KEGG   ENZYME: 4.2.1.159
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
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
ec01110  Biosynthesis of secondary metabolites
Orthology
K16435  dTDP-4-dehydro-6-deoxy-alpha-D-glucopyranose 2,3-dehydratase
Genes
VCXVAA049_3444
SDESde_2127
REVHUE57_13920
AMONH9L24_02340
HTNKI616_09480
GEMGM21_0940
GURGura_4278
GEOGeob_0428
GBMGbem_3308
GBNGEOBRER4_09090
DMADMR_07580
DCBC3Y92_16665
DSADesal_3612
HOEIMCC20628_04711
BGZXH91_11595
MMRMmar10_0545
SHUMSTHU_14710
LYGC1N55_04675
LLFBCR17_06565
WDIH9L19_07475
LBWC3V36_01190
DORDesor_5131
DMIDesmer_4107
CIUG4D55_18805
LCGL3BBH23_23160
NBRO3I_007495 O3I_015250
NTPCRH09_07965 CRH09_20630
NWLNWFMUON74_25900
NIEKV110_14290 KV110_35800
TPRTpau_3481
DPCA6048_11420
SALBXNR_0600
SMASAVERM_950(aveBVI)
SGRSGR_633
SCBSCAB_83991
SVLStrvi_3809
SRCM271_00405 M271_06420
SMALSMALA_7128
SSOII1A49_39420
SBHSBI_01545 SBI_06874
SVESVEN_5994
SDVBN159_2519
SALSSLNWT_0705 SLNWT_7313
SFISFUL_5272
SCIB446_13490
SALUDC74_6604
SALLSAZ_34335
SVTSVTN_18805
STREGZL_01620
SLDT261_6842
SLCSL103_12590
SXISXIM_35760
SAMBSAM23877_5618(srm19)
SPRISPRI_0250 SPRI_7103
SCXAS200_01290
SRWTUE45_01318
SLEsle_09630(sle_09630)
SRNA4G23_02281
SPAVSpa2297_32825
SCLFBB341_29660
SGSAVL59_46210
SALWCP975_00340
SGMGCM10017557_01740 GCM10017557_73700
SCADDN051_13660
SPHWNFX46_24940
SNRSNOUR_06865 SNOUR_10090(eryBVI)
SNWBBN63_25020
SAUOBV401_39270
SVUB1H20_22670 B1H20_29860
SPUNBFF78_11180
SALFSMD44_08278
SALJSMD11_1662
SLXSLAV_40175
STROSTRMOE7_07500
SFKKY5_2324
SLKSLUN_13805
SDXC4B68_09680
SGDELQ87_00890 ELQ87_08060
SNQCP978_29670
STIRDDW44_27815
SKACP970_30865 CP970_39800
SRKFGW37_16325
SFICEIZ62_04075 EIZ62_09585
SGALCP966_29035
SSPODDQ41_30680
SPADDVK44_01735
SGFHEP81_07930
SCAVCVT27_24440
SRIMCP984_10770
SPHVF9278_28220
SCINCP977_28090
SPACB1H29_00715 B1H29_36345
STSUB7R87_22130
SCHACP983_27975
SCOECP976_32945
SBROGQF42_07475
SCHFIPT68_29240
SHUNDWB77_05139
SHARHUT13_24970
SCYGS1361_05000 S1361_29920
SFEUIM697_37735
SLIAHA039_05635
SDWK7C20_32610
SCALI6J39_29665
SAUHSU9_032835
SFBCP974_12555
SMOBJ7W19_17605 J7W19_28800
SPEUCGZ69_24345
SXNIAG42_36010
SGJIAG43_33090
SHKJ2N69_28810
SANUK7396_04485 K7396_33455
SDDD9753_11220
SMAOCAG99_12095
SGOBtest1122_15665
SINEKI385_25275
SLFJEQ17_40470
SDECL3078_20655
KABB7C62_31105
STRIC7M71_025695 C7M71_025875
YIALO772_07335
ABRYNYE86_15410 NYE86_16010
ARUBJ5A65_00460
AERAERYTH_15845
TALXFOF52_07490 FOF52_14775
NDANdas_4708
NALB005_1432
NGVCDO52_02795
NFEHUT17_04685
STRREKD16_15560
TCUTcur_2760
ACTWF7P10_30175 F7P10_30200
AGRAAGRA3207_007759
NOWGBF35_40110
NCXNocox_25610
FRAFrancci3_4134
SENSACE_0717(eryBVI)
SACGFDZ84_24205
SVISvir_29870
SACCEYD13_16500
AMDAMED_0645 AMED_5402
AMNRAM_03295 RAM_27540
AMMAMES_0643 AMES_5337
AMZB737_0644 B737_5337
AOIAORI_1498
AJAAJAP_32030
AMYCCU254_17440
AMYBBKN51_41530
AABA4R43_01810
AMYYYIM_08355 YIM_11645 YIM_22855
AORISD37_33630 SD37_34285
APRTMUY14_22470
AROONQK81_15400
PSEHXF36_05045
PSEQAD006_29960
PECQAD017_31290
PHHAFB00_29740(selSVII)
SESPBN6_58920(sam31)
SSYIEKG83_32265
KALKALB_6582(acuS4)
KPHYAOZ06_22485 AOZ06_23375
LEDBBK82_43750
AHMTL08_05635 TL08_15940
ACTIUA75_05675 UA75_16845
ACADUA74_05670
AHGAHOG_05435 AHOG_15160 AHOG_15195
ACTAC1701_01560 C1701_26015
ALOCRK56087
PMADBAY61_07755
ACTUActkin_00393 Actkin_02428(perS10)
STPStrop_2181
SAQSare_1267 Sare_2340
MAUMicau_3987
MILML5_4434
MICBMicB006_4920
MCABHXZ27_04100(evdS9)
MCRAID554_11975 ID554_28100
AMSAMIS_50580
PLKCIK06_11040
PSUUPsuf_058320 Psuf_058570
VERHUT12_18885
DVCDvina_05940 Dvina_31405
DFUDfulv_18280 Dfulv_29145
DROSDrose_26850
DAURDaura_30065 Daura_37965
NHYJQS43_06855
CCAZCOUCH_16050
AEYCDG81_13205
CYICBM981_2305
LKBLPTSP3_g21200
EDAGWR55_15460
BFRBF0809
BFBVU15_03400
BCELBcellWH2_00546 BcellWH2_04965
ASXCDL62_18260
RUFTH63_02825
GFOGFO_2035
FNKE1750_13615
FBUUJ101_00308 UJ101_00547
PROCPtc2401_00807
NBVT478_0170
 » show all
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

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