KEGG ENZYME: 4.2.1.159

ENZYME: 4.2.1.159

Entry

EC 4.2.1.159                Enzyme

Name

dTDP-4-dehydro-6-deoxy-alpha-D-glucopyranose 2,3-dehydratase;
jadO (gene name);
evaA (gene name);
megBVI (gene name);
eryBV (gene name);
mtmV (gene name);
oleV (gene name);
spnO (gene name);
TDP-4-keto-6-deoxy-D-glucose 2,3-dehydratase;
dTDP-4-dehydro-6-deoxy-alpha-D-glucopyranose hydro-lyase (dTDP-(2R,6S)-2,4-dihydroxy-6-methyl-2,6-dihydropyran-3-one-forming)

Class

Lyases;
Carbon-oxygen lyases;
Hydro-lyases

Sysname

dTDP-4-dehydro-6-deoxy-alpha-D-glucopyranose hydro-lyase (dTDP-2,6-dideoxy-D-glycero-hex-2-enos-4-ulose-forming)

Reaction(IUBMB)

dTDP-4-dehydro-6-deoxy-alpha-D-glucopyranose = dTDP-3,4-didehydro-2,6-dideoxy-alpha-D-glucose + H2O (overall reaction) [RN:R05518];
(1a) dTDP-4-dehydro-6-deoxy-alpha-D-glucopyranose = dTDP-2,6-dideoxy-D-glycero-hex-2-enos-4-ulose + H2O [RN:R06428];
(1b) dTDP-2,6-dideoxy-D-glycero-hex-2-enos-4-ulose = dTDP-3,4-didehydro-2,6-dideoxy-alpha-D-glucose (spontaneous) [RN:R11034]

Reaction(KEGG)

R05518 R06428 R11034

Substrate

dTDP-4-dehydro-6-deoxy-alpha-D-glucopyranose [CPD:C11907];
dTDP-2,6-dideoxy-D-glycero-hex-2-enos-4-ulose [CPD:C11930]

Product

dTDP-3,4-didehydro-2,6-dideoxy-alpha-D-glucose [CPD:C06620];
H2O [CPD:C00001];
dTDP-2,6-dideoxy-D-glycero-hex-2-enos-4-ulose [CPD:C11930]

Comment

The enzyme participates in the biosynthesis of several deoxysugars, including beta-L-4-epi-vancosamine, alpha-L-megosamine, L- and D-olivose, D-oliose, D-mycarose, forosamine and beta-L-digitoxose. In vitro the intermediate can undergo a spontaneous decomposition to maltol [2,3].

History

EC 4.2.1.159 created 2015

Pathway

ec00523

Polyketide sugar unit biosynthesis

ec01055

Biosynthesis of vancomycin group antibiotics

ec01100

Metabolic pathways

ec01110

Biosynthesis of secondary metabolites

Orthology

K16435

dTDP-4-dehydro-6-deoxy-alpha-D-glucopyranose 2,3-dehydratase

Genes

VCX:	VAA049_3444

SDE:

Sde_2127

TLR:	Thiosp_04676

REV:	HUE57_13920

AMON:

H9L24_02340

HTN:	KI616_09480

HOE:	IMCC20628_04711

BGZ:	XH91_11595

BROS:

QUH67_25975

MMR:	Mmar10_0545

SHUM:

STHU_14710

TMK:	QGN29_06855

GSO:	PH603_08930

GEM:

GM21_0940

GUR:

Gura_4278

GEO:

Geob_0428

GBM:

Gbem_3308

GBN:	GEOBRER4_09090

DMA:

DMR_07580

DCB:	C3Y92_16665

DSA:	Desal_3612

LYG:	C1N55_04675

LLF:	BCR17_06565

WDI:	H9L19_07475

DOR:	Desor_5131

DMI:	Desmer_4107

LBW:	C3V36_01190

LCG:	L3BBH23_23160

AHQ:	NMU03_10395

CIU:	G4D55_18805

NBR:	O3I_007495 O3I_015250

NTP:	CRH09_07965 CRH09_20630

NWL:	NWFMUON74_25900

NIE:	KV110_14290 KV110_35800

TPR:

Tpau_3481

DPC:	A6048_11420

SALB:

XNR_0600

SMA:	SAVERM_950(aveBVI)

SGR:

SGR_633

SFI:

SFUL_5272

SANL:

KZO11_24435 KZO11_29550

SGRF:

SGFS_016250

SCYE:

R2B67_24830

SCB:	SCAB_83991

SVL:	Strvi_3809

SRC:	M271_00405 M271_06420

SMAL:

SMALA_7128

SSOI:

I1A49_39420

SBH:	SBI_01545 SBI_06874

SVE:

SVEN_5994

SDV:	BN159_2519

SALS:

SLNWT_0705 SLNWT_7313

SCI:	B446_13490

SVT:	SVTN_18805

STRE:

