4.2.1.46: dTDP-glucose 4,6-dehydratase
This is an abbreviated version!
For detailed information about dTDP-glucose 4,6-dehydratase, go to the full flat file.
Word Map on EC 4.2.1.46
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4.2.1.46
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dtdp-l-rhamnose
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dtdp-4-keto-6-deoxy-d-glucose
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3,5-epimerase
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dtdp-4-dehydrorhamnose
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o-antigen
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deoxysugars
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dtmp
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thymidylyltransferase
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6-deoxyhexose
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peucetius
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analysis
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synthesis
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pharmacology
- 4.2.1.46
- dtdp-l-rhamnose
- dtdp-4-keto-6-deoxy-d-glucose
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3,5-epimerase
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dtdp-4-dehydrorhamnose
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o-antigen
-
deoxysugars
- dtmp
-
thymidylyltransferase
-
6-deoxyhexose
- peucetius
- analysis
- synthesis
- pharmacology
Reaction
Synonyms
DesIV, dTDP-D-glucose 4,6-dehydratase, dTDP-D-glucose oxidoreductase, dTDP-glucose-4,6-dehydratase, dTGD, RmbB, rml-2, RmlB, TDP-D-glucose 4,6-dehydratase, TDP-glucose oxidoreductase, TDPDH, Thymidine diphosphate D-glucose oxidoreductase, thymidine diphosphate-glucose 4,6-dehydratase, Thymidine diphospho-D-glucose 4,6-dehydratase, Thymidine diphosphoglucose oxidoreductase, UDP-D-glucose 4,6-dehydratase, Ugd
ECTree
4.2.1.46 dTDP-glucose 4,6-dehydrataseAdvanced search results
results (
results (Substrates Products
Substrates Products on EC 4.2.1.46 - dTDP-glucose 4,6-dehydratase
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SUBSTRATE 
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
dTDP-3-azido-3-deoxy-D-glucose
dTDP-3-azido-3,6-dideoxy-alpha-D-xylo-hexopyran-4-ulose
-
-
-
?
dTDP-3-deoxy-D-glucose
dTDP-3,6-dideoxy-alpha-D-erythro-hexopyran-4-ulose
-
-
-
?
dTDP-6-fluoro-6-deoxyglucose
dTDP-4-keto-6-deoxyglucose + F-
substrate undergoes fluoride ion elimination instead of dehydration
-
?
dTDP-alpha-D-glucose
dTDP-4-dehydro-6-deoxy-alpha-D-glucose + H2O
-
-
-
-
?
dTDP-alpha-D-glucose
dTDP-4-dehydro-6-deoxy-alpha-D-glucose + H2O
-
-
-
-
?
dTDP-alpha-D-glucose
dTDP-4-dehydro-6-deoxy-alpha-D-glucose + H2O
-
-
-
?
dTDP-alpha-D-glucose
dTDP-4-dehydro-6-deoxy-alpha-D-glucose + H2O
the enzyme is specifically active toward dTDP-Glc, showing little, if any, activity toward UDP-Glc and no activity toward other potential NDP-glucose substrates or toward several NDP-sugars that are abundant in Caenorhabditis elegans (e.g. GDP-Man, UDP-GlcNAc and UDPGal)
-
-
?
dTDP-alpha-D-glucose
dTDP-4-dehydro-6-deoxy-alpha-D-glucose + H2O
-
-
-
?
dTDP-alpha-D-glucose
dTDP-4-dehydro-6-deoxy-alpha-D-glucose + H2O
the enzyme is involved in the biosynthesis of the dTDP-3-amino-3,6-dideoxy-D-galactose and dTDP-3-amino-3,6-dideoxy-D-glucose
-
-
?
dTDP-alpha-D-glucose
dTDP-4-dehydro-6-deoxy-alpha-D-glucose + H2O
-
-
-
-
?
dTDP-alpha-D-glucose
dTDP-4-dehydro-6-deoxy-alpha-D-glucose + H2O
-
-
-
-
?
dTDP-alpha-D-glucose
dTDP-4-dehydro-6-deoxy-alpha-D-glucose + H2O
-
-
-
-
?
dTDP-alpha-D-glucose
dTDP-4-dehydro-6-deoxy-alpha-D-glucose + H2O
-
-
-
-
?
dTDP-alpha-D-glucose
dTDP-4-dehydro-6-deoxy-alpha-D-glucose + H2O
-
-
-
-
?
dTDP-alpha-D-glucose
dTDP-4-dehydro-6-deoxy-alpha-D-glucose + H2O
-
-
-
-
?
