KEGG ENZYME: 3.2.1.183

ENZYME: 3.2.1.183

Entry

EC 3.2.1.183 Enzyme

Name

UDP-N-acetylglucosamine 2-epimerase (hydrolysing);
UDP-N-acetylglucosamine 2-epimerase (ambiguous);
GNE (gene name);
siaA (gene name);
neuC (gene name)

Class

Hydrolases;
Glycosylases;
Glycosidases, i.e. enzymes that hydrolyse O- and S-glycosyl compounds

Sysname

UDP-N-acetyl-alpha-D-glucosamine hydrolase (2-epimerising)

Reaction(IUBMB)

UDP-N-acetyl-alpha-D-glucosamine + H2O = N-acetyl-D-mannosamine + UDP [RN:R00414]

Reaction(KEGG)

R00414

Substrate

UDP-N-acetyl-alpha-D-glucosamine [CPD:C00043];
H2O [CPD:C00001]

Product

N-acetyl-D-mannosamine [CPD:C00645];
UDP [CPD:C00015]

Comment

The enzyme is found in mammalian liver, as well as in some pathogenic bacteria including Neisseria meningitidis and Staphylococcus aureus. It catalyses the first step of sialic acid (N-acetylneuraminic acid) biosynthesis. The initial product formed is the alpha anomer, which rapidly mutarotates to a mixture of anomers [2]. The mammalian enzyme is bifunctional and also catalyses EC 2.7.1.60, N-acetylmannosamine kinase.
cf. EC 5.1.3.14, UDP-N-acetylglucosamine 2-epimerase (non-hydrolysing).

History

EC 3.2.1.183 created 2012

Pathway

ec00520

Amino sugar and nucleotide sugar metabolism

Orthology

K08068

UDP-N-acetylglucosamine 2-epimerase (hydrolysing)

K12409

bifunctional UDP-N-acetylglucosamine 2-epimerase / N-acetylmannosamine kinase

Genes

HSA:	10020(GNE)

PTR:	465094(GNE)

PPS:	100967642(GNE)

GGO:	101152306(GNE)

PON:	100171416(GNE)

NLE:	100589824(GNE)

MCC:	693525(GNE)

MCF:	102125411(GNE)

CSAB:

103219192(GNE)

RRO:	104667504(GNE)

RBB:	108542566(GNE)

CJC:	100414213(GNE)

SBQ:	101043530(GNE)

MMU:	50798(Gne)

MCAL:

110292565(Gne)

MPAH:

110338653(Gne)

RNO:	114711(Gne)

MUN:	110553818(Gne)

CGE:	100689450(Gne)

NGI:	103745730(Gne)

HGL:	101705910(Gne)

CCAN:

109686839(Gne)

OCU:	100340455(GNE)

TUP:	102487203(GNE)

CFA:	481607(GNE)

VVP:	112930761(GNE)

AML:	100481169(GNE)

UMR:	103678471(GNE)

UAH:	113260452(GNE)

ORO:	101365550(GNE)

ELK:

111145613

FCA:	101098411(GNE)

PTG:	102970000(GNE)

PPAD:

109270143(GNE)

AJU:	106981290(GNE)

BTA:	782201(GNE)

BOM:	102283832(GNE)

BIU:	109563033(GNE)

BBUB:

102389724(GNE)

CHX:	102185360(GNE)

OAS:	101110735(GNE)

SSC:	641344(GNE)

CFR:	102519815(GNE)

CDK:	105102271(GNE)

BACU:

103005913(GNE)

LVE:	103091290(GNE)

OOR:	101276513(GNE)

DLE:	111188102(GNE)

PCAD:

102992566(GNE)

ECB:	100067216(GNE)

EPZ:	103564407(GNE)

EAI:	106826848(GNE)

MYB:	102260594(GNE)

MYD:	102758800(GNE)

MNA:	107544913(GNE)

HAI:	109393773(GNE)

DRO:	112304599(GNE)

PALE:

102889987(GNE)

RAY:	107502823(GNE)

MJV:	108404984(GNE)