GZL_01620

SLD:

T261_6842

SLC:	SL103_12590

SXI:	SXIM_35760

SAMB:

SAM23877_5618(srm19)

SPRI:

SPRI_0250 SPRI_7103

SCX:	AS200_01290

SRW:	TUE45_01318

SLE:	sle_09630(sle_09630)

SRN:	A4G23_02281

SPAV:

Spa2297_32825

SCLF:

BB341_29660

SGS:	AVL59_46210

SALW:

CP975_00340

SGM:	GCM10017557_01740 GCM10017557_73700

SCAD:

DN051_13660

SPHW:

NFX46_24940

SNR:	SNOUR_06865 SNOUR_10090(eryBVI)

SALU:

DC74_6604

SALL:

SAZ_34335

SNW:	BBN63_25020

SAUO:

BV401_39270

SVU:	B1H20_22670 B1H20_29860

SPUN:

BFF78_11180

SALF:

SMD44_08278

SALJ:

SMD11_1662

SLX:	SLAV_40175

STRO:

STRMOE7_07500

SFK:

KY5_2324

SLK:	SLUN_13805

SDX:	C4B68_09680

SGD:	ELQ87_00890 ELQ87_08060

SNQ:	CP978_29670

STIR:

DDW44_27815

SKA:	CP970_30865 CP970_39800

SRK:	FGW37_16325

SFIC:

EIZ62_04075 EIZ62_09585

SGAL:

CP966_29035

SSPO:

DDQ41_30680

SPAD:

DVK44_01735

SGF:	HEP81_07930

SCAV:

CVT27_24440

SRIM:

CP984_10770

SPHV:

F9278_28220

SCIN:

CP977_28090

SPAC:

B1H29_00715 B1H29_36345

STSU:

B7R87_22130

SCHA:

CP983_27975

SCOE:

CP976_32945

SBRO:

GQF42_07475

SCHF:

IPT68_29240

SHUN:

DWB77_05139

SHAR:

HUT13_24970

SCYG:

S1361_05000 S1361_29920

SFEU:

IM697_37735

SLIA:

HA039_05635

SDW:	K7C20_32610

SCAL:

I6J39_29665

SAUH:

SU9_032835

SFB:	CP974_12555

SMOB:

J7W19_17605 J7W19_28800

SPEU:

CGZ69_24345

SXN:	IAG42_36010

SGJ:	IAG43_33090

SHK:	J2N69_28810

SANU:

K7396_04485 K7396_33455

SDD:	D9753_11220

SMAO:

CAG99_12095

SGOB:

test1122_15665

SINE:

KI385_25275

SLF:	JEQ17_40470

SDEC:

L3078_20655

SRUG:

F0345_27430

SAKB:

K1J60_45150

STAA:

LDH80_09650

SNIG:

HEK616_47320

SCAE:

IHE65_08890

STUB:

MMF93_33240

SSPN:

LXH13_14100

SCIR:

STRCI_006074

STUD:

STRTU_005105 STRTU_006735

SANT:

QR300_05440

SYUN:

MOV08_06780

SJN:	RI060_04580 RI060_18315

SHAU:

K9S39_40785

SKG:	KJK29_16115

SLAI:

P8A22_08980

SFP:	QUY26_02160

SCHG:

NRO40_12710

STTN:

BSL84_24975

KAB:	B7C62_31105

KIS:	HUT16_23825

STRI:

C7M71_025695 C7M71_025875

YIA:	LO772_07335

ABRY:

NYE86_15410 NYE86_16010

MHUM:

NNL39_09870

MDB:	OVN18_02325

ARUB:

J5A65_00460

AER:	AERYTH_15845

TALX:

FOF52_07490 FOF52_14775

NDA:

Ndas_4708

NAL:

B005_1432

NGV:	CDO52_02795

NFE:	HUT17_04685

NAKE:

KGD83_01615

NCG:	KGD84_13375

STRR:

EKD16_15560

SNAH:

OUQ99_30535

TCU:

Tcur_2760

ACTW:

F7P10_30175 F7P10_30200

AGRA:

AGRA3207_007759

AMAZ:

LUW76_46780

SPIQ:

OHA34_04030

ACTQ:

OG417_42860 OG417_42875

NOW:	GBF35_40110

NCX:	Nocox_25610

FRA:	Francci3_4134

SEN:	SACE_0717(eryBVI)

SACG:

FDZ84_24205

SVI:	Svir_29870

SACC:

EYD13_16500

AMD:	AMED_0645 AMED_5402

AMN:	RAM_03295 RAM_27540

AMM:	AMES_0643 AMES_5337

AMZ:	B737_0644 B737_5337

AOI:

AORI_1498

AJA:	AJAP_32030

AMYC:

CU254_17440

AMYB:

