KEGG   ORTHOLOGY: K16435Help
Entry
K16435                      KO                                     

Name
evaA, eryBVI, tylCVI, tylX3, staJ
Definition
dTDP-4-dehydro-6-deoxy-alpha-D-glucopyranose 2,3-dehydratase [EC:4.2.1.159]
Pathway
ko00523  Polyketide sugar unit biosynthesis
ko01055  Biosynthesis of vancomycin group antibiotics
ko01100  Metabolic pathways
ko01130  Biosynthesis of antibiotics
Module
M00798  dTDP-L-mycarose biosynthesis
M00799  dTDP-L-oleandrose biosynthesis
M00800  dTDP-L-megosamine biosynthesis
M00801  dTDP-L-olivose biosynthesis
M00802  dTDP-D-forosamine biosynthesis
M00803  dTDP-D-angolosamine biosynthesis
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09109 Metabolism of terpenoids and polyketides
   00523 Polyketide sugar unit biosynthesis
    K16435  evaA, eryBVI, tylCVI, tylX3, staJ; dTDP-4-dehydro-6-deoxy-alpha-D-glucopyranose 2,3-dehydratase
   01055 Biosynthesis of vancomycin group antibiotics
    K16435  evaA, eryBVI, tylCVI, tylX3, staJ; dTDP-4-dehydro-6-deoxy-alpha-D-glucopyranose 2,3-dehydratase
Enzymes [BR:ko01000]
 4. Lyases
  4.2  Carbon-oxygen lyases
   4.2.1  Hydro-lyases
    4.2.1.159  dTDP-4-dehydro-6-deoxy-alpha-D-glucopyranose 2,3-dehydratase
     K16435  evaA, eryBVI, tylCVI, tylX3, staJ; dTDP-4-dehydro-6-deoxy-alpha-D-glucopyranose 2,3-dehydratase
BRITE hierarchy
Other DBs
RN: R05518 R06428
Genes
VCX: VAA049_3444
SDE: Sde_2127
GUR: Gura_4278
GBM: Gbem_3308
GEO: Geob_0428
GEM: GM21_0940
DMA: DMR_07580
DSA: Desal_3612
HOE: IMCC20628_04711
BGZ: XH91_11595
SHUM: STHU_14710
TPR: Tpau_3481
SALB: XNR_0600
SMA: SAVERM_950(aveBVI)
SGR: SGR_633
SVE: SVEN_5994
SFI: SFUL_5272
SALU: DC74_6604
SALL: SAZ_34335
STRE: GZL_01620
SLD: T261_6842
SAMB: SAM23877_5618(srm19)
SLE: sle_09630(sle_09630)
SNR: SNOUR_06865 SNOUR_10090(eryBVI)
SMAL: SMALA_7128
SALJ: SMD11_1662
SFK: KY5_2324
NDA: Ndas_4708
NAL: B005_1432
TCU: Tcur_2760
SEN: SACE_0717(eryBVI)
AMD: AMED_0645
AOI: AORI_1498
PSEH: XF36_05045
PHH: AFB00_29740(selSVII)
SESP: BN6_58920(sam31)
KAL: KALB_6582(acuS4)
ACAD: UA74_05670
ALO: CRK56087
MIL: ML5_4434
BFR: BF0809
GFO: GFO_2035
NBV: T478_0170
AG: AAD55451(oleV) AAF29379(tylCVI) AAG23276(spnO) AAK01936(jadO) ABV49606(ang-ORF4) BAC55214(staJ) CAK50786(mtmV)
 » show all
TaxonomyKoalaUniProt
Reference
  Authors
Xu L, Huang H, Wei W, Zhong Y, Tang B, Yuan H, Zhu L, Huang W, Ge M, Yang S, Zheng H, Jiang W, Chen D, Zhao GP, Zhao W
  Title
Complete genome sequence and comparative genomic analyses of the vancomycin-producing Amycolatopsis orientalis.
  Journal
BMC Genomics 15:363 (2014)
DOI:10.1186/1471-2164-15-363
  Sequence
[aoi:AORI_1498]
Reference
  Authors
Bate N, Butler AR, Smith IP, Cundliffe E
  Title
The mycarose-biosynthetic genes of Streptomyces fradiae, producer of tylosin.
  Journal
Microbiology 146 ( Pt 1):139-46 (2000)
DOI:10.1099/00221287-146-1-139
  Sequence
Reference
  Authors
Onaka H, Taniguchi S, Igarashi Y, Furumai T
  Title
Cloning of the staurosporine biosynthetic gene cluster from Streptomyces sp. TP-A0274 and its heterologous expression in Streptomyces lividans.
  Journal
J Antibiot (Tokyo) 55:1063-71 (2002)
DOI:10.7164/antibiotics.55.1063
  Sequence

