KEGG   ENZYME: 5.4.99.41
Entry
EC 5.4.99.41                Enzyme                                 
Name
lupeol synthase;
LUPI;
BPW;
RcLUS
Class
Isomerases;
Intramolecular transferases;
Transferring other groups
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)
R06466
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
ATHAT1G78960(LUP2) AT1G78970(LUP1)
CRB17894179 17894180
EUSEUTSA_v10018166mg EUTSA_v10022563mg
BRP103830506 103832374
BNA106354658
CPAP110811355
PVY116105893 116140120
MINC123194247 123194248 123194249 123199220
TCC18589606 18595384
GRA105772660 105774382
GHI107901998 107944512 107962932
GAB108486269 108486446 108486699
DZI111284967 111318516
EGR104437295
GMX100794151 100810400
GSJ114402293 114421101
PVUPHAVU_002G302200g PHAVU_004G178500g
VRA106765073 106766643
VAR108322906 108345867
VUN114178348 114181519
CCAJ109799472 109803947 109804015
APRC113867241
MTRMTR_6g034985 MTR_6g093180
CAM101514106
ADU107474563 107490028 107490080 107490082 107490083 107490087 107490112
AIP107641335 107641345 107642153 107644502 107644510 107644513
AHF112729284 112747247 112747248 112751369 112751374 112751378 112799770 112801977 112801978 112801979 112801982 112801990
LANG109344416 109351963
FVE101308521
RCN112197150 112198241
PPER18771897
PMUM103339316
PDUL117620888
MNT21387439 21394590 21396873
RCU8280320
JCU105634775
HBR110650225 110651734
MESC110613016
POP7496060
PEU105132608
JRE108989535 108989538 108989546 108993024 108993142 108993143 108993144 118343676
QSU111991790 112005544 112005545
QLO115966272 115967540 115969538
TWL120001583
VVI100241546
VRI117925485
SLY101265842
SPEN107024535
SOT102583547
CANN107877838
NTA107822584
NSY104234415
INI109170366 109184947
ITR116033081
EGT105969755 105970991
SSPL121796209
HAN110940172
ECAD122606550
LSV111880217
CCAV112507013
BVG104886793
SOE110783899
CQI110683768
NNU104593853
 » show all
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)
DOI:10.1248/bpb.26.642
  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)
DOI:10.1248/bpb.27.1086
  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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