BKN51_41530

AAB:	A4R43_01810

AMYY:

YIM_08355 YIM_11645 YIM_22855

AORI:

SD37_33630 SD37_34285

APRT:

MUY14_22470

AROO:

NQK81_15400

PSEH:

XF36_05045

PSEQ:

AD006_29960

PECQ:

AD017_31290

PHH:	AFB00_29740(selSVII)

SESP:

BN6_58920(sam31)

SSYI:

EKG83_32265

KAL:	KALB_6582(acuS4)

KUT:	JJ691_101510 JJ691_70330

KPHY:

AOZ06_22485 AOZ06_23375

LED:	BBK82_43750

AHM:	TL08_05635 TL08_15940

ACTI:

UA75_05675 UA75_16845

ACAD:

UA74_05670

AHG:	AHOG_05435 AHOG_15160 AHOG_15195

ACTA:

C1701_01560 C1701_26015

ALO:

CRK56087

PMAD:

BAY61_07755

ACTU:

Actkin_00393 Actkin_02428(perS10)

CROS:

N8J89_20360 N8J89_26400

STP:	Strop_2181

SAQ:	Sare_1267 Sare_2340

MAU:	Micau_3987

MIL:

ML5_4434

MICB:

MicB006_4920

MCAB:

HXZ27_04100(evdS9)

MCRA:

ID554_11975 ID554_28100

VER:	HUT12_18885

MENO:

Jiend_53080

MCHL:

PVK74_00245

MFEU:

H1D33_25620

MPRN:

Q3V37_18325

AMS:	AMIS_50580

AOU:	ACTOB_006489

PLK:	CIK06_11040

PSUU:

Psuf_058320 Psuf_058570

DVC:	Dvina_05940 Dvina_31405

DFU:	Dfulv_18280 Dfulv_29145

DROS:

Drose_26850

DAUR:

Daura_30065 Daura_37965

DMAT:

Dmats_05420 Dmats_26500

NHY:	JQS43_06855

CCAZ:

COUCH_16050

AEY:	CDG81_13205

CYI:	CBM981_2305

LKB:	LPTSP3_g21200

EDA:	GWR55_15460

BFR:

BF0809

BFB:	VU15_03400

BCEL:

BcellWH2_00546 BcellWH2_04965

ASX:	CDL62_18260

ALGO:

GYM62_12440

RUF:	TH63_02825

GFO:

GFO_2035

FNK:	E1750_13615

FAN:	GENT5_10180

FBU:	UJ101_00308 UJ101_00547

PROC:

Ptc2401_00807

NBV:

T478_0170

» show all

Reference

1 [PMID:10770761]

Authors

Aguirrezabalaga I, Olano C, Allende N, Rodriguez L, Brana AF, Mendez C, Salas JA

Title

Identification and expression of genes involved in biosynthesis of L-oleandrose and its intermediate L-olivose in the oleandomycin producer Streptomyces antibioticus.

Journal

Antimicrob Agents Chemother 44:1266-75 (2000)
DOI:10.1128/AAC.44.5.1266-1275.2000

Sequence

[ag:AAD55451]

Reference

2 [PMID:11035791]

Authors

Chen H, Thomas MG, Hubbard BK, Losey HC, Walsh CT, Burkart MD.

Title

Deoxysugars in glycopeptide antibiotics: enzymatic synthesis of TDP-L-epivancosamine in chloroeremomycin biosynthesis.

Journal

Proc Natl Acad Sci U S A 97:11942-7 (2000)
DOI:10.1073/pnas.210395097

Reference

3 [PMID:11254130]

Authors

Gonzalez A, Remsing LL, Lombo F, Fernandez MJ, Prado L, Brana AF, Kunzel E, Rohr J, Mendez C, Salas JA

Title

The mtmVUC genes of the mithramycin gene cluster in Streptomyces argillaceus are involved in the biosynthesis of the sugar moieties.

Journal

Mol Gen Genet 264:827-35 (2001)
DOI:10.1007/s004380000372

Sequence

[ag:CAK50786]

Reference

4 [PMID:11932454]

Authors

Wang L, White RL, Vining LC

Title

Biosynthesis of the dideoxysugar component of jadomycin B: genes in the jad cluster of Streptomyces venezuelae ISP5230 for L-digitoxose assembly and transfer to the angucycline aglycone.

Journal

Microbiology 148:1091-103 (2002)
DOI:10.1099/00221287-148-4-1091

Sequence

[ag:AAK01936]

Reference

5 [PMID:18345667]

Authors

Hong L, Zhao Z, Melancon CE 3rd, Zhang H, Liu HW

Title

In vitro characterization of the enzymes involved in TDP-D-forosamine biosynthesis in the spinosyn pathway of Saccharopolyspora spinosa.

Journal

J Am Chem Soc 130:4954-67 (2008)
DOI:10.1021/ja0771383