S, Takara K
  Title
Triterpene synthases from the Okinawan mangrove tribe, Rhizophoraceae.
  Journal
FEBS J 274:5028-42 (2007)
DOI:10.1111/j.1742-4658.2007.06025.x
  Sequence
Other DBs
ExplorEnz - The Enzyme Database: 5.4.99.41
IUBMB Enzyme Nomenclature: 5.4.99.41
ExPASy - ENZYME nomenclature database: 5.4.99.41
BRENDA, the Enzyme Database: 5.4.99.41

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