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
ec00909  Sesquiterpenoid and triterpenoid biosynthesis
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K10187  germacradienol/geosmin synthase
Genes
CPRA: CPter91_2617
MXA: MXAN_6247
MFU: LILAB_15255
MSD: MYSTI_06763
MYM: A176_000650
MMAS: MYMAC_005982
CCX: COCOR_07379(cyc2)
SUR: STAUR_1114(geoA2)
AGE: AA314_02305 AA314_08732
MBD: MEBOL_001975
SCL: sce1440
HOH: Hoch_1257
SCO: SCO6073(SC9B1.20)
SMA: SAVERM_2163(geoA)
SGR: SGR_6839(geoA)
SGB: WQO_01005
SCB: SCAB_20121(geoA)
SCT: SCAT_2953(cyc)
SFA: Sfla_6028
SBH: SBI_02068
SHY: SHJG_7148
SDV: BN159_2274(cyc2)
SALB: XNR_1297
SALS: SLNWT_0774
STRP: F750_0540
SFI: SFUL_319
SALU: DC74_4443
SALL: SAZ_23610
SLV: SLIV_07775(cyc2)
STRE: GZL_04447
SLD: T261_3872
STRM: M444_26920
SAMB: SAM23877_5788(cyc)
SPRI: SPRI_6965
SRW: TUE45_06695(cyc2)
SLE: sle_16070(sle_16070)
SRN: A4G23_00120(cyc2)
STRD: NI25_09000
SMAL: SMALA_3748
SLAU: SLA_0172
SALF: SMD44_07198(cyc2)
SALJ: SMD11_6421(cyc2)
SLX: SLAV_09415(cyc1)
SFK: KY5_6300
KSK: KSE_46080(geoA)
KFL: Kfla_4247
SRO: Sros_0075
FAL: FRAAL6507
AMD: AMED_1325
AMN: RAM_06720
AMM: AMES_1317
AMZ: B737_1318
AOI: AORI_7417
AMI: Amir_0977
SESP: BN6_11180(geoA)
ALL: CRK56063
CAI: Caci_6200
SNA: Snas_1127
 » 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 100:1547-51 (2003)
DOI:10.1073/pnas.0337625100
  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 126:2678-9 (2004)
DOI:10.1021/ja039929k
  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 100:1541-6 (2003)
DOI:10.1073/pnas.0337542100
  Sequence
[sco:SCO6073]
Other DBs
ExplorEnz - The Enzyme Database: 4.2.3.22
IUBMB Enzyme Nomenclature: 4.2.3.22
ExPASy - ENZYME nomenclature database: 4.2.3.22
BRENDA, the Enzyme Database: 4.2.3.22
CAS: 211049-88-6

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