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

ec00541

O-Antigen nucleotide sugar biosynthesis

ec01100

Metabolic pathways

Orthology

K08068

UDP-N-acetylglucosamine 2-epimerase (hydrolysing)

K12409

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

K24257

UDP-N-acetylglucosamine 2-epimerase (hydrolysing)

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)

MTHB:

126938036

CSAB:

103219192(GNE)

CATY:

105598144(GNE)

PANU:

101010073(GNE)

TGE:	112608700(GNE)

RRO:	104667504(GNE)

RBB:	108542566(GNE)

TFN:	117098986(GNE)

PTEH:

111536746(GNE)

CJC:	100414213(GNE)

SBQ:	101043530(GNE)

CSYR:

103265267(GNE)

MMUR:

105874285(GNE)

LCAT:

123646130(GNE)

OGA:	100967144(GNE)

MMU:	50798(Gne)

MCAL:

110292565(Gne)

MPAH:

110338653(Gne)

RNO:	114711(Gne)

MCOC:

116095921(Gne)

MUN:	110553818(Gne)

CGE:	100689450(Gne)

MAUA:

101825421(Gne)

PLEU:

114710578(Gne)

MORG:

121458301(Gne)

MFOT:

126509927

AAMP:

119825908(Gne)

NGI:	103745730(Gne)

HGL:	101705910(Gne)

CPOC:

100731383(Gne)

CCAN:

109686839(Gne)

DORD:

105993415(Gne)

DSP:	122123822(Gne)

NCAR:

124964247

OCU:	100340455(GNE)

OPI:	101516977(GNE)

TUP:	102487203(GNE)

CFA:	481607(GNE)

CLUD:

112649779(GNE)

VVP:	112930761(GNE)

VLG:	121495297(GNE)

AML:	100481169(GNE)

UMR:	103678471(GNE)

UAH:	113260452(GNE)

UAR:	123781045(GNE)

ELK:

111145613

LLV:

125083210

MPUF:

101692212(GNE)

ORO:	101365550(GNE)

EJU:	114213520(GNE)

ZCA:	113934382(GNE)

MLX:	118017947(GNE)

NSU:	110581892(GNE)

FCA:	101098411(GNE)

PYU:	121034667(GNE)

PBG:	122474871(GNE)

LRUF:

124501832

PTG:	102970000(GNE)

PPAD:

109270143(GNE)

AJU:	106981290(GNE)

HHV:	120233505(GNE)

BTA:	782201(GNE)

BOM:	102283832(GNE)

BIU:	109563033(GNE)

BBUB:

102389724(GNE)

CHX:	102185360(GNE)

OAS:	101110735(GNE)

ODA:	120882680(GNE)

CCAD:

122453287(GNE)

SSC:	641344(GNE)

CFR:	102519815(GNE)

CBAI:

105067351(GNE)

CDK:	105102271(GNE)

VPC:	102537717(GNE)

BACU:

103005913(GNE)

LVE:	103091290(GNE)

OOR:	101276513(GNE)

DLE:	111188102(GNE)

PCAD:

102992566(GNE)

PSIU:

116755092(GNE)

ECB:	100067216(GNE)

EPZ:	103564407(GNE)

EAI:	106826848(GNE)

MYB:	102260594(GNE)

MYD:	102758800(GNE)

MMYO:

118667317(GNE)

MLF:	102419867(GNE)

MNA:	107544913(GNE)

PKL:	118716325(GNE)

HAI:	109393773(GNE)

DRO:	112304599(GNE)

SHON:

118979592(GNE)

AJM:	119048758(GNE)

PDIC:

114494365(GNE)

PHAS:

123819964(GNE)

MMF:	118629733(GNE)

RFQ:	117032175(GNE)

PALE:

102889987(GNE)

PGIG:

120598059(GNE)

PVP:	105296274(GNE)

RAY:	107502823(GNE)

MJV:	108404984(GNE)

TOD:	119232808(GNE)

SARA:

101538698

LAV:	100654579(GNE)

TMU:

101346980

DNM:	101419183(GNE)

MDO:	100017383(GNE)

GAS:	123234985(GNE)

SHR:	100922969(GNE)

PCW:	110220552(GNE)

OAA:	100075502(GNE)

GGA:	427285(GNE)

PCOC:

116240072(GNE)

MGP:	100541275(GNE)

CJO:	107306391(GNE)

NMEL:

110389421(GNE)

APLA:

101793177(GNE)