dTDP-alpha-D-glucose
dTDP-4-dehydro-6-deoxy-alpha-D-glucose + H2O
-
-
-
-
?
dTDP-alpha-D-glucose
dTDP-4-dehydro-6-deoxy-alpha-D-glucose + H2O
-
-
-
-
?
dTDP-alpha-D-glucose
dTDP-4-dehydro-6-deoxy-alpha-D-glucose + H2O
-
-
-
-
?
dTDP-alpha-D-glucose
dTDP-4-dehydro-6-deoxy-alpha-D-glucose + H2O
-
-
-
-
?
dTDP-alpha-D-glucose
dTDP-4-dehydro-6-deoxy-alpha-D-glucose + H2O
-
-
-
-
?
dTDP-alpha-D-glucose
dTDP-4-dehydro-6-deoxy-alpha-D-glucose + H2O
-
-
-
-
?
dTDP-alpha-D-glucose
dTDP-4-dehydro-6-deoxy-alpha-D-glucose + H2O
-
-
-
-
?
dTDP-alpha-D-glucose
dTDP-4-dehydro-6-deoxy-alpha-D-glucose + H2O
-
-
-
-
?
dTDP-alpha-D-glucose
dTDP-4-dehydro-6-deoxy-alpha-D-glucose + H2O
-
-
-
?
dTDP-alpha-D-glucose
dTDP-4-dehydro-6-deoxy-alpha-D-glucose + H2O
-
-
-
?
dTDP-alpha-D-glucose
dTDP-4-dehydro-6-deoxy-alpha-D-glucose + H2O
-
-
-
-
?
dTDP-alpha-D-glucose
dTDP-4-dehydro-6-deoxy-alpha-D-glucose + H2O
-
-
-
-
?
dTDP-alpha-D-glucose
dTDP-4-dehydro-6-deoxy-alpha-D-glucose + H2O
-
-
-
-
?
dTDP-alpha-D-glucose
dTDP-4-dehydro-6-deoxy-alpha-D-glucose + H2O
-
-
-
-
?
dTDP-alpha-D-glucose
dTDP-4-dehydro-6-deoxy-alpha-D-glucose + H2O
-
-
-
-
?
dTDP-alpha-D-glucose
dTDP-4-dehydro-6-deoxy-alpha-D-glucose + H2O
-
-
-
-
?
dTDP-alpha-D-glucose
dTDP-4-dehydro-6-deoxy-alpha-D-glucose + H2O
-
-
-
-
?
dTDP-alpha-D-glucose
dTDP-4-dehydro-6-deoxy-alpha-D-glucose + H2O
-
-
-
-
?
dTDP-alpha-D-glucose
dTDP-4-dehydro-6-deoxy-alpha-D-glucose + H2O
-
-
-
-
?
dTDP-alpha-D-glucose
dTDP-4-dehydro-6-deoxy-alpha-D-glucose + H2O
-
-
-
-
?
dTDP-alpha-D-glucose
dTDP-4-dehydro-6-deoxy-alpha-D-glucose + H2O
-
-
-
-
?
dTDP-alpha-D-glucose
dTDP-4-dehydro-6-deoxy-alpha-D-glucose + H2O
-
-
-
-
?
dTDP-alpha-D-glucose
dTDP-4-dehydro-6-deoxy-alpha-D-glucose + H2O
-
-
-
-
?
dTDP-alpha-D-glucose
dTDP-4-dehydro-6-deoxy-alpha-D-glucose + H2O
-
-
-
-
?
dTDP-alpha-D-glucose
dTDP-4-dehydro-6-deoxy-alpha-D-glucose + H2O
-
-
-
-
?
dTDP-alpha-D-glucose
dTDP-4-dehydro-6-deoxy-alpha-D-glucose + H2O
-
-
-
-
?
dTDP-alpha-D-glucose
dTDP-4-dehydro-6-deoxy-alpha-D-glucose + H2O
-
-
-
-
?
dTDP-alpha-D-glucose
dTDP-4-dehydro-6-deoxy-alpha-D-glucose + H2O
-
-
-
?
