KEGG ENZYME: 4.2.3.22

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

MXA:

MXAN_6247

MSD:	MYSTI_06763

MYM:	A176_000650

MYX:	QEG98_34370

MLAN:

JY572_33295

CCX:	COCOR_07379(cyc2)

MFU:	LILAB_15255

MMAS:

MYMAC_005982

PPAK:

JY651_27625

SUR:	STAUR_1114(geoA2)

AGE:	AA314_02305 AA314_08732

AVM:	JQX13_43635

MBD:	MEBOL_001975

CFUS:

CYFUS_002616

SCL:

sce1440

SCU:	SCE1572_16350

CCRO:

CMC5_068260

MRM:	A7982_08001

HOH:

Hoch_1257

NANN:

O0S08_24410 O0S08_35550

NBR:	O3I_014240

NOZ:	DMB37_34650

NAH:	F5544_16725

NTC:	KHQ06_14685

NHU:	H0264_13605

NYA:	LTV02_19175

SPIN:

KV203_07525

SCO:	SCO6073(SC9B1.20)

SALB:

XNR_1297

SMA:	SAVERM_2163(geoA)

SGR:	SGR_6839(geoA)

SGB:

WQO_01005

SFI:

SFUL_319

SANL:

KZO11_00565

SGRF:

SGFS_033720

SCYE:

R2B67_35190

SCB:	SCAB_20121(geoA)

SSX:	SACTE_0245

SVL:	Strvi_9069

SHY:

SHJG_7148

SHO:	SHJGH_6908

SRC:	M271_26075

SMAL:

SMALA_3748

SSOI:

I1A49_22455

SFA:

Sfla_6028

SBH:

SBI_02068

SVE:	SVEN_0269 SVEN_0552

SDV:	BN159_2274(cyc2)

SALS:

SLNWT_0774

STRP:

F750_0540

SCI:	B446_28510

SLV:	SLIV_07775(cyc2)

SGU:	SGLAU_26100

SVT:	SVTN_02895

STRE:

GZL_04447

SCW:	TU94_25990

SLD:

T261_3872

SLC:	SL103_34365

SXI:	SXIM_51240

STRM:

M444_26920

STRC:

AA958_01915

SAMB:

SAM23877_5788(cyc)

SPRI:

SPRI_6965

SCZ:	ABE83_34050

SCX:	AS200_11935

SRW:	TUE45_06695(cyc2)

STRF:

ASR50_27725

SLE:	sle_16070(sle_16070)

SRN:	A4G23_00120(cyc2)

SPAV:

Spa2297_25605

STRT:

A8713_25265

SCLF:

BB341_26965

SGS:	AVL59_11955

STSI:

A4E84_31220

SKY:	D0C37_08035

SALW:

CP975_28380 CP975_33095

SGM:	GCM10017557_17550(cyc2)

SCAD:

DN051_10555

SPHW:

NFX46_09915

SLS:	SLINC_6548

SNR:	SNOUR_19870

SALU:

DC74_4443

SALL:

SAZ_23610

SPLU:

LK06_026700

STRD:

NI25_09000

SNW:	BBN63_17575

SAUO:

BV401_22145

SSIA:

A7J05_08620

SVU:	B1H20_00605

SPUN:

BFF78_10710

SGV:	B1H19_22450

SLAU:

SLA_0172

SALF:

SMD44_07198(cyc2)

SALJ:

SMD11_6421(cyc2)

SLX:	SLAV_09415(cyc1)

STRO:

STRMOE7_21145

SFK:

KY5_6300

SNZ:	DC008_27320

SGE:	DWG14_02009(cyc2)

SRJ:

SRO_1735

SLK:	SLUN_03000

SDX:	C4B68_09160

SGD:	ELQ87_08740

SQZ:	FQU76_00840

SCYA:

EJ357_36215

SAST:

CD934_06110

SNQ:	CP978_26325

STIR:

DDW44_29705

SKA:	CP970_09515

SGZ:	C0216_09490

SVN:	CP980_07125

SNK:	CP967_32685

SHAW:

CEB94_31845

SRK:	FGW37_30680

SFIC:

EIZ62_31190

SGAL:

CP966_28425

SSPO:

DDQ41_30295

SVR:	CP971_17330

SPAD:

DVK44_16910

SAQU:

EJC51_36445

SGF:	HEP81_01918

SCAV:

CVT27_00465

SSEO:

D0Z67_23170

SBY:	H7H31_13965

SRIM:

CP984_29865

SSUB:

CP968_07850

SPHV:

F9278_38075

SCIN:

CP977_03065

SFUG:

CNQ36_25980

SPAC:

B1H29_08340

STSU:

B7R87_32680

SCHA:

CP983_09805

SGX:	H4W23_03680

SCOE:

CP976_33675

SBAT:

G4Z16_14665

SSPB:

CP982_33700

SNF:	JYK04_06546(cyc2)

SPLA:

CP981_20875

SBRO:

GQF42_32880

STUI:

GCM10017668_55740(cyc2)

SATA:

C5746_02905

SCHF:

IPT68_28555

SHUN:

DWB77_03759(cyc2)

SHAR:

HUT13_25895

SCYG:

S1361_30400(cyc2)

SFEU:

IM697_32630

SLIA:

HA039_17755

SDW:	K7C20_20210

SVD:	CP969_29395

SCAL:

I6J39_00730

SAUH:

SU9_018255

SFB:	CP974_00685

SPRA:

