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MetaCyc Reaction: 4.1.99.16

Superclasses: Reactions Classified By Conversion TypeSimple ReactionsChemical Reactions
Reactions Classified By SubstrateSmall-Molecule Reactions

EC Number: 4.1.99.16

Enzymes and Genes:

Streptomyces coelicolor: geosmin synthaseInferred from experiment: cyc2

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 direction shown, i.e. which substrates are on the left and right sides, 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): 1.5170002Inferred 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: [Jiang06a, Cane06, Jiang07a ]

Gene-Reaction Schematic

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

Jiang06a: 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 Pathway Tools version 19.5 (software by SRI International) on Sun May 1, 2016, biocyc14.