KEGG ENZYME: 4.2.3.152

ENZYME: 4.2.3.152

Entry

EC 4.2.3.152                Enzyme

Name

2-epi-5-epi-valiolone synthase;
AcbC;
ValA;
CetA;
SalQ;
C7-cyclitol synthase

Class

Lyases;
Carbon-oxygen lyases;
Acting on phosphates

Sysname

alpha-D-sedoheptulopyranose-7-phosphate phosphate-lyase (cyclizing; 2-epi-5-epi-valiolone-forming)

Reaction(IUBMB)

alpha-D-sedoheptulopyranose 7-phosphate = 2-epi-5-epi-valiolone + phosphate [RN:R10937]

Reaction(KEGG)

R10937

Substrate

alpha-D-sedoheptulopyranose 7-phosphate [CPD:C20956]

Product

2-epi-5-epi-valiolone [CPD:C17691];
phosphate [CPD:C00009]

Comment

The enzyme is highly specific for alpha-D-sedoheptulopyranose 7-phosphate. It requires a divalent metal ion (Zn2+ or Co2+) and an NAD+ cofactor, which is transiently reduced during the reaction. The enzyme is involved in the biosynthesis of C7N-aminocyclitol natural products, such as the valienamine moiety of the antidiabetic drug acarbose and the crop protectant validamycin A. cf. EC 4.2.3.155, 2-epi-valiolone synthase and EC 4.2.3.154, demethyl-4-deoxygadusol synthase.

History

EC 4.2.3.152 created 2015, modified 2016

Pathway

ec00525

Acarbose and validamycin biosynthesis

ec01100

Metabolic pathways

ec01110

Biosynthesis of secondary metabolites

Orthology

K19969

2-epi-5-epi-valiolone synthase

Genes

GGA:

427594

PCOC:

116239526

MGP:

100539368

CJO:

107319740

TPAI:

128078648

LMUT:

125698926

NMEL:

110404900

APLA:

101799904

AACU:

137862600

ACYG:

106035463

AFUL:

116493131

TGU:

100223651

LSR:

110482179

SCAN:

103817203

PMOA:

120514101

OTC:

121347314

PRUF:

121350577

ATRC:

139595678

GFR:

102035384

FAB:

101811082

OMA:

130258334

PHI:

102106679

PMAJ:

107210122

CCAE:

111935283

CCW:

104683510

CBRC:

103624386

ACOE:

138117322

ETL:

114070867

ZAB:

102064817

ZLE:

135453101

ACHL:

103801835

SVG:

106850319

MMEA:

130573734

HRT:

120758374

SATI:

136366157

CCIC:

134048869

FPG:

101920037

FCH:

102050204

CCRI:

104164038

NNT:

104409957

SHAB:

115614837

ACUN:

113484873

TALA:

104367529

ACHC:

115333430

HALD:

104316124

HLE:

104835331

AGEN:

126049928

HHAR:

128136609

BBUT:

142042896

GCL:

127021669

CSTI:

104552976

LDI:

104347205

MNB:

103776754

DPUB:

104308153

PPUS:

135182535

AVIT:

104273426

BRHI:

104498064

EGZ:

104132682

NNI:

104017000

PCRI:

104035587

PCAO:

104052076

PADL:

103921828

AFOR:

103903317

FGA:

104076778

CBOR:

142086022

GSTE:

104261856

CBOY:

140658250

MAME:

142415400

CLV:

102091344

CNIC:

135992879

MUI:

104544300

PGUU:

104472365

PLET:

104625465

EHS:

104510749

CMAC:

104477205

CUCA:

104061234

TEO:

104376370

BREG:

104634411

OHA:

104331381

ACAR:

104529679

CPEA:

104388118

CVF:

104285191

RTD:

128915710

CRID:

134521588

LMIC:

141749465

AROW:

112970521

NPD:

112958684

TGT:

104568935

DNE:

112988914

SCAM:

104140968

PSS:

102457108

CIZ:

142018799

CMY:

114019870

CCAY:

125639654

LKP:

140915156

NDS:

141991378

DCC:

119858416

CPIC:

101935311

TST:

117879969

CABI:

116820414

MRV:

120369070

ACS:

100554413

ASAO:

132766705

PVT:

110077699

SUND:

121921533

VKO:

123034373

PMUA:

114592775

PRAF:

128409616

ZVI:

118081610

HCG:

128343981

XLA:	108714718 108715916

XTR:

100492806

NPR:

108786177

RTEM:

120945168

ACAT:

141102420

PADS:

140337175

BBUF:

120978449

BGAR:

122944258

DTC:

141084791

DRE:	100003999(eevS)

SRX:	107713488 107750277

SANH:

107666977

SGH:

107599439

CCAR:

122145345

CAUA:

113050480

CGIB:

128015848

PTET:

122347017(eevs)

LROH:

127167200(eevs)

GRF:	141347715(eevs)

OMC:	131542646(eevs)

PPRM:

120491286(eevs)

RKG:	130087421(eevs)