CP972_28320

SPEU:

CGZ69_02405

SROI:

IAG44_08725

SGJ:	IAG43_02220

SHK:	J2N69_29585

SANU:

K7396_16690

STRY:

EQG64_00720

SDD:	D9753_07640

SACT:

DMT42_29860

SMAO:

CAG99_12820

SGOB:

test1122_08905 test1122_25330

SINE:

KI385_24560

SLF:	JEQ17_12070

SDEC:

L3078_35570

SAOV:

G3H79_05130

SDUR:

M4V62_08365

SYAN:

NRK68_27210

SRUG:

F0345_21565

SAKB:

K1J60_10395

STAA:

LDH80_05320

SNIG:

HEK616_67550(cyc2)

SVIO:

HWN34_07160

SCAE:

IHE65_09900

STUB:

MMF93_09085

SSPN:

LXH13_30640

SCIR:

STRCI_006311

SXT:	KPP03845_105794(cyc2_1)

SLON:

LGI35_33135

SDRZ:

NEH16_29520

STUD:

STRTU_003254

STEE:

F3L20_12610

SGK:	PET44_25485

SANT:

QR300_22810

SYUN:

MOV08_19910

SARG:

HKX69_07350

SJN:	RI060_08975

SCYN:

N8I84_30570

SOV:	QZH56_33735

SFIY:

F0344_33695

SHAU:

K9S39_12905

SKG:	KJK29_07040

SCOA:

QU709_08660

SLAI:

P8A22_36895

SFP:	QUY26_06250

SCHG:

NRO40_01380

STTN:

BSL84_26640

SINN:

ABB07_08020

STRZ:

OYE22_13780

SCAY:

PYS65_07625

KBU:	Q4V64_40395

SARM:

DVA86_30125

SPRF:

K4G22_14025

SLUO:

PS467_20490

STPB:

QR97_22730

SRPA:

HEP86_21980

SCAJ:

O1G22_09880

STRW:

QHG49_08120

STRL:

HEP84_38420(cyc2)

STSD:

HEP87_39335(cyc2)

SRPZ:

HEP85_30390

SCHE:

QRN89_02240

SGLY:

P8A20_35135

SCAT:

P8A18_00935

STII:

DRB96_29850 DRB96_30335

STIC:

DRB89_29630

SCT:	SCAT_2953(cyc)

SCY:	SCATT_29440

KSK:	KSE_46080(geoA)

KAB:	B7C62_00490

KAU:	B6264_12330

KIT:	CFP65_0675 CFP65_6829

KIS:	HUT16_21240

KCH:	O1G21_20655

STRI:

C7M71_007765

YIA:	LO772_26615

STRH:

GXP74_15410

AGLA:

OIE69_19960

AREV:

RVR_2244

KFL:

Kfla_4247

KRI:	OX958_15290

NGV:	CDO52_17055

STRR:

EKD16_02015(cyc2)

ACTW:

F7P10_28090

AGRA:

AGRA3207_002480

AMAZ:

LUW76_35960

ACIR:

OG979_26335

SPIQ:

OHA34_15550 OHA34_15730

ACTQ:

OG417_01085

SRO:

Sros_0075

NOA:	BKM31_47430

NOW:	GBF35_49900

NCX:	Nocox_40695(cyc2)

NGN:	LCN96_09125 LCN96_54695

NFS:	OIE67_45720

MHAI:

OHB01_00735

FRA:	Francci3_4231

FAL:

FRAAL6507

FRE:	Franean1_5559

FRI:	FraEuI1c_3502

SEN:	SACE_3187 SACE_3977 SACE_4907

SACG:

FDZ84_36100

AMD:

AMED_1325

AMN:

RAM_06720

AMM:

AMES_1317

AMZ:

B737_1318

AOI:

AORI_7417

AJA:	AJAP_38785

AMYC:

CU254_05185

AMYB:

BKN51_30485

AAB:	A4R43_38405

AMYY:

YIM_39645(cyc2)

AORI:

SD37_03385

AACD:

LWP59_11790

APRT:

MUY14_30005

AROO:

NQK81_28485

ATHM:

L1857_15985

ARHD:

VSH64_44360

AMOG:

QRX60_04510

ACOR:

LCL61_08875

AMYZ:

HUW46_00589(cyc2)

ACAB:

QRX50_00860

ANW:	QP939_05750

APRE:

CNX65_04920

AMI:

Amir_0977

SESP:

BN6_11180(geoA)

SSYI:

EKG83_05700

KAL:	KALB_676 KALB_677

KUT:	JJ691_71460

KPHY:

AOZ06_40930

LED:	BBK82_06540

ALO:

CRK56063

PMAD:

BAY61_21455

ACTU:

Actkin_00570(cyc2)

CROS:

N8J89_23320

PSUU:

Psuf_085020(cyc2)

CATI:

CS0771_03970(cyc2)

DVC:	Dvina_35855

DMAT:

Dmats_30680

CAI:

Caci_6200

SNA:

Snas_1127

GLY:	K3N28_04695

AEY:	CDG81_12895

NPU:	Npun_R2756

NED:	HUN01_24355

NLK:	NIES25_60050

CSG:	Cylst_4391

CALO:

Cal7507_2995

DHT:	NG743_19380

TTQ:	NIES37_33160

ALAX:

NIES50_53430

SCYT:

SAMD_63780

KBS:	EPA93_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

LinkDB

DBGET integrated database retrieval system