Metabolic Modeling Tutorial
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Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
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MetaCyc Reaction: 5.4.99.41

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

EC Number: 5.4.99.41

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

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 4.2.1.128 (lupan-3β,20-diol synthase).

Citations: [Guhling06, Herrera98, Shibuya99, Zhang03n, Hayashi04, Basyuni07]

Gene-Reaction Schematic: ?

Unification Links: KEGG:R06466 , Rhea:31386

Relationship Links: BRENDA:EC:5.4.99.41 , ENZYME:EC:5.4.99.41 , IUBMB-ExplorEnz:EC:5.4.99.41

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


References

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

Zhang03n: 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


Report Errors or Provide Feedback
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 18.5 on Sun Nov 23, 2014, biocyc14.