LAV:	100654579(GNE)

TMU:

101346980

MDO:	100017383(GNE)

SHR:	100922969(GNE)

PCW:	110220552(GNE)

OAA:	100075502(GNE)

GGA:	427285(GNE)

MGP:	100541275(GNE)

CJO:	107306391(GNE)

NMEL:

110389421(GNE)

APLA:

101793177(GNE)

ACYG:

106046482(GNE)

TGU:	100226686(GNE)

LSR:	110472305(GNE)

SCAN:

103821219(GNE)

GFR:	102037239(GNE)

FAB:	101817440(GNE)

PHI:	102107864(GNE)

PMAJ:

107216215(GNE)

CCAE:

111940925(GNE)

CCW:	104689767(GNE)

ETL:	114056940(GNE)

FPG:	101922061(GNE)

FCH:	102054128(GNE)

CLV:	102088553(GNE)

EGZ:	104122509(GNE)

NNI:	104014062(GNE)

ACUN:

113489984(GNE)

PADL:

103923237(GNE)

AAM:	106487477(GNE)

ASN:	102386832(GNE)

AMJ:	102560703(GNE)

PSS:	102453785(GNE)

CMY:	102934295(GNE)

CPIC:

101938688(GNE)

ACS:	100554566(gne)

PVT:	110070094 110077833(GNE)

PBI:	103050956(GNE)

PMUR:

107293128(GNE)

TSR:	106556779(GNE)

PMUA:

114587739(GNE)

GJA:	107122993(GNE)

XLA:	108703722(gne.S) 108713394(gne.L)

XTR:	780185(gne)

NPR:	108783774(GNE)

DRE:	393857(gne)

SRX:	107723184 107758846

SANH:

107665959 107692604

SGH:	107557951 107576137

CCAR:

109090612(gne)

IPU:	108260684(gne)

PHYP:

113525058(gne)

AMEX:

103023045(gne)

EEE:	113568449(gne)

TRU:	778010(gne)

TNG:	GSTEN00033530G001

LCO:	109138649(gne)

MZE:	101481972(gne)

ONL:	100694518(gne)

OLA:	101166451(gne)

XMA:	102234197(gne)

XCO:	114144860(gne)

PRET:

103468187(gne)

CVG:	107083439(gne)

NFU:	107390962(gne)

KMR:	108241497(gne)

ALIM:

106528332(gne)

AOCE:

111575015(gne)

CSEM:

103384128(gne)

POV:	109627674(gne)

LCF:	108885364(gne)

SDU:	111229391(gne)

SLAL:

111659712(gne)

HCQ:	109519805(gne)

BPEC:

110166180(gne)

MALB:

109970705(gne)

SASA:

106602595 106609886

OTW:	112231842 112245000 112261355

SALP:

111971595 112068287

ELS:	105022904(gne)

SFM:	108938829(gne)

PKI:	111835493(gne)

LCM:	102354276(GNE)

CMK:	103177634(gne)

RTP:	109919025(gne)

BFO:	BRAFLDRAFT_124939 BRAFLDRAFT_210453

SPU:

590539

APLC:

110979892

SKO:

100367992

MIS:	MICPUN_64942

LEZ:

GLE_2255

LEM:

LEN_2779

VOW:	A9237_07150

VNL:	D3H41_01130(neuC)

MBOI:

DQF64_00680(neuC)

ILO:	IL0520(siaA)

ILI:	K734_02605

COZ:	A3Q34_06160

MVS:

MVIS_3781

CEG:	D0C16_04760(neuC)

MMT:	Metme_1161

NME:	NMB0070(synX)

NMP:

NMBB_0074

NMH:	NMBH4476_0070

NMD:	NMBG2136_0073

NMM:	NMBM01240149_0069

NMS:	NMBM01240355_0072

NMQ:	NMBM04240196_0080(siaA)

NMZ:	NMBNZ0533_0076(siaA)

NMA:

NMA0199

NMW:	NMAA_1899(sacA)

NMC:	NMC0054(sacA)

NMN:	NMCC_0078(synX)

NMT:	NMV_0071(siaA)

