KEGG   ENZYME: 4.2.1.115Help
Entry
EC 4.2.1.115                Enzyme                                 

Name
UDP-N-acetylglucosamine 4,6-dehydratase (configuration-inverting);
FlaA1;
UDP-N-acetylglucosamine 5-inverting 4,6-dehydratase;
PseB;
UDP-N-acetylglucosamine hydro-lyase (inverting;
UDP-2-acetamido-2,6-dideoxy-beta-L-arabino-hex-4-ulose-forming)
Class
Lyases;
Carbon-oxygen lyases;
Hydro-lyases
BRITE hierarchy
Sysname
UDP-N-acetyl-alpha-D-glucosamine hydro-lyase (inverting; UDP-2-acetamido-2,6-dideoxy-beta-L-arabino-hex-4-ulose-forming)
Reaction(IUBMB)
UDP-N-acetyl-alpha-D-glucosamine = UDP-2-acetamido-2,6-dideoxy-beta-L-arabino-hex-4-ulose + H2O [RN:R09697]
Reaction(KEGG)
Substrate
UDP-N-acetyl-alpha-D-glucosamine [CPD:C00043]
Product
UDP-2-acetamido-2,6-dideoxy-beta-L-arabino-hex-4-ulose [CPD:C19823];
H2O [CPD:C00001]
Comment
Contains NADP+ as a cofactor. This is the first enzyme in the biosynthetic pathway of pseudaminic acid [3], a sialic-acid-like sugar that is unique to bacteria and is used by Helicobacter pylori to modify its flagellin. This enzyme plays a critical role in H. pylori's pathogenesis, being involved in the synthesis of both functional flagella and lipopolysaccharides [1,2]. It is completely inhibited by UDP-alpha-D-galactose. The reaction results in the chirality of the C-5 atom being inverted. It is thought that Lys-133 acts sequentially as a catalytic acid, protonating the C-6 hydroxy group and as a catalytic base, abstracting the C-5 proton, resulting in the elimination of water. This enzyme belongs to the short-chain dehydrogenase/reductase family of enzymes.
History
EC 4.2.1.115 created 2009
Pathway
ec00520  Amino sugar and nucleotide sugar metabolism
ec01100  Metabolic pathways
Orthology
K15894  UDP-N-acetylglucosamine 4,6-dehydratase
Genes
ENC: ECL_03364
EBF: D782_1585
PWA: Pecwa_3032
PEC: W5S_3021
PRQ: CYG50_16690(pseB)
PSHI: SAMEA2665130_0849(capD_2)
VCT: JV59_38560
VBR: A6E01_00890
VSC: VSVS12_00342(pseB)
VCC: FAZ90_14255(pseB)
VFM: VFMJ11_0171(pseB)
PPR: PBPRA2711(WS2061)
GHO: AL542_04195(pseB) AL542_05070(pseB)
SALY: E8E00_04300(pseB)
SKS: FCN78_08985(pseB)
SCOT: HBA18_09395(pseB)
PMK: MDS_1966
PPRC: PFLCHA0_c16590(capD1)
PPRO: PPC_1675
PSA: PST_3840
PSEM: TO66_08055
PSIL: PMA3_08485
PKE: DLD99_08345(pseB)
PAR: Psyc_0653(capD)
