KEGG ENZYME: 2.3.1.277

ENZYME: 2.3.1.277

Entry

EC 2.3.1.277                Enzyme

Name

phosphorylated butenolide synthase;
2-oxo-3-(phosphooxy)propyl 3-oxoalkanoate synthase;
afsA (gene name);
scbA (gene name);
barX (gene name);
mmfL (gene name)

Class

Transferases;
Acyltransferases;
Transferring groups other than aminoacyl groups

Sysname

3-oxoacyl-[acyl-carrier protein]:glycerone phosphate 3-oxoacyltransferase

Reaction(IUBMB)

a 3-oxoacyl-[acyl-carrier protein] + glycerone phosphate = a (4-alkanoyl-5-oxo-2H-furan-3-yl)methyl phosphate + H2O + a holo-[acyl-carrier protein] (overall reaction) [RN:R13418];
(1a) a 3-oxoacyl-[acyl-carrier protein] + glycerone phosphate = a 2-oxo-3-(phosphooxy)propyl 3-oxoalkanoate + a holo-[acyl-carrier protein] [RN:R12289];
(1b) a 2-oxo-3-(phosphooxy)propyl 3-oxoalkanoate = a (4-alkanoyl-5-oxo-2H-furan-3-yl)methyl phosphate + H2O (spontaneous) [RN:R13419]

Reaction(KEGG)

R12289 R13418 R13419

Substrate

3-oxoacyl-[acyl-carrier protein] [CPD:C00685];
glycerone phosphate [CPD:C00111];
2-oxo-3-(phosphooxy)propyl 3-oxoalkanoate [CPD:C22065]

Product

(4-alkanoyl-5-oxo-2H-furan-3-yl)methyl phosphate [CPD:C21774];
H2O [CPD:C00001];
holo-[acyl-carrier protein] [CPD:C00229];
2-oxo-3-(phosphooxy)propyl 3-oxoalkanoate [CPD:C22065]

Comment

The enzyme catalyses the first committed step in the biosynthesis of gamma-butyrolactone, as well as 2-alkyl-4-hydroxymethylfuran-3-carboxylate (methylenomycin furan) autoregulators that control secondary metabolism and morphological development in Streptomyces bacteria.

History

EC 2.3.1.277 created 2018, modified 2024

Orthology

K22463

2-oxo-3-(phosphooxy)propyl 3-oxoalkanoate synthase

Genes

YRE:	HEC60_12875

TOE:	QMG90_05975

PROD:

PCO85_08030

EPI:	Q3V30_15440

AMAH:

DLM_1345

PBH:	AAW51_3063

MPAG:

C0J29_24015

MAIC:

MAIC_49490

MPAE:

K0O64_03280

MCRO:

MI149_03875

CSX:	CSING_09340

NCY:	NOCYR_1429

NBR:	O3I_009095 O3I_022440 O3I_026160

NNO:	NONO_c59160

NSR:	NS506_05283

NTP:	CRH09_04845 CRH09_10155 CRH09_19790

NOZ:	DMB37_02530 DMB37_29865

NOD:	FOH10_10135

NAH:	F5544_11680

NWL:	NWFMUON74_54410

NIE:	KV110_09630 KV110_16520 KV110_22410

NHU:	H0264_14695

NYA:	LTV02_03870 LTV02_18435

NSPU:

IFM12276_25010

NYU:	D7D52_08100

RHA:	RHA1_ro04614

RER:

RER_54010

REY:

O5Y_25660

REB:	XU06_26000

RQI:	C1M55_27235

ROP:

ROP_45600

ROA:	Pd630_LPD01099 Pd630_LPD06644

RHB:

NY08_569

RAV:	AAT18_22295

RRZ:	CS378_12125

RHQ:	IM25_24585

RHOD:

AOT96_07205

RRT:	4535765_02640

RTM:	G4H71_11170

RKO:	JWS14_25400

RPSK:

JWS13_19140

RGOR:

NMQ04_10800

RHOO:

RA302_26250

RHOU:

KZJ41_23735

RHOW:

A4U64_02265

RHOJ:

JVH1_13180 JVH1_25065

RHOS:

QWW67_12380

RHOQ:

QWW98_12390

RHOY:

QNA09_19645

RHOH:

CPI83_03270

RFA:	A3L23_03815 A3L23_04925

RHS:	A3Q41_04426

REQ:

REQ_44790

WHR:	OG579_14335

GPO:	GPOL_c20770 GPOL_c49040

SCO:	SCO6266(SCAH10.31) SCP1.243(mmfL)

SMA:	SAVERM_2269(avaA)

SGR:	SGR_6889(afsA)

SGB:

WQO_00740

SFI:

SFUL_271

SANL:

KZO11_00310 KZO11_19690

SGRF:

SGFS_035700 SGFS_040850 SGFS_079640 SGFS_079870

SCYE:

R2B67_04425 R2B67_35415

SCB:	SCAB_12081 SCAB_63031 SCAB_63111

SSX:	SACTE_3173 SACTE_6321

SVL:	Strvi_3600

SHY:	SHJG_4004 SHJG_7319 SHJG_8650

SHO:	SHJGH_3769 SHJGH_7079 SHJGH_8410

SRC:	M271_03790 M271_07485

SMAL:

SMALA_6930 SMALA_7619

SSOI:

I1A49_38425 I1A49_41870

SFA:	Sfla_3302 Sfla_6323

SBH:

SBI_08929

SVE:	SVEN_4183 SVEN_5969

SDV:	BN159_2279 BN159_4440

SALS:

SLNWT_0249 SLNWT_2752 SLNWT_4679

STRP:

F750_0224(afsA) F750_3441(afsA)

SLV:	SLIV_06815(afsA)

SGU:	SGLAU_25495

SVT:	SVTN_03085 SVTN_03460 SVTN_29875

STRE:

GZL_00107 GZL_01281 GZL_01594 GZL_09306

SCW:	TU94_11455

SLD:	T261_0487 T261_2144

SLC:	SL103_20520 SL103_26350

SXI:	SXIM_17800

STRM:

M444_36350 M444_36565 M444_38055

SAMB:

SAM23877_0232

SCZ:	ABE83_19750 ABE83_34265

SCX:	AS200_21945 AS200_24410 AS200_44220

SRW:	TUE45_05044 TUE45_pSRc_0609(TUE45_pSRTUE45c_0609)

SLE:	sle_45960(sle_45960)

SRN:	A4G23_05421

SPAV:

Spa2297_32650

STRT:

A8713_01240

SCLF:

BB341_16850 BB341_25515

SGS:	AVL59_00695

STSI:

A4E84_21260

SALW:

CP975_23005

SCAD:

DN051_10570

SPHW:

NFX46_09900 NFX46_12245

SLS:	SLINC_5092 SLINC_6540

SNR:	SNOUR_05455 SNOUR_06740

SALU:

DC74_5978 DC74_7047 DC74_7321 DC74_7607

SALL:

SAZ_30970 SAZ_36560 SAZ_37915 SAZ_39250

SPLU:

LK06_017405

STRD:

NI25_18850

SNW:	BBN63_07420 BBN63_21870 BBN63_24955

SAUO:

BV401_38280

SSIA:

A7J05_00415 A7J05_00570 A7J05_13280 A7J05_36165 A7J05_36320

SVU:	B1H20_00410 B1H20_15505

SPUN:

BFF78_11405

SGV:	B1H19_37530

SLAU:

SLA_3053

SALF:

SMD44_04059 SMD44_04421

SALJ:

SMD11_3339 SMD11_6032

SLX:	SLAV_20865 SLAV_40300

STRO:

STRMOE7_29285 STRMOE7_35135

SFK:

KY5_6104c

SNZ:	DC008_13210 DC008_27305

SGE:	DWG14_02015

SRJ:

SRO_3382

SDX:	C4B68_08540 C4B68_08560

SGD:	ELQ87_36110

SCYA:

EJ357_14630 EJ357_16305 EJ357_35240 EJ357_36165

SAST:

CD934_15305

SNQ:	CP978_34585

STIR:

DDW44_16615 DDW44_31525

SKA:	CP970_10415

SGZ:	C0216_31320 C0216_31805

SNK:	CP967_04275 CP967_15135 CP967_17825 CP967_30545 CP967_30560 CP967_31560

SHAW:

CEB94_20765

SRK:	FGW37_31685

SFIC:

EIZ62_19125 EIZ62_31530

SGAL:

CP966_28410

SSPO:

DDQ41_04315 DDQ41_08110 DDQ41_31065

SVR:	CP971_19130 CP971_26335

SPAD:

DVK44_28100 DVK44_34195

SFY:	GFH48_20475 GFH48_38925

SAQU:

EJC51_22105 EJC51_25725 EJC51_43860

SGF:	HEP81_03594 HEP81_07959

SCAV:

CVT27_00255 CVT27_14835

SSEO:

D0Z67_22095

SBY:	H7H31_04615

SRIM:

CP984_08935 CP984_23685 CP984_38960

SSUB:

CP968_00750 CP968_02880 CP968_15830 CP968_33915

SPHV:

F9278_17975

SCIN:

CP977_27350 CP977_28615

SPAC:

B1H29_00920 B1H29_36145

STSU:

B7R87_00235 B7R87_00255

SCHA:

CP983_09845 CP983_27850

SGX:	H4W23_30995

SCOE:

CP976_22215 CP976_30025 CP976_32365

SBAT:

G4Z16_00070

SNF:	JYK04_00153 JYK04_01859

SPLA:

CP981_29465 CP981_30955 CP981_35585

STUI:

GCM10017668_35390(mmfL) GCM10017668_35620

SATA:

C5746_12505

SCHF:

IPT68_15530 IPT68_28530 IPT68_29305

SHUN:

DWB77_00550 DWB77_04718

SHAR:

HUT13_05645

SCYG:

S1361_31310

SFEU:

IM697_07635 IM697_32675

SLIA:

HA039_01285 HA039_05325 HA039_14005 HA039_29945

SDW:	K7C20_10825 K7C20_28250 K7C20_34355

SCAL:

I6J39_00530 I6J39_15520

SAUH:

SU9_026870 SU9_030680 SU9_031850 SU9_032980

SFB:	CP974_28860

SROI:

IAG44_08745 IAG44_35000

SXN:	IAG42_22440

SGJ:	IAG43_25740 IAG43_33485

SHK:	J2N69_15050 J2N69_24035

SANU:

K7396_00440 K7396_02020 K7396_07590 K7396_08770

STRY:

EQG64_15560

SDD:	D9753_06795 D9753_09135

SACT:

DMT42_11890 DMT42_14060 DMT42_19780 DMT42_29840

SMAO:

CAG99_00900

SINE:

KI385_40060

SDEC:

L3078_43220

SAOV:

G3H79_22390

SYAN:

NRK68_34925

SAKB:

K1J60_19015 K1J60_44780

STAA:

LDH80_09315

SNIG:

HEK616_39440 HEK616_50970

SSPN:

LXH13_23620 LXH13_30520

SCIR:

STRCI_004204 STRCI_006306

SXT:	KPP03845_300021

SLON:

LGI35_17500 LGI35_23850 LGI35_23895

SDRZ:

NEH16_22700 NEH16_31525 NEH16_31970 NEH16_32560

STUD:

STRTU_000345 STRTU_001581 STRTU_007117

SENG:

OJ254_24765 OJ254_30330

SGK:	PET44_33790 PET44_34005 PET44_34835

SANT:

QR300_06555

SYUN:

MOV08_00435 MOV08_05540 MOV08_06650 MOV08_43530

SARG:

HKX69_17125

SJN:	RI060_08575 RI060_20740

SCYN:

N8I84_14930 N8I84_31960

SOV:	QZH56_09430 QZH56_16815

SFIY:

F0344_18560 F0344_34650 F0344_34840

SHAU:

K9S39_02735

SKG:	KJK29_13055 KJK29_13160 KJK29_13465 KJK29_18465

SCOA:

QU709_08700 QU709_09100

SLAI:

P8A22_27830

SROC:

RGF97_13695

SFP:	QUY26_00290 QUY26_19155 QUY26_20885

SCHG:

NRO40_22940

STTN:

BSL84_17800

SINN:

ABB07_25600 ABB07_37440 ABB07_38890

STRZ:

OYE22_02930 OYE22_04425

KBU:	Q4V64_10435 Q4V64_40370

SLUO:

PS467_05255 PS467_07900

STPB:

QR97_23350

SRPA:

HEP86_02845 HEP86_30635 HEP86_37690

SMIB:

SMIR_18380

SCAJ:

O1G22_12240 O1G22_27415 O1G22_43375

STRL:

HEP84_26720 HEP84_55135

STSD:

HEP87_17780 HEP87_27690 HEP87_54015

SRPZ:

HEP85_00935 HEP85_21105

SCHE:

QRN89_26410

SGLY:

P8A20_18785 P8A20_28340

SCAT:

P8A18_17250 P8A18_33385 P8A18_33965

STII:

DRB96_10895 DRB96_12500 DRB96_16040 DRB96_19535

STIC:

DRB89_06045 DRB89_06065 DRB89_13175 DRB89_24345

SABD:

N8I86_01135 N8I86_30170

SCT:	SCAT_0001 SCAT_2185(afsA) SCAT_5778 SCAT_p0948

SCY:	SCATT_21660 SCATT_57810 SCATT_p07910

KSK:	KSE_01060t(ksbS2L) KSE_08560 KSE_22970(ksbS3) KSE_44600(ksbS4) KSE_58120 KSE_75680t(ksbS2R)

KAB:	B7C62_00290

KAU:	B6264_02795 B6264_13770 B6264_20890

KIT:	CFP65_3606 CFP65_4017

KIS:	HUT16_21005

KCH:	O1G21_22250

STRI:

C7M71_001450 C7M71_007220

STRH:

GXP74_01210 GXP74_06785 GXP74_19350 GXP74_38570

AREV:

RVR_3973

RIA:	C7V51_14130

ASOI:

MTP13_02140

ALAV:

MTO99_11590

AGX:	AGREI_0437

ARR:	ARUE_c35120

AWW:	G8758_06600

AAU:

AAur_3376

PAGO:

IRJ34_17125

RDN:	HMPREF0733_10613

BCAU:

I6G59_16805

NDA:

Ndas_3370

NGV:	CDO52_02955

NEX:	NE857_20455

NAKE:

KGD83_08230

NCG:	KGD84_11165

SNAH:

OUQ99_07015 OUQ99_10120

NGN:	LCN96_20855

NFS:	OIE67_15245

MHAI:

OHB01_25095

FRA:	Francci3_2120

BSD:	BLASA_0744

BMON:

ABDB74_03185

SACG:

FDZ84_25550

AMYC:

CU254_30050

AAB:	A4R43_32240

AMYY:

YIM_46150

ARHD:

VSH64_26350 VSH64_43870

AMOG:

QRX60_03825

ACYN:

ORV05_09435

AMYD:

K1T34_06985

SSYI:

EKG83_10415

KAL:

KALB_5811

KUT:	JJ691_07420 JJ691_08030 JJ691_18280

AHM:	TL08_24095

CROS:

N8J89_39685

UME:	RM788_45915

STP:	Strop_4151

SAQ:

Sare_3017

MSAG:

GCM10017556_32740

ACTN:

L083_0231

PRY:	Prubr_43810

DACT:

KZZ52_46345

ALIL:

D5R93_00295

AEY:	CDG81_10645 CDG81_11415

» show all

Reference

1 [PMID:2492509]

Authors

Horinouchi S, Suzuki H, Nishiyama M, Beppu T

Title

Nucleotide sequence and transcriptional analysis of the Streptomyces griseus gene (afsA) responsible for A-factor biosynthesis.

Journal

J Bacteriol 171:1206-10 (1989)
DOI:10.1128/JB.171.2.1206-1210.1989

Sequence

[sgr:SGR_6889]

Reference

2 [PMID:17277085]

Authors

Kato JY, Funa N, Watanabe H, Ohnishi Y, Horinouchi S

Title

Biosynthesis of gamma-butyrolactone autoregulators that switch on secondary metabolism and morphological development in Streptomyces.

Journal

Proc Natl Acad Sci U S A 104:2378-83 (2007)
DOI:10.1073/pnas.0607472104

Reference

3 [PMID:17464053]

Authors

Hsiao NH, Soding J, Linke D, Lange C, Hertweck C, Wohlleben W, Takano E

Title

ScbA from Streptomyces coelicolor A3(2) has homology to fatty acid synthases and is able to synthesize gamma-butyrolactones.

Journal

Microbiology 153:1394-404 (2007)
DOI:10.1099/mic.0.2006/004432-0

Sequence

[sco:SCO6266]

Reference

4 [PMID:19778967]

Authors

Lee YJ, Kitani S, Nihira T

Title

Null mutation analysis of an afsA-family gene, barX, that is involved in biosynthesis of the {gamma}-butyrolactone autoregulator in Streptomyces virginiae.

Journal

Microbiology 156:206-10 (2010)
DOI:10.1099/mic.0.032003-0

Reference

5 [PMID:20358097]

Authors

Corre C, Haynes SW, Malet N, Song L, Challis GL.

Title

A butenolide intermediate in methylenomycin furan biosynthesis is implied by incorporation of stereospecifically 13C-labelled glycerols.

Journal

Chem Commun (Camb) 46:4079-81 (2010)
DOI:10.1039/c000496k

Reference

6 [PMID:33146163]

Authors

Zhou S, Malet NR, Song L, Corre C, Challis GL.

Title

MmfL catalyses formation of a phosphorylated butenolide intermediate in methylenomycin furan biosynthesis.

Journal

Chem Commun (Camb) 56:14443-14446 (2020)
DOI:10.1039/d0cc05658h

Other DBs

ExplorEnz - The Enzyme Database:

2.3.1.277

IUBMB Enzyme Nomenclature:

2.3.1.277

ExPASy - ENZYME nomenclature database:

2.3.1.277

BRENDA, the Enzyme Database:

2.3.1.277

All links

Chemical substance (7)   
   KEGG COMPOUND (7)   
Chemical reaction (5)   
   KEGG REACTION (3)   
   KEGG RCLASS (2)   
Gene (561)   
   KEGG ORTHOLOGY (1)   
   KEGG GENES (479)   
   KEGG MGENES (81)   
Protein sequence (8)   
   UniProt (4)   
   SWISS-PROT (4)   
Protein domain (3)   
   InterPro (3)   
All databases (584)   

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