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
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
twitter

MetaCyc Reaction: 4.1.99.16

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

EC Number: 4.1.99.16

Enzymes and Genes:
geosmin synthase Inferred from experiment : cyc2 ( Streptomyces coelicolor )

In Pathway: geosmin biosynthesis

Note that this reaction equation differs from the official Enzyme Commission reaction equation for this EC number, which can be found here .

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: geosmin synthase

Standard Gibbs Free Energy (ΔrG in kcal/mol): 1.5170002 Inferred by computational analysis [Latendresse13]

Summary:
Require Mg2+. Geosmin is the cause of the characteristic smell of moist soil. It is a bifunctional enzyme. The N-terminal part of the enzyme is EC 4.2.3.22, germacradienol synthase, and forms (1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol from FPP. The C-terminal part of the enzyme catalyses the conversion of germacradienol to geosmin via (8S,9S,10S)-8,10-dimethyl-1-octalin.

The full reaction catalyzed by the C-terminal part of the enzyme is

(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O = (-)-geosmin + acetone

Enzyme Commission Summary:
Require Mg2+. Geosmin is the cause of the characteristic smell of moist soil. It is a bifunctional enzyme. The N-terminal part of the enzyme is EC 4.2.3.22, germacradienol synthase, and forms (1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol from FPP. The C-terminal part of the enzyme catalyses the conversion of germacradienol to geosmin via (8S,9S,10S)-8,10-dimethyl-1-octalin.

The reaction shown here is the summary of the following two reactions:

(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol → (8S,9S,10S)-8,10-dimethyl-1-octalin + acetone

(8S,9S,10S)-8,10-dimethyl-1-octalin + H2O → (-)-geosmin

Citations: [Jiang06, Cane06, Jiang07a]

Gene-Reaction Schematic: ?

Unification Links: Rhea:30458

Relationship Links: BRENDA:EC:4.1.99.16 , ENZYME:EC:4.1.99.16 , IUBMB-ExplorEnz:EC:4.1.99.16

Credits:
Revised 14-Mar-2011 by Caspi R , SRI International


References

Cane06: Cane DE, He X, Kobayashi S, Omura S, Ikeda H (2006). "Geosmin biosynthesis in Streptomyces avermitilis. Molecular cloning, expression, and mechanistic study of the germacradienol/geosmin synthase." J Antibiot (Tokyo) 59(8);471-9. PMID: 17080683

Jiang06: Jiang J, He X, Cane DE (2006). "Geosmin biosynthesis. Streptomyces coelicolor germacradienol/germacrene D synthase converts farnesyl diphosphate to geosmin." J Am Chem Soc 128(25);8128-9. PMID: 16787064

Jiang07a: Jiang J, He X, Cane DE (2007). "Biosynthesis of the earthy odorant geosmin by a bifunctional Streptomyces coelicolor enzyme." Nat Chem Biol 3(11);711-5. PMID: 17873868

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


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 Tue Nov 25, 2014, biocyc14.