ABX: ABK1_0086
ADV: DJ533_18140(pseB)
SON: SO_3271(pseB)
SDN: Sden_1286
SBL: Sbal_2967
SLO: Shew_1318
SHL: Shal_1393
SHF: CEQ32_00035(pseB)
SBJ: CF168_14375(pseB)
SHEW: CKQ84_15195(pseB)
CPS: CPS_2092
CBER: B5D82_01865(pseB)
COV: EKO29_16610(pseB)
LSD: EMK97_05500(pseB)
PAT: Patl_3080
PSM: PSM_A2264
PSEO: OM33_07205
PPHE: PP2015_930
PPIS: B1L02_10905(pseB)
PEA: PESP_a2828(pseB)
PSPO: PSPO_a0910(pseB)
PSEN: PNC201_05885(pseB)
PDJ: D0907_14895(pseB)
PAGA: PAGA_a1092(pseB)
MHC: MARHY2546(rkpL)
MAD: HP15_2399
AMAL: I607_05025
AMAE: I876_05320
AMAO: I634_05345
AMAD: I636_05155
AMAI: I635_05125
AMAG: I533_04925
AMAC: MASE_04775
AAUS: EP12_05095
ALR: DS731_06365(pseB)
GNI: GNIT_2393
GPS: C427_3693
CATE: C2869_15785(pseB)
SALM: D0Y50_04610(pseB)
HMI: soil367_06035(pseB)
MVS: MVIS_3754
MYA: MORIYA_3701(pseB)
MMAA: FR932_21305(pseB)
LPM: LP6_0759(capD1)
LPE: lp12_0789
LOK: Loa_00053
LLG: 44548918_01789(capD1)
FPZ: LA55_1649(pseB)
FNA: OOM_1612
FAD: CDH04_02715(pseB)
FMI: F0R74_04835(pseB)
PSAL: PSLF89_935
NHL: Nhal_0393
RHH: E0Z06_10230(pseB)
AEH: Mlg_2322
TVR: TVD_05100
GHL: GM160_03600(pseB)
HAM: HALO0897
PAUR: FGL86_11200(pseB) FGL86_13940(pseB)
KAK: Kalk_15475(pseB)
KGE: TQ33_1405
BMAR: HF888_12090(pseB)
OME: OLMES_3133(wbjB)
AHA: AHA_4150
ASA: ASA_0163
ASR: WL1483_3667(pseB)
ACAV: VI35_07480(pseB)
AEA: C2U39_08120(pseB)
ARV: C7N77_17125(pseB)
AEL: NCTC12917_01571(capD)
THIN: CRN91_03195(pseB)
KKI: KKKWG1_0889(pseB)
ECOR: SAMEA4412678_0519(capD)
EEX: EZJ17_07855(pseB)
CHRI: DK842_04510(pseB)
CRZ: D1345_18325(pseB)
CHRB: DK843_09975(pseB)
PSE: NH8B_3543(capD)
AMAH: DLM_3375
BPH: Bphy_3011
PHS: C2L64_17835(pseB)
PTER: C2L65_15665(pseB)
BPT: Bpet2302
BTRM: SAMEA390648700510(capD)
CTES: O987_16670
JAG: GJA_930
HEE: hmeg3_21310(pseB)
MASZ: C9I28_00225(pseB)
MASY: DPH57_21445(pseB)
MALI: EYF70_30275(pseB)
SDR: SCD_n02907(capD)
DSU: Dsui_0083
ATW: C0099_02460(pseB)
TCL: Tchl_0904
HPY: HP0840
HPJ: jhp_0778
HPG: HPG27_798
HPB: HELPY_0515(flaA1)
HPL: HPB8_1050
HPO: HMPREF4655_20756(pseB)
HPW: hp2018_0823(pseB)
HEF: HPF16_0521(flmA)
HPF: HPF30_0491(flmA)
HEQ: HPF32_0807(flmA)
HEX: HPF57_0862(flmA)
HPZ: HPKB_0505
HPX: HMPREF0462_0567(pseB)
HPYS: HPSA20_0892(pseB)
HPD: KHP_0488(flaA1)
HPYO: HPOK113_0853(flmA)
HPYL: HPOK310_0505(flmA)
HPYR: K747_11220
HPYI: K750_04740