NWE:	SAMEA3174300_1368(synX)

RSO:	RSp0510(epsC2)

RSL:	RPSI07_mp0439(wecB)

RSN:	RSPO_m00345(epsC2)

RSM:	CMR15_mp10486(wecB)

RSE:

F504_3859

RSY:	RSUY_37590(wecB_1)

RPI:

Rpic_4693

RPF:	Rpic12D_3616

RPJ:	N234_18140 N234_26955

RMN:	TK49_17660

RIN:	ACS15_4961

RPU:	CDC45_20170

CNC:	CNE_1c29640(wecB2)

CPAU:

EHF44_14985

COX:	E0W60_19015

BPS:	BPSS2016(wecB)

BPM:	BURPS1710b_A1131

BPL:	BURPS1106A_A2748

BPD:	BURPS668_A2901

BPSE:

BPSM:

BPSU:

BPSD:

BPZ:	BP1026B_II2167(wecB)

BPQ:	BPC006_II2712

BPK:

BPSH:

BPSA:

BPSO:

BUT:

BTE:	BTH_II0340(wecB)

BTQ:

BTJ:

BTZ:

BTD:

BTV:

BTHE:

BTHM:

BTHA:

BTHL:

BOK:

BOC:

BUU:	WS70_27545

BVI:	Bcep1808_3862 Bcep1808_4142

BVE:	AK36_4552 AK36_4850

BUR:	Bcep18194_A4466

BCN:

Bcen_0854

BCH:	Bcen2424_1335

BCM:	Bcenmc03_1316

BCJ:	BCAL1328(wecB)

BCEW:

DM40_3755

BCEO:

I35_1223(wecB)

BAM:

Bamb_5473

BAC:	BamMC406_3620

BCT:

BCED:

BCEP:

BDL:

BPYR:

BCON:

BUB:	BW23_1692 BW23_5260

BDF:	WI26_17515

BLAT:

BTEI:

BSEM:

BMEC:

BSTG:

BUK:

BUL:

BUD:	AQ610_30580

BPSI:

IX83_06865

HYR:	BSY239_2564(neuC)

HHQ:	HPSH169_04330

HHR:	HPSH417_04100

HPT:	HPSAT_02530

HEP:	HPPN120_04180

HEU:	HPPN135_04160

HPYK:

HPAKL86_02820

HAC:	Hac_1270(neuC)

HMS:

HMU06150

HFE:	HFELIS_02730

HBI:	HBZC1_02540

HCE:

HCW_07300

HCM:

HCD_01690

HBL:	XJ32_01825

HET:	BBW65_04555

SULG:

FJR48_00815(neuC)

CJE:	Cj1142(neuC1)

CJB:	BN148_1142(neuC1)

CJJ:	CJJ81176_1159

CJU:

C8J_1338

CJI:	CJSA_1084(neuC1)

CJP:	A911_05535

CJEJ:

CJEU:

CJEN:

CJEI:

CJY:	QZ67_01220(siaA)

CJL:	PJ17_05845

CJW:	PJ18_05660

CJZ:	M635_01410

CCOL:

BN865_09880c

CCY:	YSS_06170 YSS_07640

CIS:	CINS_1204(neuC)

CSM:	CSUB8521_1426(neuC)

CAVI:

CAV_0274(neuC)

CHW:	A2J15_001220(neuC)

ABL:	A7H1H_1747

SBA:	Sulba_1895

DVM:	DvMF_1846 DvMF_2638

DDE:

Dde_3255

DHY:	DESAM_21180

DPI:

BN4_12681

DSF:	UWK_02428 UWK_03119

SMER:

DU99_30360

SIX:	BSY16_2626(neuC)

SAME:

SAMCFNEI73_pC1684

REI:	IE4771_CH00808

MET:

M446_3311

MNO:

Mnod_2549

RCP:	RCAP_rcc02964(webC)

RBL:	B6K69_05250

OTM:	OSB_23420(siaA)

OCT:	FTO60_12830(neuC)

PTP:	RCA23_c08960(wecB)

