KEGG   ENZYME: 4.2.3.22Help
Entry
EC 4.2.3.22                 Enzyme                                 

Name
germacradienol synthase;
germacradienol/germacrene-D synthase;
2-trans,6-trans-farnesyl-diphosphate diphosphate-lyase [(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol-forming]
Class
Lyases;
Carbon-oxygen lyases;
Acting on phosphates
BRITE hierarchy
Sysname
(2E,6E)-farnesyl-diphosphate diphosphate-lyase [(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol-forming]
Reaction(IUBMB)
(2E,6E)-farnesyl diphosphate + H2O = (1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + diphosphate [RN:R07647]
Reaction(KEGG)
R07647;
(other) R08543
Show
Substrate
(2E,6E)-farnesyl diphosphate [CPD:C00448];
H2O [CPD:C00001]
Product
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol [CPD:C16143];
diphosphate [CPD:C00013]
Comment
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.
History
EC 4.2.3.22 created 2006, modified 2011
Pathway
Sesquiterpenoid and triterpenoid biosynthesis
Metabolic pathways
Biosynthesis of secondary metabolites
Orthology
K10187  
germacradienol/geosmin synthase
K15803  
(-)-germacrene D synthase
Genes
CIT: 
TCC: 
GMX: 
MTR: 
CAM: 
FVE: 
CSV: 
RCU: 
POP: 
POPTR_0001s44080g POPTR_0005s09830g(POPTRDRAFT_558724) POPTR_0011s14600g(POPTRDRAFT_727191) POPTR_0015s09710g(POPTRDRAFT_575250) POPTR_0170s002001
VVI: 
SLY: 
SOT: 
DOSA: 
Os04t0344100-01(Os04g0344100) Os08t0139700-01(Os08g0139700)
BDI: 
SBI: 
SORBI_01g034700(SORBIDRAFT_01g034700) SORBI_01g035460(SORBIDRAFT_01g035460) SORBI_03g041000(SORBIDRAFT_03g041000) SORBI_05g019210(SORBIDRAFT_05g019210) SORBI_07g003080(SORBIDRAFT_07g003080) SORBI_07g005130(SORBIDRAFT_07g005130)
ZMA: 
100125649(tps26) 100273678 542689(IDP70)
SITA: 
FAU: 
MXA: 
MFU: 
MSD: 
CCX: 
SUR: 
STAUR_1114(geoA2)
SCL: 
SCU: 
HOH: 
NBR: 
NNO: 
SCO: 
SCO6073(SC9B1.20)
SMA: 
SAV_2163(geoA)
SGR: 
SGR_6839(geoA)
SCB: 
SSX: 
SVL: 
SCT: 
SCY: 
SFA: 
SBH: 
SHY: 
SHO: 
SVE: 
SDV: 
SALB: 
STRP: 
SFI: 
SCI: 
SRC: 
SALU: 
KSK: 
KSE_46080(geoA)
KFL: 
SRO: 
FRA: 
FRE: 
FRI: 
FAL: 
SEN: 
AMD: 
AMN: 
AMM: 
AMZ: 
AOI: 
AMI: 
SESP: 
BN6_11180(geoA)
KAL: 
CAI: 
SNA: 
NPU: 
CSG: 
CALO: 
 » show all
Taxonomy
Reference
1  [PMID:12556563]
  Authors
Cane DE, Watt RM.
  Title
Expression and mechanistic analysis of a germacradienol synthase from Streptomyces coelicolor implicated in geosmin biosynthesis.
  Journal
Proc. Natl. Acad. Sci. U. S. A. 100 (2003) 1547-51.
  Organism
Streptomyces coelicolor
  Sequence
[sco:SCO6073]
Reference
2  [PMID:14995166]
  Authors
He X, Cane DE.
  Title
Mechanism and stereochemistry of the germacradienol/germacrene D synthase of Streptomyces coelicolor A3(2).
  Journal
J. Am. Chem. Soc. 126 (2004) 2678-9.
  Organism
Streptomyces coelicolor
  Sequence
[sco:SCO6073]
Reference
3  [PMID:12563033]
  Authors
Gust B, Challis GL, Fowler K, Kieser T, Chater KF.
  Title
PCR-targeted Streptomyces gene replacement identifies a protein domain needed for biosynthesis of the sesquiterpene soil odor geosmin.
  Journal
Proc. Natl. Acad. Sci. U. S. A. 100 (2003) 1541-6.
  Organism
Streptomyces coelicolor
Other DBs
ExplorEnz - The Enzyme Database: 
IUBMB Enzyme Nomenclature: 
ExPASy - ENZYME nomenclature database: 
BRENDA, the Enzyme Database: 
CAS: 
211049-88-6

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