HPYU: K751_04920
HPYM: K749_03075
HEB: U063_1144
HEZ: U064_1148
HHE: HH_1333(flmA)
HAC: Hac_1210(flaA1)
HMS: HMU09920(flaA1)
HFE: HFELIS_04250(flaA1)
HCE: HCW_07265
HCM: HCD_01650
HCP: HCN_1966(flmA)
HCB: HCBAA847_2217(flmA)
HAD: CDV25_00830(pseB)
WSU: WS2061
SUA: Saut_0143
SULR: B649_00715
CJE: Cj1293(pseB)
CJB: BN148_1293(pseB)
CJJ: CJJ81176_1310(flmA)
CJU: C8J_1236
CJI: CJSA_1231(pseB)
CJM: CJM1_1275(flmA)
CJS: CJS3_1390(pseB)
CJEJ: N564_01311
CJEU: N565_01348
CJEN: N755_01343
CJEI: N135_01381
CJER: H730_07415
CJV: MTVDSCj20_1299(pseB)
CJY: QZ67_01428(pseB)
CJQ: UC78_1245(pseB)
CJR: CJE1485(flmA)
CJD: JJD26997_0429(flmA)
CFT: CFF04554_1635(pseB)
CFV: CFVI03293_1657(pseB)
CFX: CFV97608_1760(pseB)
CFZ: CSG_17670
CAMP: CFT03427_1585(pseB)
CCV: CCV52592_0560(pseB)
CLA: CLA_1298(pseB)
CLR: UPTC16701_1281(pseB)
CLM: UPTC16712_1300(pseB)
CLQ: UPTC4110_1284(pseB)
CLN: UPTC3659_1521(pseB)
CLL: CONCH_1251(pseB)
CCQ: N149_1254(pseB)
CCF: YSQ_02395
CCY: YSS_07020
CCOI: YSU_02420
CCOF: VC76_06490(pseB)
CCOO: ATE51_00978(pseB)
CAJ: CIG1485E_1538(pseB)
CIS: CINS_1261(pseB)
CVO: CVOL_1277(pseB)
CPEL: CPEL_1407(pseB)
CAMR: CAQ16704_1310(pseB)
CSM: CSUB8521_1487(pseB)
CSF: CSUB8523_1583(pseB)
CHYO: CHH_1630(pseB)
CHV: CHELV3228_0315(pseB)
CSPF: CSF_1304(pseB)
CPIN: CPIN18020_0090(pseB)
CCUN: CCUN_0611(pseB)
CLX: CLAN_1405(pseB)
CAVI: CAV_1205(pseB)
CHW: A2J15_000555(pseB)
CAMZ: CVIC12175_1417(pseB)
CAMY: CSUIS_1450(pseB)
ABU: Abu_2243(pseB)
ABT: ABED_2053
ABL: A7H1H_2189(pseB)
ASK: EI285_09225(pseB)
AMAR: AMRN_2672(pseB)
ACAA: ACAN_2672(pseB)
APOC: APORC_1986(pseB)
SDL: Sdel_2208
SMUL: SMUL_3172(pseB)
SHAL: SHALO_2907
SULJ: SJPD1_2792
SULT: FA592_06760(pseB)
HYO: NNO_0336
NAM: NAMH_1609
NAP: C3L23_08310(pseB)
CMED: FE773_01450(pseB)
CPAF: C6V80_08975(pseB)
GME: Gmet_0458(pseB)
GEB: GM18_0744
PCA: Pcar_1142(pseB)
DMA: DMR_40270
DCB: C3Y92_20390(pseB)
DPI: BN4_10061
DRT: Dret_0609
DSF: UWK_02414
DAL: Dalk_0626
DBR: Deba_1022
BMX: BMS_0356
BSTO: C0V70_01600(pseB)
MESP: C1M53_01250(pseB)
RPOD: E0E05_09385(pseB)
SMI: BN406_06056(rkpL)
RHI: NGR_b09450(rkpL)
SFH: SFHH103_06319(rkpL)
SIX: BSY16_5641(pseB)
RGR: FZ934_17465(pseB)
ABAW: D5400_05895(pseB)
NWI: Nwi_0643
NHA: Nham_1193
BLAG: BLTE_00520
RBM: TEF_03775
CCR: CC_0233
CAK: Caul_4634
CSE: Cseg_0181
CMB: CSW64_19435(pseB)