ACYG:

106046482(GNE)

AFUL:

116501011(GNE)

TGU:	100226686(GNE)

LSR:	110472305(GNE)

SCAN:

103821219(GNE)

PMOA:

120509491(GNE)

OTC:	121334700(GNE)

PRUF:

121355735(GNE)

GFR:	102037239(GNE)

FAB:	101817440(GNE)

PHI:	102107864(GNE)

PMAJ:

107216215(GNE)

CCAE:

111940925(GNE)

CCW:	104689767(GNE)

CBRC:

103616383(GNE)

ETL:	114056940(GNE)

ZAB:	102065100(GNE)

ACHL:

103811099(GNE)

FPG:	101922061(GNE)

FCH:	102054128(GNE)

CLV:	102088553(GNE)

EGZ:	104122509(GNE)

NNI:	104014062(GNE)

PLET:

104620096(GNE)

PCRI:

104024025(GNE)

ACUN:

113489984(GNE)

TALA:

104355506(GNE)

PADL:

103923237(GNE)

AFOR:

103896116(GNE)

ACHC:

115337028(GNE)

HALD:

104311348(GNE)

CCRI:

104158365(GNE)

CSTI:

104564143(GNE)

EHS:	104506085(GNE)

CMAC:

104476212

MUI:	104541040(GNE)

FGA:	104084273(GNE)

GSTE:

104264212(GNE)

LDI:	104347190(GNE)

MNB:	103771013(GNE)

OHA:	104331293(GNE)

NNT:	104413666(GNE)

DPUB:

104304860(GNE)

PGUU:

104457592(GNE)

ACAR:

104525696(GNE)

AVIT:

104278137(GNE)

CVF:	104295332(GNE)

AAM:	106487477(GNE)

AROW:

112968982(GNE)

NPD:	112946271(GNE)

TGT:	104577696(GNE)

DNE:	112982745(GNE)

SCAM:

104151901(GNE)

ASN:	102386832(GNE)

AMJ:	102560703(GNE)

CPOO:

109323548(GNE)

PSS:	102453785(GNE)

CMY:	102934295(GNE)

CPIC:

101938688(GNE)

TST:	117878843(GNE)

CABI:

116832499(GNE)

MRV:	120408152(GNE)

ACS:	100554566(gne)

PVT:	110070094 110077833(GNE)

SUND:

121922067(GNE)

PBI:	103050956(GNE)

PMUR:

107293128(GNE)

CTIG:

120308565(GNE)

TSR:	106556779(GNE)

PGUT:

117661672(GNE)

VKO:	123030193(GNE)

PMUA:

114587739(GNE)

ZVI:	118097722(GNE)

GJA:	107122993(GNE)

STOW:

125436394(GNE)

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

XTR:	780185(gne)

NPR:	108783774(GNE)

RTEM:

120946964(GNE)

BBUF:

120989336(GNE)

BGAR:

122931704(GNE)

DRE:	393857(gne)

SRX:	107723184 107758846

SANH:

107665959 107692604

SGH:	107557951 107576137

CCAR:

109090612(gne)

CAUA:

113044323 113105655

PPRM:

120478304(gne)

MAMB:

125272476(gne)

IPU:	108260684(gne)

PHYP:

113525058(gne)

SMEO:

124381239(gne)

TFD:	113635349(gne)

AMEX:

103023045(gne)

EEE:	113568449(gne)

TRU:	778010(gne)

TNG:	GSTEN00033530G001

LCO:	109138649(gne)

CGOB:

115010192(gne)

ELY:	117255161(gne)

EFO:	125885912(gne)

PLEP:

121941973(gne)

SLUC:

116042885(gne)

ECRA:

117958336(gne)

ESP:	116698211(gne)

PFLV:

114572183(gne)

GAT:	120825172(gne)

PPUG:

119217580(gne)

MSAM:

119899371(gne)

CUD:	121508197(gne) 121508704

ALAT:

119017552(gne)

MZE:	101481972(gne)

ONL:	100694518(gne)

OAU:	116313305(gne)

OLA:	101166451(gne)

OML:	112137366(gne)

XMA:	102234197(gne)

XCO:	114144860(gne)

XHE:	116720160(gne)

PRET:

103468187(gne)

PFOR:

103148745(gne)

PLAI:

106959210(gne)

PMEI:

106905473(gne)

GAF:	122829778(gne)

CVG:	107083439(gne)

CTUL:

119787121(gne)

