KEGG   ENZYME: 4.2.3.22
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
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
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
MXAMXAN_6247
MSDMYSTI_06763
MYMA176_000650
CCXCOCOR_07379(cyc2)
MFULILAB_15255
MMASMYMAC_005982
SURSTAUR_1114(geoA2)
AGEAA314_02305 AA314_08732
AVMJQX13_43635
MBDMEBOL_001975
CFUSCYFUS_002616
SCLsce1440
SCUSCE1572_16350
CCROCMC5_068260
MRMA7982_08001
HOHHoch_1257
NBRO3I_014240
NOZDMB37_34650
NAHF5544_16725
NTCKHQ06_14685
NHUH0264_13605
NYALTV02_19175
SPINKV203_07525
SCOSCO6073(SC9B1.20)
SALBXNR_1297
SMASAVERM_2163(geoA)
SGRSGR_6839(geoA)
SGBWQO_01005
SCBSCAB_20121(geoA)
SSXSACTE_0245
SVLStrvi_9069
SHYSHJG_7148
SHOSHJGH_6908
SRCM271_26075
SMALSMALA_3748
SSOII1A49_22455
SFASfla_6028
SBHSBI_02068
SVESVEN_0269 SVEN_0552
SDVBN159_2274(cyc2)
SALSSLNWT_0774
STRPF750_0540
SFISFUL_319
SCIB446_28510
SALUDC74_4443
SALLSAZ_23610
SLVSLIV_07775(cyc2)
SGUSGLAU_26100
SVTSVTN_02895
STREGZL_04447
SCWTU94_25990
SLDT261_3872
SLCSL103_34365
SXISXIM_51240
STRMM444_26920
STRCAA958_01915
SAMBSAM23877_5788(cyc)
SPRISPRI_6965
SCZABE83_34050
SCXAS200_11935
SRWTUE45_06695(cyc2)
STRFASR50_27725
SLEsle_16070(sle_16070)
SRNA4G23_00120(cyc2)
SPAVSpa2297_25605
STRTA8713_25265
SCLFBB341_26965
SGSAVL59_11955
STSIA4E84_31220
SKYD0C37_08035
SALWCP975_28380 CP975_33095
SGMGCM10017557_17550(cyc2)
SCADDN051_10555
SPHWNFX46_09915
SLSSLINC_6548
SNRSNOUR_19870
SPLULK06_026700
STRDNI25_09000
SNWBBN63_17575
SAUOBV401_22145
SSIAA7J05_08620
SVUB1H20_00605
SPUNBFF78_10710
SGVB1H19_22450
SLAUSLA_0172
SALFSMD44_07198(cyc2)
SALJSMD11_6421(cyc2)
SLXSLAV_09415(cyc1)
STROSTRMOE7_21145
SFKKY5_6300
SNZDC008_27320
SGEDWG14_02009(cyc2)
SRJSRO_1735
SLKSLUN_03000
SDXC4B68_09160
SGDELQ87_08740
SQZFQU76_00840
SCYAEJ357_36215
SASTCD934_06110
SNQCP978_26325
STIRDDW44_29705
SKACP970_09515
SGZC0216_09490
SVNCP980_07125
SNKCP967_32685
SHAWCEB94_31845
SRKFGW37_30680
SFICEIZ62_31190
SGALCP966_28425
SSPODDQ41_30295
SVRCP971_17330
SPADDVK44_16910
SAQUEJC51_36445
SGFHEP81_01918
SCAVCVT27_00465
SSEOD0Z67_23170
SBYH7H31_13965
SRIMCP984_29865
SSUBCP968_07850
SPHVF9278_38075
SCINCP977_03065
SFUGCNQ36_25980
SPACB1H29_08340
STSUB7R87_32680
SCHACP983_09805
SGXH4W23_03680
SCOECP976_33675
SBATG4Z16_14665
SSPBCP982_33700
SNFJYK04_06546(cyc2)
SPLACP981_20875
SBROGQF42_32880
STUIGCM10017668_55740(cyc2)
SATAC5746_02905
SCHFIPT68_28555
SHUNDWB77_03759(cyc2)
SHARHUT13_25895
SCYGS1361_30400(cyc2)
SFEUIM697_32630
SLIAHA039_17755
SDWK7C20_20210
SVDCP969_29395
SCALI6J39_00730
SAUHSU9_018255
SFBCP974_00685
SPRACP972_28320
SPEUCGZ69_02405
SROIIAG44_08725
SGJIAG43_02220
SHKJ2N69_29585
SANUK7396_16690
STRYEQG64_00720
SDDD9753_07640
SACTDMT42_29860
SMAOCAG99_12820
SGOBtest1122_08905 test1122_25330
SINEKI385_24560
SLFJEQ17_12070
SDECL3078_35570
SAOVG3H79_05130
SDURM4V62_08365
SYANNRK68_27210
SCTSCAT_2953(cyc)
SCYSCATT_29440
KSKKSE_46080(geoA)
KABB7C62_00490
KAUB6264_12330
KITCFP65_0675 CFP65_6829
STRIC7M71_007765
YIALO772_26615
STRHGXP74_15410
KFLKfla_4247
NGVCDO52_17055
STRREKD16_02015(cyc2)
ACTWF7P10_28090
AGRAAGRA3207_002480
SROSros_0075
NOABKM31_47430
NOWGBF35_49900
NCXNocox_40695(cyc2)
NGNLCN96_09125 LCN96_54695
FRAFrancci3_4231
FREFranean1_5559
FRIFraEuI1c_3502
FALFRAAL6507
SENSACE_3187 SACE_3977 SACE_4907
SACGFDZ84_36100
AMDAMED_1325
AMNRAM_06720
AMMAMES_1317
AMZB737_1318
AOIAORI_7417
AJAAJAP_38785
AMYCCU254_05185
AMYBBKN51_30485
AABA4R43_38405
AMYYYIM_39645(cyc2)
AORISD37_03385
AACDLWP59_11790
APRTMUY14_30005
AROONQK81_28485
APRECNX65_04920
AMIAmir_0977
SESPBN6_11180(geoA)
SSYIEKG83_05700
KALKALB_676 KALB_677
KPHYAOZ06_40930
LEDBBK82_06540
ALOCRK56063
PMADBAY61_21455
ACTUActkin_00570(cyc2)
PSUUPsuf_085020(cyc2)
CATICS0771_03970(cyc2)
DVCDvina_35855
CAICaci_6200
SNASnas_1127
GLYK3N28_04695
AEYCDG81_12895
NPUNpun_R2756
NEDHUN01_24355
CSGCylst_4391
CALOCal7507_2995
DHTNG743_19380
KBSEPA93_38090
 » show all
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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