PPHR:

APZ00_22690

DON:	BSK21_04545

LVS:	LOKVESSMR4R_00716(siaA)

TAW:	EI545_04040(neuC)

HML:	HmaOT1_13645(neuC)

PSEB:

EOK75_02950(neuC)

RBZ:	B9057_08950

FER:	FNB15_03015(neuC) FNB15_03035(neuC)

ECOG:

FIV45_02380(neuC)

OCN:	CUC15_16535(neuC)

LPAK:

GDS87_03425(neuC)

SIV:

SSIL_3275

HHW:	NCTC503_01054(neuC)

PSOR:

RSJ16_13960

COB:	COB47_0922

TUR:	AT726_03455

GOB:

Gobs_4333

PSUF:

A1sIA56_00120

AYM:	YM304_30300(neuC)

SYNW:

SynWH8103_00492(neuC)

PME:	NATL1_08731

ASX:	CDL62_03675(neuC)

ALM:	AO498_13970

DFE:

Dfer_3364

NIB:	GU926_17080(neuC)

GRS:	C7S20_00250(neuC)

FPS:	FP1255(neuC)

FPC:	FPSM_02166

FPY:	FPG101_10855

FPO:	FPG3_03205

FPQ:	IB65_05910

FPV:	IA03_06015

FPW:	IA04_05920

FPK:	IA06_05955

FJO:

Fjoh_0304

FIN:	KQS_03400(neuC)

FKI:	FK004_09135

LAN:	Lacal_0113

LVN:	BWR22_10525

LACI:

CW733_07990(neuC)

POLA:

BXQ17_03860

POA:	CW731_03485(neuC)

WIN:

WPG_0169

WIJ:	BWZ20_04180

AHZ:	APS56_05275

TEN:	LPB136_04680

LUL:	LPB138_01920

WFU:	AXE80_08445

FOP:	FNB79_09375(neuC)

SALT:

AO058_07930

OAQ:	DZC78_14810(neuC)

FEK:	C1H87_05355(neuC)

KAN:	IMCC3317_05780

MARF:

CJ739_164

PSYN:

E9099_01275(neuC)

AFLA:

FHG64_14700(neuC)

BBAU:

AEM51_03765

PROC:

Ptc2401_00367(siaA)

TAH:	SU86_007045

» show all

Reference

1 [PMID:9305888]

Authors

Stasche R, Hinderlich S, Weise C, Effertz K, Lucka L, Moormann P, Reutter W

Title

A bifunctional enzyme catalyzes the first two steps in N-acetylneuraminic acid biosynthesis of rat liver. Molecular cloning and functional expression of UDP-N-acetyl-glucosamine 2-epimerase/N-acetylmannosamine kinase.

Journal

J Biol Chem 272:24319-24 (1997)
DOI:10.1074/jbc.272.39.24319

Sequence

[rno:114711]

Reference

2 [PMID:12603133]

Authors

Chou WK, Hinderlich S, Reutter W, Tanner ME

Title

Sialic acid biosynthesis: stereochemistry and mechanism of the reaction catalyzed by the mammalian UDP-N-acetylglucosamine 2-epimerase.

Journal

J Am Chem Soc 125:2455-61 (2003)
DOI:10.1021/ja021309g

Reference

3 [PMID:15135418]

Authors

Blume A, Ghaderi D, Liebich V, Hinderlich S, Donner P, Reutter W, Lucka L

Title

UDP-N-acetylglucosamine 2-epimerase/N-acetylmannosamine kinase, functionally expressed in and purified from Escherichia coli, yeast, and insect cells.

Journal

Protein Expr Purif 35:387-96 (2004)
DOI:10.1016/j.pep.2004.02.013

Reference

4 [PMID:15518580]

Authors

Murkin AS, Chou WK, Wakarchuk WW, Tanner ME

Title

Identification and mechanism of a bacterial hydrolyzing UDP-N-acetylglucosamine 2-epimerase.

Journal

Biochemistry 43:14290-8 (2004)
DOI:10.1021/bi048606d

Sequence

[nme:NMB0070]