EC 4.2.3.22 - Germacradienol synthase

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IntEnz Enzyme Nomenclature
EC 4.2.3.22

Names

Accepted name:
germacradienol synthase
Other names:
germacradienol/germacrene-D synthase
2-trans,6-trans-farnesyl-diphosphate diphosphate-lyase [(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol-forming]
Systematic name:
(2E,6E)-farnesyl-diphosphate diphosphate-lyase [(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol-forming]

Reaction

Cofactor

Comments:

Requires Mg2+ for activity. H-1si of farnesyl diphosphate is lost in the formation of (1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol. Formation of (−)-germacrene D involves a stereospecific 1,3-hydride shift of H-1si of farnesyl diphosphate. Both products are formed from a common intermediate [2]. Other enzymes produce germacrene D as the sole product using a different mechanism. The enzyme mediates a key step in the biosynthesis of geosmin (see EC 4.1.99.16 geosmin synthase), a widely occurring metabolite of many streptomycetes, bacteria and fungi [2]. Also catalyses the reaction of EC 4.2.3.75, (−)-germacrene D synthase.

Links to other databases

Enzymes and pathways: NC-IUBMB , BRENDA , DIAGRAM , ExplorEnz , ENZYME@ExPASy , KEGG , MetaCyc , UniPathway
Structural data: CSA , EC2PDB
Gene Ontology: GO:0034004 , GO:0052577
UniProtKB/Swiss-Prot:

References

  1. Cane, D.E. and Watt, R.M.
    Expression and mechanistic analysis of a germacradienol synthase from Streptomyces coelicolor implicated in geosmin biosynthesis.
    Proc. Natl. Acad. Sci. USA 100 : 1547-1551 (2003). [PMID: 12556563]
  2. He, X. and Cane, D.E.
    Mechanism and stereochemistry of the germacradienol/germacrene D synthase of Streptomyces coelicolor A3(2).
    J. Am. Chem. Soc. 126 : 2678-2679 (2004). [PMID: 14995166]
  3. Gust, B., Challis, G. L., Fowler, K., Kieser, T. and Chater, K.F.
    PCR-targeted Streptomyces gene replacement identifies a protein domain needed for biosynthesis of the sesquiterpene soil odor geosmin.
    Proc. Natl. Acad. Sci. USA 100 : 1541-1546 (2003). [PMID: 12563033]

[EC 4.2.3.22 created 2006, modified 2011]