CFH: C1707_05025(pseB)
CAUF: CSW63_21395(pseB)
PZU: PHZ_c0080(flmA)
PHB: HYN04_12180(pseB)
MALG: MALG_05070
SPSE: SULPSESMR1_04926(pseB)
HBA: Hbal_0201
GAK: X907_2199
SPHT: K426_25875
ERK: CD351_06885(pseB)
ERF: FIU90_06535(pseB)
ADO: A6F68_00404(pseB)
MAG: amb0716
MGRY: MSR1_01430(pseB)
MAGX: XM1_4680
MAGN: WV31_02410
AZT: TSH58p_18070(pseB)
AZM: DM194_27360(pseB)
AZZ: DEW08_29750(pseB)
NAO: Y958_21720(pseB)
NCB: C0V82_16725(pseB)
MGM: Mmc1_2409
BLI: BL00696
BLD: BLi02205
BAQ: BACAU_1989(capD3)
BAML: BAM5036_1912(ypqP)
BAMA: RBAU_1948(ypqP)
BAMB: BAPNAU_1745(capD1)
BAMT: AJ82_11260
BAO: BAMF_2070(ypqP)
BCE: BC3750
BCX: BCA_3847
BTL: BALH_3382
BTT: HD73_4035
BTHI: BTK_19850
BTM: MC28_2919
BTI: BTG_00625
BWW: bwei_1209(capD)
BMYO: BG05_2274
BMYC: DJ92_3828(pseB)
BPU: BPUM_1899
BPUM: BW16_10405
BPUS: UP12_09700
BMQ: BMQ_pBM60010(flaA1)
BACW: QR42_09655
BACP: SB24_18780
GGH: GHH_c32060(capD)
GEA: GARCT_03180(pseB)
PTB: DER53_12250(pseB)
LYB: C3943_04115(pseB)
LYG: C1N55_04665(pseB)
PSYH: D0S48_07160(pseB)
PPY: PPE_03828
PPM: PPSC2_20125(capD)
PPO: PPM_4033(capD)
PPOL: X809_39510
PPOY: RE92_17065
PLV: ERIC2_c29040(capD)
PSAB: PSAB_18890
PRI: PRIO_5577(pseB)
PSWU: SY83_07090
COH: EAV92_15280(pseB)
JEO: JMA_28210
KUR: ASO14_2417(pseB)
SPOS: DV702_01090(pseB)
CTC: CTC_01712
CBE: Cbei_4282
CBZ: Cbs_4282
CSR: Cspa_c45680(pseB)
CLD: CLSPO_c27850(pseB)
CTAE: BGI42_03920(pseB)
CSEP: CP523_10890(pseB)
AOE: Clos_2515
CAZO: G3A45_09475(pseB)
HSC: HVS_01460(pseB) HVS_04445(capD)
CEW: EKH84_21415(pseB)
SWO: Swol_0227
DAU: Daud_1778
ELM: ELI_2690
HALS: D7D81_05065(pseB)
PFT: JBW_00731
LPIL: LIP_2373
PSNI: NIBR502771_09620(pseB)
BGG: CFK41_06190(pseB)
DAY: FV141_09425(pseB)
LMOI: VV02_10550
CEJ: GC089_14960(pseB)
RAIN: Rai3103_07960(pseB)
SRO: Sros_1199
NOW: GBF35_05345(pseB)
SACC: EYD13_00890(pseB)
AOI: AORI_0252
AJA: AJAP_01310(pseB)
PSEA: WY02_17025
PSEE: FRP1_25720
PSEH: XF36_24825
PAUT: Pdca_01600(rkpL)
MICH: FJK98_09690(pseB)
AMS: AMIS_4210
ACTN: L083_0617
AFS: AFR_02690
PLK: CIK06_15465(pseB)
ABAM: B1s21122_06300(pseB)
ELE: Elen_2421
THEC: FFX45_00730(pseB)
PMT: PMT_0095
PRC: EW14_1498
OXY: HCG48_11640(pseB)
RCA: Rcas_0778
ATM: ANT_06340
ABAT: CFX1CAM_2142(pseB)
PCU: pc0349
PNL: PNK_0397
PUV: PUV_20480(capD)
WCH: wcw_1563(flaA1)
LBF: LBF_1984
ABAC: LuPra_04972(pseB)
FNU: FN1689
