MetaCyc Reaction:

Superclasses: Reactions Classified By Conversion Type Simple Reactions Chemical Reactions
Reactions Classified By Substrate Small-Molecule Reactions

EC Number:

Enzymes and Genes:

Arabidopsis thaliana col : lupeol/lupan-3β,20-diol synthase Inferred from experiment : LUP1
multifunctional triterpene synthase Inferred from experiment : PEN6
Betula platyphylla japonica : lupeol synthase Inferred from experiment : OSCBPW
Bruguiera gymnorhiza : lupeol synthase Inferred from experiment : BgLUS
Kandelia candel : triterpene synthase Inferred from experiment : KcMS
Rhizophora stylosa : triterpene synthase Inferred from experiment : RsM1
triterpene synthase Inferred from experiment : RsM2

In Pathway: mangrove triterpenoid biosynthesis , pentacyclic triterpene biosynthesis , lupeol biosynthesis

The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, is in accordance with the Enzyme Commission system.

Mass balance status: Balanced.

Enzyme Commission Primary Name: lupeol synthase

Enzyme Commission Synonyms: LUPI, BPW, RcLUS

Standard Gibbs Free Energy (ΔrG in kcal/mol): -120.3 Inferred by computational analysis [Latendresse13]

Enzyme Commission Summary:
Also forms some β-amyrin. The recombinant enzyme from Arabidopsis thaliana [Segura00] gives a 1:1 mixture of lupeol and lupan-3β,20-diol with small amounts of β-amyrin, germanicol, taraxasterol and Ψ-taraxasterol. See EC (lupan-3β,20-diol synthase).

Citations: [Guhling06, Herrera98, Shibuya99, Zhang03p, Hayashi04, Basyuni07]

Gene-Reaction Schematic: ?

Gene-Reaction Schematic

Unification Links: KEGG:R06466 , Rhea:31386

Relationship Links: BRENDA:EC: , ENZYME:EC: , IUBMB-ExplorEnz:EC:

Revised 11-Apr-2011 by Caspi R , SRI International


Basyuni07: Basyuni M, Oku H, Tsujimoto E, Kinjo K, Baba S, Takara K (2007). "Triterpene synthases from the Okinawan mangrove tribe, Rhizophoraceae." FEBS J 274(19);5028-42. PMID: 17803686

Guhling06: Guhling O, Hobl B, Yeats T, Jetter R (2006). "Cloning and characterization of a lupeol synthase involved in the synthesis of epicuticular wax crystals on stem and hypocotyl surfaces of Ricinus communis." Arch Biochem Biophys 448(1-2);60-72. PMID: 16445885

Hayashi04: Hayashi H, Huang P, Takada S, Obinata M, Inoue K, Shibuya M, Ebizuka Y (2004). "Differential expression of three oxidosqualene cyclase mRNAs in Glycyrrhiza glabra." Biol Pharm Bull 27(7);1086-92. PMID: 15256745

Herrera98: Herrera JB, Bartel B, Wilson WK, Matsuda SP (1998). "Cloning and characterization of the Arabidopsis thaliana lupeol synthase gene." Phytochemistry 49(7);1905-11. PMID: 9883589

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Segura00: Segura MJ, Meyer MM, Matsuda SP (2000). "Arabidopsis thaliana LUP1 converts oxidosqualene to multiple triterpene alcohols and a triterpene diol." Org Lett 2(15);2257-9. PMID: 10930257

Shibuya99: Shibuya M, Zhang H, Endo A, Shishikura K, Kushiro T, Ebizuka Y (1999). "Two branches of the lupeol synthase gene in the molecular evolution of plant oxidosqualene cyclases." Eur J Biochem 266(1);302-7. PMID: 10542078

Zhang03p: Zhang H, Shibuya M, Yokota S, Ebizuka Y (2003). "Oxidosqualene cyclases from cell suspension cultures of Betula platyphylla var. japonica: molecular evolution of oxidosqualene cyclases in higher plants." Biol Pharm Bull 26(5);642-50. PMID: 12736505

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 19.0 on Tue Jul 28, 2015, biocyc12.