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
ALY: 
CRB: 
EUS: 
BRP: 
BNA: 
THJ: 
CIT: 
TCC: 
GRA: 
EGR: 
GMX: 
PVU: 
VRA: 
VAR: 
MTR: 
CAM: 
ADU: 
AIP: 
LJA: 
Lj0g3v0102559.1(Lj0g3v0102559.1) Lj0g3v0116739.1(Lj0g3v0116739.1) Lj0g3v0221889.1(Lj0g3v0221889.1) Lj0g3v0244769.1(Lj0g3v0244769.1)
LANG: 
FVE: 
PMUM: 
MDM: 
PXB: 
CSV: 
CMO: 
RCU: 
8277206 8280754(RcSeTPS1) 8280952 8282483(RcSeTPS3) 8289511(RcSeTPS2)
JCU: 
POP: 
VVI: 
SLY: 
SPEN: 
SOT: 
INI: 
SIND: 
BVG: 
NNU: 
DOSA: 
Os08t0139700-01(Os08g0139700)
OBR: 
BDI: 
ATS: 
SBI: 
SORBI_01g034700(SORBIDRAFT_01g034700) SORBI_02g005490(SORBIDRAFT_02g005490) SORBI_03g041000(SORBIDRAFT_03g041000) SORBI_05g019190(SORBIDRAFT_05g019190) SORBI_05g019210(SORBIDRAFT_05g019210) SORBI_07g002990(SORBIDRAFT_07g002990) SORBI_07g003080(SORBIDRAFT_07g003080) SORBI_07g004490(SORBIDRAFT_07g004490) SORBI_07g005130(SORBIDRAFT_07g005130) SORBI_07g020980(SORBIDRAFT_07g020980) SORBI_09g000980(SORBIDRAFT_09g000980)
ZMA: 
SITA: 
PDA: 
EGU: 
MUS: 
ATR: 
CPRA: 
MXA: 
MFU: 
MSD: 
MYM: 
CCX: 
SUR: 
STAUR_1114(geoA2)
AGE: 
SCL: 
SCU: 
CCRO: 
MRM: 
HOH: 
NBR: 
SCO: 
SCO6073(SC9B1.20)
SMA: 
SAV_2163(geoA)
SGR: 
SGR_6839(geoA)
SGB: 
SCB: 
SSX: 
SVL: 
SCT: 
SCY: 
SFA: 
SBH: 
SHY: 
SHO: 
SVE: 
SDV: 
SALB: 
SALS: 
STRP: 
SFI: 
SCI: 
SRC: 
SALU: 
SALL: 
SLV: 
SGU: 
SVT: 
STRE: 
SCW: 
SLD: 
SXI: 
STRM: 
STRC: 
SAMB: 
SPRI: 
SCZ: 
SCX: 
SRW: 
STRF: 
SLE: 
sle_16070(sle_16070)
SRN: 
SPAV: 
SLC: 
STRT: 
SCLF: 
SGS: 
STSI: 
SLS: 
SNR: 
SPLU: 
KSK: 
KSE_46080(geoA)
KFL: 
SRO: 
NOA: 
FRA: 
FRE: 
FRI: 
FAL: 
SEN: 
AMD: 
AMN: 
AMM: 
AMZ: 
AOI: 
AJA: 
AMQ: 
ALU: 
AMI: 
SESP: 
BN6_11180(geoA)
KAL: 
KPHY: 
LED: 
ALL: 
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.
  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.
  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.
  Sequence
[sco:SCO6073]
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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