TAI: Taci_0679
BVU: BVU_1481
BZG: C4H11_04570(pseB)
BHF: C3V43_13545(pseB)
PARC: CI960_11595(pseB)
PSAC: PSM36_1400(pseB)
PHE: Phep_3947
PGS: CPT03_16795(pseB)
SPDR: G6053_00945(pseB)
EST: DN752_19900(pseB)
CHU: CHU_2766
SLI: Slin_4262
SPIR: CWM47_05795(pseB)
SPIK: EXU85_25840(pseB)
SPIB: G8759_29025(pseB)
RUP: DTQ70_19090(pseB)
FAE: FAES_1126
PSEZ: HME7025_02510(wbpP)
RHOZ: GXP67_20260(pseB)
HSW: Hsw_1660
HNV: DDQ68_04670(pseB)
HYH: D3Y59_06195(pseB)
HYJ: FHG12_00175(pseB)
FLM: MY04_2873(pseB)
CHK: D4L85_11165(pseB)
GFO: GFO_2028
FPAL: HYN49_00355(pseB)
FMG: HYN48_00330(pseB)
DOD: DCS32_13445(pseB)
WIN: WPG_0832
TMAR: MARIT_1562(pseB) MARIT_2532(flnA)
TAJ: C1A40_06860(pseB)
KAN: IMCC3317_43200(pseB)
ANP: FK178_01740(pseB)
FBU: UJ101_00323(wbpP)
FLU: CHH17_13915(pseB)
MRO: MROS_1157
HTH: HTH_1539
GTL: EP073_12665(pseB)
MOX: DAMO_1790
METF: CFE53_01750(pseB)
MSI: Msm_1535
MCUB: MCBB_1289(pseB)
GAH: GAH_01467
MPY: Mpsy_2367
MHU: Mhun_3090
HMU: Hmuk_1471
NMG: Nmag_0147(capD)
NMR: Nmar_0146
NCT: NMSP_0142
NBV: T478_0186
NDV: NDEV_0132(capD)
 » show all
Taxonomy
Reference
1  [PMID:16651261]
  Authors
Ishiyama N, Creuzenet C, Miller WL, Demendi M, Anderson EM, Harauz G, Lam JS, Berghuis AM
  Title
Structural studies of FlaA1 from Helicobacter pylori reveal the mechanism for inverting 4,6-dehydratase activity.
  Journal
J Biol Chem 281:24489-95 (2006)
DOI:10.1074/jbc.M602393200
  Sequence
[hpy:HP0840]
Reference
2  [PMID:12791140]
  Authors
Schirm M, Soo EC, Aubry AJ, Austin J, Thibault P, Logan SM
  Title
Structural, genetic and functional characterization of the flagellin glycosylation process in Helicobacter pylori.
  Journal
Mol Microbiol 48:1579-92 (2003)
DOI:10.1046/j.1365-2958.2003.03527.x
  Sequence
[hpy:HP0840]
Reference
3  [PMID:16751642]
  Authors
Schoenhofen IC, McNally DJ, Brisson JR, Logan SM
  Title
Elucidation of the CMP-pseudaminic acid pathway in Helicobacter pylori: synthesis from UDP-N-acetylglucosamine by a single enzymatic reaction.
  Journal
Glycobiology 16:8C-14C (2006)
DOI:10.1093/glycob/cwl010
  Sequence
[hpy:HP0840]
Other DBs
ExplorEnz - The Enzyme Database: 4.2.1.115
IUBMB Enzyme Nomenclature: 4.2.1.115
ExPASy - ENZYME nomenclature database: 4.2.1.115
BRENDA, the Enzyme Database: 4.2.1.115

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