Pathway Tools
Intro Tutorial
discounted registration ends Sept 5, 2015 (Sat)
Pathway Tools
Intro Tutorial
discounted registration ends Sept 5, 2015 (Sat)
Pathway Tools
Intro Tutorial
discounted registration ends Sept 5, 2015 (Sat)
Pathway Tools
Intro Tutorial
discounted registration ends Sept 5, 2015 (Sat)
Pathway Tools
Intro Tutorial
discounted registration ends Sept 5, 2015 (Sat)
twitter

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:

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

Citations: [Guhling06, Herrera98, Shibuya99, Zhang03i, Hayashi04a, Basyuni07]

Gene-Reaction Schematic: ?

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

Hayashi04a: 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

Zhang03i: 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 19.0 on Fri Sep 4, 2015, biocyc13.