MAMB:

125273457(eevs)

CIDE:

127514836

CERY:

137010746(eevs)

MASI:

127445879 127449114

TROS:

130557037(eevs)

TDW:	130425143(eevs)

MANU:

129451277(eevs)

PDAB:

135769895(eevs)

AMEX:

103021483(eevs)

CMAO:

118808674(eevs)

CHAR:

105909950(eevs)

SPIL:

134092718(eevs)

ASAD:

121707308(eevs)

LCO:

104922196

NCC:

104966975

TBEN:

117475577(eevs)

CGOB:

115008684

PGEO:

117446070(eevs)

GACU:

117543702(eevs)

EMAC:

134883515(eevs)

ELY:	117256564(eevs)

EFO:	125895543(eevs)

PLEP:

121949252(eevs)

SLUC:

116036497(eevs)

ECRA:

117944092(eevs)

ESP:

116687339

PFLV:

114553752

GAT:	120835676(eevs)

PPUG:

119194247(eevs)

AFB:	129105646(eevs)

CLUM:

117730389(eevs)

PSWI:

130208770(eevs)

CANA:

137796649(eevs)

CVE:	137870639(eevs)

MSAM:

119885942(eevs)

SCHU:

122865156(eevs)

EARM:

139283442(eevs)

CUD:	121507504(eevs)

SPUL:

138606381(eevs)

LMIX:

132977720(eevs)

HTC:	141789301(eevs)

ALAT:

119021887(eevs)

ASTR:

137595606(eevs)

PKLU:

139219136(eevs)

MZE:

101474077

ONL:

100690451

OAU:	116312421(eevs)

OLA:

101163482

OML:	112144500(eevs)

CSAI:

133449523(eevs)

XCO:

114147843

XHE:

116716424

PRET:

103465590

PFOR:

103129387

PLAI:

106938933

PMEI:

106911441

GAF:	122834119(eevs)

PPRL:

129353593(eevs)

CVG:

107082342

CTUL:

119783636(eevs)

GMU:	124857126(eevs)

NFU:

107385806

AOCE:

111566151(eevs)

EJA:	138206998(eevs)

BFRE:

138630233(eevs)

MCEP:

125007449(eevS)

POV:

109629062

SSEN:

122768842(eevs)

SSOE:

131461101(eevs)

HHIP:

117762080(eevs)

HSP:	118104674(eevs)

PPLT:

128456060(eevs)

SMAU:

118309766(eevs)

LCF:	108896951 108898868(eevs)

SDU:

111221586

SLAL:

111663894 111666010

XGL:	120806967(eevs)

BPEC:

110170184

ENY:	140366164(eevs)

BSPL:

114856132(eevs)

SJO:	128356027(eevs)

SSCO:

133978110(eevs)

TTY:	137182039(eevs)

GMH:

115557688

SASA:

106565742

STRU:

115207554

OTW:

112262555

OMY:

110494594

OGO:

124003813

ONE:

115143401

OKI:

109898101

OKE:	118389454(eevs)

OMM:

135527855

OCLA:

139369887

SALP:

111969394

SNH:

120024847

SFON:

129851125

CCLU:

121575038

ELS:

105017435

OEP:	134022174(eevs)

SFM:

108923353

LOC:

102684922

ARUT:

117964007

AFRA:

136030893

CSL:	COCSUDRAFT_39261

AAF:	AURANDRAFT_3740

SERA:

Ser39006_003950

SERQ:

CWC46_03950

SLIG:

GTU79_24420

PALF:

K6R05_03025

PKQ:	ACEJ41_06035

FSG:	LQ771_06975

RHD:	R2APBS1_3641

RTH:	LRK53_03190

PFC:	PflA506_4591

PEZ:	HWQ56_09190

THAT:

H3N35_23225

TVD:	SG34_025385

PAEW:

KIH87_05110

CJA:

CJA_3250

GPB:	HDN1F_13870(acbC)

CVC:	BKX93_19945

BTZ:

BTL_4163

BOK:

DM82_5622

COF:	FOZ74_00740

MMEI:

LRP31_12225

AVF:	RvVAR031_pl04730(aroB)

MEE:	DA075_19375

SUR:	STAUR_1386(gacC)

AVM:	JQX13_08230 JQX13_41180

CFUS:

CYFUS_007478

PBRU:

LZC95_06515

PALJ:

LZC94_02030

PAUU:

E8A73_036720

TSA:	AciPR4_1231

BBY:	CY96_27945

CBB:

CLD_3207

RPAY:

P0092_07155

MMI:	MMAR_0578(aroB_1)

MMAE:

MMARE11_05350(aroB_1)

MHAD:

B586_06435

MLJ:	MLAC_02190(aroB_1)

CGP:	KBP53_09165

NSR:	NS506_05945

NAH:	F5544_18765

NAD:	NCTC11293_02222(aroB_1)

RER:

RER_54360

REY:

O5Y_25890

REB:	XU06_26170

RHB:

NY08_95

RTM:	G4H71_11885

RHOH:

CPI83_03025

RHS:	A3Q41_04747(aroB_3)

TSM:	ASU32_10315

SRT:

Srot_2448

SHY:

SHJG_0276

SHO:	SHJGH_0110

SALS:

SLNWT_0595

SGU:	SGLAU_01035(gacC)

STRM:

M444_32560

SCZ:	ABE83_10155

SRW:	TUE45_05037(aroB_3)

SLE:	sle_45870(sle_45870)

SCLF:

BB341_29000

SLS:	SLINC_5104

SSIA:

A7J05_03495

SFK:

KY5_0702

SRJ:

SRO_6646

SCYA:

EJ357_02100 EJ357_14575

SAST:

CD934_05045

SNQ:	CP978_00070

SKA:	CP970_39485

SGZ:	C0216_19350

SRK:	FGW37_17500

SFIC:

EIZ62_30660

SSPO:

DDQ41_30765

SGF:	HEP81_06989(gacC)

SPAC:

B1H29_04435

SCYG:

S1361_01415(aroB2)

SAUH:

SU9_022190

SROI:

IAG44_34870

STRY:

EQG64_25575

SGK:	PET44_31000

SCOA:

QU709_45595

STPB:

QR97_23315

STRV:

EZV63_03180

SSIR:

WAB15_07045

SLUA:

AB8735_04290

STGO:

KBP30_02910

STCM:

SCMC78_23110

KIT:	CFP65_6096

KCH:	O1G21_36190

KCM:	ABWK59_26495

KIC:	KCMC57_up13150(aroB_2)

KPUR:

ACFCLZ_30170

STRH:

GXP74_26630 GXP74_28920

XYA:	ET471_00715

CIRA:

LFM56_12025

AER:	AERYTH_07130

NGV:	CDO52_07210

FAL:

FRAAL4639

AOI:	AORI_5447(aroB)

AJA:	AJAP_35530

AMYC:

CU254_12845

AORI:

SD37_10235

ACOR:

LCL61_18255 LCL61_40685

SESP:

BN6_52640

KUT:	JJ691_27080(salQ)

ACTI:

UA75_21530

ACAD:

UA74_21050

STP:	Strop_2345

SAQ:

Sare_2489

MCAB:

HXZ27_14335

ASE:	ACPL_3680(acbC) ACPL_6250

ACTS:

ACWT_3552 ACWT_6118

PLK:	CIK06_12685

PLAB:

C6361_27335

PLAT:

C6W10_29735

PRY:	Prubr_33290

DROS:

Drose_26960

CWO:

Cwoe_1465

GLP:	Glo7428_0525

GDU:	P0S91_09615

» show all

Reference

1 [PMID:10196166]

Authors

Stratmann A, Mahmud T, Lee S, Distler J, Floss HG, Piepersberg W

Title

The AcbC protein from Actinoplanes species is a C7-cyclitol synthase related to 3-dehydroquinate synthases and is involved in the biosynthesis of the alpha-glucosidase inhibitor acarbose.

Journal

J Biol Chem 274:10889-96 (1999)
DOI:10.1074/jbc.274.16.10889

Sequence

[ase:ACPL_3680]

Reference

2 [PMID:16151088]

Authors

Yu Y, Bai L, Minagawa K, Jian X, Li L, Li J, Chen S, Cao E, Mahmud T, Floss HG, Zhou X, Deng Z

Title

Gene cluster responsible for validamycin biosynthesis in Streptomyces hygroscopicus subsp. jinggangensis 5008.

Journal

Appl Environ Microbiol 71:5066-76 (2005)
DOI:10.1128/AEM.71.9.5066-5076.2005

Sequence

[shy:SHJG_0276]

Reference

3 [PMID:17195255]

Authors

Wu X, Flatt PM, Schlorke O, Zeeck A, Dairi T, Mahmud T

Title

A comparative analysis of the sugar phosphate cyclase superfamily involved in primary and secondary metabolism.

Journal

Chembiochem 8:239-48 (2007)
DOI:10.1002/cbic.200600446

Sequence

[ag:ABL74381]

Reference

4 [PMID:18648803]

Authors

Choi WS, Wu X, Choeng YH, Mahmud T, Jeong BC, Lee SH, Chang YK, Kim CJ, Hong SK

Title

Genetic organization of the putative salbostatin biosynthetic gene cluster including the 2-epi-5-epi-valiolone synthase gene in Streptomyces albus ATCC 21838.

Journal

Appl Microbiol Biotechnol 80:637-45 (2008)
DOI:10.1007/s00253-008-1591-2

Sequence

[sals:SLNWT_0595]

Reference

5 [PMID:24832673]

Authors

Kean KM, Codding SJ, Asamizu S, Mahmud T, Karplus PA

Title

Structure of a sedoheptulose 7-phosphate cyclase: ValA from Streptomyces hygroscopicus.

Journal

Biochemistry 53:4250-60 (2014)
DOI:10.1021/bi5003508