GMU:	124868010(gne)

NFU:	107390962(gne)

KMR:	108241497(gne)

ALIM:

106528332(gne)

NWH:	119422385(gne)

AOCE:

111575015(gne)

MCEP:

125004295(gne)

CSEM:

103384128(gne)

POV:	109627674(gne)

SSEN:

122760387 122771022(gne)

HHIP:

117769603(gne)

HSP:	118117219(gne)

LCF:

108885364

SDU:	111229391(gne)

SLAL:

111659712(gne)

XGL:	120800274(gne)

HCQ:	109519805(gne)

BPEC:

110166180(gne)

MALB:

109970705(gne)

BSPL:

114852873(gne)

SASA:

106602595 106609886

STRU:

115191847 115202183

OTW:	112231842 112245000

OMY:	110498664 110534456(gne)

OGO:	124001482 124012377(gne)

ONE:

115137365

SALP:

111971595 112068287

SNH:	120034994(gne) 120052903

CCLU:

121535759(gne)

ELS:	105022904(gne)

SFM:	108938829(gne)

PKI:	111835493(gne)

AANG:

118227328(gne) 118231256

LOC:	102687010(gne)

PSPA:

121319312(gne)

ARUT:

117408557 117421398

LCM:	102354276(GNE)

CMK:	103177634(gne)

RTP:	109919025(gne)

BFO:	118413467 118416361

BBEL:

109474908 109478571

SPU:

590539

APLC:

110979892

SKO:

100367992

MIS:	MICPUN_64942

ECOO:

ECRM13514_2760(nnaA)

ECOH:

ECRM13516_2628(nnaA)

ESL:

O3K_09240

ESO:

O3O_16380

ESM:

O3M_09205

ECK:	EC55989_2293

ECV:	APECO1_3473(neuC)

ECM:	EcSMS35_3230(neuC)

ECT:	ECIAI39_3441(neuC)

EOC:	CE10_3479(neuC)

ECI:	UTI89_C3370(neuC)

EIH:	ECOK1_3367(neuC)

ECZ:	ECS88_3328(neuC)

ELU:	UM146_01630

ECOI:

ECOPMV1_03250(neuC)

SBZ:

A464_2220

SBV:	N643_09305

PTT:	VY86_07620

EIC:	NT01EI_1318

ETR:	ETAE_1209(neuC)

ETD:

ETAF_1124

ETE:	ETEE_3153(wecB)

ETC:	ETAC_05755

EDW:	QY76_14230

EDL:	AAZ33_06225(neuC)

EHO:	A9798_10685

LRI:	NCTC12151_01028(neuC)

HPR:	PARA_02830(nnaA)

MHT:	D648_18120(neuC)

MHQ:	D650_8040(neuC)

MHAT:

B824_18200(neuC)

MHX:	MHH_c26650(nnaA)

MHAE:

F382_04080

MHAM:

J450_03110

MHAO:

J451_04320

MHAL:

N220_10180

MHAQ:

WC39_04025

MHAY:

VK67_04025

MVR:

X781_6010

MVI:	X808_15550

MVG:	X874_14490

MVE:

X875_5530

MGRA:

A4G16_01270

MBOS:

ICJ55_05345(neuC)

ASI:	ASU2_01195 ASU2_10555

ASS:	ASU1_01200

AEU:	ACEE_01055

ADP:	NCTC12871_01318(neuC)

APAG:

EIA51_04600(neuC)

RPNE:

NCTC8284_01160(neuC_1)

RHEY:

FEE42_11170(neuC)

VOW:	A9237_07150

VNL:	D3H41_01130(neuC)

VSA:	VSAL_I3013(neuC)

PGB:	H744_2c2920

MBOI:

DQF64_00680(neuC)

SBK:	SHEWBE_0695(siaA)

ILO:	IL0520(siaA)

ILI:	K734_02605

FES:	HER31_10790(neuC)

MVS:

MVIS_3781

CEG:	D0C16_04760(neuC)

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)

NMC:	NMC0054(sacA)

NMN:	NMCC_0078(synX)

NMT:	NMV_0071(siaA)

NWE:	SAMEA3174300_1368(synX)

NBL:	GJV52_06955(neuC)

SMUR:

BWP33_01875

RPJ:	N234_26955

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)

HFE:	HFELIS_02730

HBI:	HBZC1_02540

HCE:

HCW_07300

HCM:

HCD_01690

HBL:	XJ32_01825

HET:	BBW65_04555

HCL:	NCTC13205_00837(neuC)

