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
Orthology
K15894  UDP-N-acetylglucosamine 4,6-dehydratase
Genes
GHO: AL542_04195(pseB)
PPW: PputW619_3711
PPRC: PFLCHA0_c16590(capD1)
PPRO: PPC_1675
PFO: Pfl01_1518
PFE: PSF113_1546
PSV: PVLB_17290
PCH: EY04_07650
PCZ: PCL1606_44800
PCP: JM49_22220
PSEM: TO66_08055
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)
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)
AMAL: I607_05025
AMAE: I876_05320
AMAO: I634_05345
AMAD: I636_05155
AMAI: I635_05125
AMAG: I533_04925
AMAC: MASE_04775
AAUS: EP12_05095
GNI: GNIT_2393
GPS: C427_3693
CATE: C2869_15785(pseB)
MVS: MVIS_3754
MYA: MORIYA_3701(pseB)
LPM: LP6_0759(capD1)
LPE: lp12_0789
LLG: 44548918_01789(capD1)
FPZ: LA55_1649(pseB)
FNA: OOM_1612
PSAL: PSLF89_935
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)
CHRI: DK842_04510(pseB)
BPH: Bphy_3011
PHS: C2L64_17835(pseB)
PTER: C2L65_15665(pseB)
HEE: hmeg3_21310(pseB)
MASZ: C9I28_00225(pseB)
MASY: DPH57_21445(pseB)
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
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)
ABU: Abu_2243(pseB)
ABT: ABED_2053
ABL: A7H1H_2189(pseB)
SDL: Sdel_2208
SMUL: SMUL_3172(pseB)
SHAL: SHALO_2907
SULJ: SJPD1_2792
NAM: NAMH_1609
DRT: Dret_0609
DSF: UWK_02414
NWI: Nwi_0643
NHA: Nham_1193
CCR: CC_0233
CAK: Caul_4634
CSE: Cseg_0181
CMB: CSW64_19435(pseB)
PZU: PHZ_c0080(flmA)
PHB: HYN04_12180(pseB)
MALG: MALG_05070
HBA: Hbal_0201
MAG: amb0716
MAGX: XM1_4680
MAGN: WV31_02410
AZT: TSH58p_18070(pseB)
AZM: DM194_27360(pseB)
NAO: Y958_21720(pseB)
NCB: C0V82_16725(pseB)
MGM: Mmc1_2409
BMYC: DJ92_3828(pseB)
LYB: C3943_04115(pseB)
JEO: JMA_28210
PFT: JBW_00731
PSEE: FRP1_25720
PSEH: XF36_24825
AMS: AMIS_4210
ACTN: L083_0617
AFS: AFR_02690
PLK: CIK06_15465(pseB)
ABAM: B1s21122_06300(pseB)
PCU: pc0349
PNL: PNK_0397
PUV: PUV_20480(capD)
WCH: wcw_1563(flaA1)
TAI: Taci_0679
NMR: Nmar_0146
NIN: NADRNF5_2119(pseB)
NCT: NMSP_0142
 » 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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