KEGG   ENZYME: 4.2.1.159Help
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
BRITE hierarchy
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)
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
ec01130  Biosynthesis of antibiotics
Orthology
K16435  dTDP-4-dehydro-6-deoxy-alpha-D-glucopyranose 2,3-dehydratase
Genes
VCX: VAA049_3444
SDE: Sde_2127
GUR: Gura_4278
GBM: Gbem_3308
GEO: Geob_0428
GEM: GM21_0940
DMA: DMR_07580
DSA: Desal_3612
HOE: IMCC20628_04711
BGZ: XH91_11595
SHUM: STHU_14710
TPR: Tpau_3481
SALB: XNR_0600
SMA: SAVERM_950(aveBVI)
SGR: SGR_633
SVE: SVEN_5994
SFI: SFUL_5272
SALU: DC74_6604
SALL: SAZ_34335
STRE: GZL_01620
SLD: T261_6842
SAMB: SAM23877_5618(srm19)
SLE: sle_09630(sle_09630)
SNR: SNOUR_06865 SNOUR_10090(eryBVI)
SMAL: SMALA_7128
SALJ: SMD11_1662
SFK: KY5_2324
NDA: Ndas_4708
NAL: B005_1432
TCU: Tcur_2760
SEN: SACE_0717(eryBVI)
AMD: AMED_0645
AOI: AORI_1498
PSEH: XF36_05045
PHH: AFB00_29740(selSVII)
SESP: BN6_58920(sam31)
KAL: KALB_6582(acuS4)
ACAD: UA74_05670
ALO: CRK56087
MIL: ML5_4434
BFR: BF0809
GFO: GFO_2035
NBV: T478_0170
 » show all
Taxonomy
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
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
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
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
Reference
6  [PMID:20418422]
  Authors
Useglio M, Peiru S, Rodriguez E, Labadie GR, Carney JR, Gramajo H
  Title
TDP-L-megosamine biosynthesis pathway elucidation and megalomicin a production in Escherichia coli.
  Journal
Appl Environ Microbiol 76:3869-77 (2010)
DOI:10.1128/AEM.03083-09
Other DBs
ExplorEnz - The Enzyme Database: 4.2.1.159
IUBMB Enzyme Nomenclature: 4.2.1.159
ExPASy - ENZYME nomenclature database: 4.2.1.159
BRENDA, the Enzyme Database: 4.2.1.159

KEGG   REACTION: R05518Help
Entry
R05518                      Reaction                               

Name
dTDP-4-dehydro-6-deoxy-alpha-D-glucopyranose hydro-lyase (dTDP-2,6-dideoxy-D-glycero-hex-2-enos-4-ulose-forming)
Definition
dTDP-4-oxo-6-deoxy-D-glucose <=> dTDP-3,4-dioxo-2,6-dideoxy-D-glucose + H2O
Equation
Reaction class
RC00782  C06620_C11907
Enzyme
Pathway
rn00523  Polyketide sugar unit biosynthesis
rn01055  Biosynthesis of vancomycin group antibiotics
rn01100  Metabolic pathways
rn01130  Biosynthesis of antibiotics
Module
M00798  dTDP-L-mycarose biosynthesis
M00799  dTDP-L-oleandrose biosynthesis
M00800  dTDP-L-megosamine biosynthesis
M00801  dTDP-L-olivose biosynthesis
M00802  dTDP-D-forosamine biosynthesis
M00803  dTDP-D-angolosamine biosynthesis
Orthology
K16435  dTDP-4-dehydro-6-deoxy-alpha-D-glucopyranose 2,3-dehydratase [EC:4.2.1.159]
Other DBs
RHEA: 47975

DBGET integrated database retrieval system