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:

N564_01108

CJEU:

N565_01151

CJEN:

N755_01146

CJEI:

N135_01179

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)

CUX:	CUP3940_0881(neuC)

CBLA:

CBLAS_1485(neuC)

CMUC:

CMCT_1131(neuC)

CNV:	CNZW441b_1142(neuC)

SBA:	Sulba_1895

ABL:	A7H1H_1747

ALK:

ALEK_0979

GSUB:

KP001_18460(neuC)

GPL:	M1B72_01990(neuC)

DVM:

DvMF_1846

DDE:

Dde_3255

DHY:	DESAM_21180

DSF:

UWK_03119

DBK:	DGMP_13670(neuC)

SMER:

DU99_30360

SIX:	BSY16_2626(neuC)

SAME:

SAMCFNEI73_pC1684

PPHR:

APZ00_22690

OTM:	OSB_23420(siaA)

OCT:	FTO60_12830(neuC)

RCP:	RCAP_rcc02964(webC)

RBL:	B6K69_05250

PTP:	RCA23_c08960(wecB)

DON:	BSK21_04545

LVS:	LOKVESSMR4R_00716(siaA)

TAW:	EI545_04040(neuC)

HML:	HmaOT1_13645(neuC)

PSEB:

EOK75_02950(neuC)

PAMO:

BAR1_13860(neuC)

RBZ:	B9057_08950

ECOG:

FIV45_02380(neuC)

OCN:	CUC15_16535(neuC)

LPAK:

GDS87_03425(neuC)

BVJ:	I5776_04790(neuC)

SIV:

SSIL_3275

SAG:	SAG1160(neuC)

SAN:

neuC

SAK:	SAK_1249(neuC)

SGC:	A964_1133(wecB)

SAGS:

SaSA20_0982(neuC)

SAGL:

GBS222_0992(neuC)

SAGM:

BSA_12380

SAGI:

MSA_12800

SAGR:

SAIL_12800

SAGP:

V193_05420

SAGC:

DN94_05420

SAGT:

GBSCOH1_1066

SAGE:

EN72_06450

SAGG:

EN73_05985

SAGN:

W903_1243(neuC)

SSB:	SSUBM407_1279(neuC)

SSU:	SSU05_0579

SSV:	SSU98_0583

SSI:	SSU0536(neuC)

SSS:	SSUSC84_0518(neuC)

SSF:	SSUA7_0539

SSW:	SSGZ1_0572

SUP:

YYK_02540

SSUS:

NJAUSS_0544

SUI:	SSUJS14_0543

SUO:	SSU12_0540

SRP:	SSUST1_1226

SSUT:

TL13_1187(neuC)

SSUI:

T15_1400(wecB)

SRQ:	SR187_6420

AUH:	AWM75_07810

HHW:	NCTC503_01054(neuC)

RGN:	RGna_11995(neuC)

SINT:

K5I26_06375(neuC)

PSOR:

RSJ16_13960

COB:	COB47_0922

TUR:	AT726_03455

NPC:	KUV85_15590(neuC)

GOB:

Gobs_4333

PSUF:

A1sIA56_00120

AYM:	YM304_30300(neuC)

SYNW:

SynWH8103_00492(neuC)

PME:	NATL1_08731

FNT:	HMPREF0405_00113

FVA:	FV113G1_31680

PBY:	L6471_06310(neuC)

AIT:	AI2BBH_P060(neuC)

ASX:	CDL62_03675(neuC)

ALM:	AO498_13970

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

FKI:	FK004_09135

FSN:	GS03_01395(siaA)

FFL:	HYN86_01535(neuC)

FSD:	LXD69_00560(neuC)

FCB:	LOS89_02805(neuC)

FPB:	NLJ00_01820(neuC)

LAN:	Lacal_0113

LACI:

CW733_07990(neuC)

POLA:

BXQ17_03860

POA:	CW731_03485(neuC)

PPEC:

H9W90_03850(neuC)

PUN:	NQP51_04910(neuC)

WIN:

WPG_0169

WIJ:	BWZ20_04180

AHZ:	APS56_05275

TEN:	LPB136_04680

SMIS:

LDL76_01755(neuC)

OAQ:	DZC78_14810(neuC)

FEK:	C1H87_05355(neuC)

MARF:

CJ739_164

PSYN:

E9099_01275(neuC)

LPAL:

LDL79_03605(neuC)

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]