dTDP-alpha-D-glucose
dTDP-4-dehydro-6-deoxy-alpha-D-glucose + H2O
QM/MM investigation of the detailed mechanism of dTDP-glucose 4,6-dehydratase. The computational results demonstrate that the whole catalytic reaction contains four enzymatic elementary steps and one nonenzymatic enol-keto tautomerisation step. In the oxidation step, the NAD+ abstracts the hydride from glycosyl C4 and a conserved tyrosine residue removes a proton from the glycosyl C4-hydroxyl group. This oxidation step proceeds through a concerted asynchronous mechanism with a calculated free energy barrier of 21.1 kcal/mol, in which the hydride transfer lags behind the proton transfer. Different from the proposal based on experiments that the dehydration follows a concerted mechanism. The QM/MM calculation results show that the elimination of water is stepwise, in which two highly conserved residues are involved. Glu129 firstly deprotonates the glycosyl C5 and subsequently Asp128 protonates the leaving C6-hydroxyl group to give a water molecule and dTDP-4-dehydroglucose-5,6-ene intermediate. In the reduction step, NADH returns the hydride back to glycosyl C6 and the phenolic hydroxyl of Tyr151 spontaneously denotes its proton to C4-keto group, forming an enol
-
-
?
dTDP-alpha-D-glucose
dTDP-4-dehydro-6-deoxy-alpha-D-glucose + H2O
-
-
-
-
?
dTDP-alpha-D-glucose
dTDP-4-dehydro-6-deoxy-alpha-D-glucose + H2O
-
-
-
-
?
dTDP-alpha-D-glucose
dTDP-4-dehydro-6-deoxy-alpha-D-glucose + H2O
-
-
-
-
?
dTDP-glucose
?
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key role in biosynthesis of macrolides and other types of antibiotics
-
-
?
dTDP-glucose
dTDP-4-dehydro-6-deoxy-D-glucose + H2O
-
the conversion takes place in three steps: dehydrogenation to dTDP-4-ketoglucose, dehydration to dTDP-4-ketoglucose-5,6-ene and rereduction of C6 to the methyl group
-
?
dTDP-glucose
dTDP-4-dehydro-6-deoxy-D-glucose + H2O
the conversion takes place in three steps: dehydrogenation to dTDP-4-ketoglucose, dehydration to dTDP-4-ketoglucose-5,6-ene and rereduction of C6 to the methyl group. Asp135 and Glu136 are the acid and base catalysts, respectively of the dehydration step
-
?
dTDP-glucose
dTDP-4-dehydro-6-deoxy-D-glucose + H2O
the single-turnover kinetic mechanism for the reaction is determined by rapid mix-chemical quench mass spectrometry. NAD+ initially oxidizes glucosyl C4 of dTDP-glucose to NADH and dTDP-4-ketoglucose. Next water is eliminated between C5 and C6 of dTDP-4-ketoglucose to form dTDP-4-ketoglucose-5,6-ene. Hydride transfer from NADH to C6 of dTDP-4-ketoglucose-5,6-ene regenerates NAD+ and produces the product dTDP-4-keto-4-deoxyglucose
-
?
dTDP-glucose
dTDP-4-dehydro-6-deoxy-D-glucose + H2O
-
second enzyme in the dTDP-L-rhamnose pathway
-
?
dTDP-glucose
dTDP-4-dehydro-6-deoxy-D-glucose + H2O
-
second enzyme of the dTDP-L-rhamnose synthesis pathway
-
?
dTDP-glucose
dTDP-4-dehydro-6-deoxy-D-glucose + H2O
-
-
-
?
dTDP-glucose
dTDP-4-dehydro-6-deoxy-D-glucose + H2O
-
-
-
?
dTDP-glucose
dTDP-4-dehydro-6-deoxy-D-glucose + H2O
-
-
-
?
dTDP-glucose
dTDP-4-dehydro-6-deoxy-D-glucose + H2O
-
-
-
?
dTDP-glucose
dTDP-4-dehydro-6-deoxy-D-glucose + H2O
enzyme consists of a C-terminal sugar-nucleotide binding domain and an N-terminal NAD+ cofactor-binding domain
-
-
?
dTDP-glucose
dTDP-4-dehydro-6-deoxy-D-glucose + H2O
involved in initial steps of glycan biosynthesis of bacterial cell surface layer (S-layer)
-
-
?
dTDP-glucose
dTDP-4-dehydro-6-deoxy-D-glucose + H2O
involved in initial steps of glycan biosynthesis of bacterial cell surface layer (S-layer)
-
-
?
UDP-D-glucose
UDP-4-dehydro-6-deoxy-D-glucose + H2O
E3VXL5
-
-
-
?
UDP-D-glucose
UDP-4-dehydro-6-deoxy-D-glucose + H2O
-
-
-
?
additional information
?
-
-
not: ADPglucose, CDPglucose, UDPglucose, GDPglucose, UDPgalactose, dTDPmannose, CTP and dTTP
-
-
?
additional information
?
-
-
enzyme of the 6-deoxyhexose biosynthetic pathway, that is also present in the aminoglycoside antibiotic biosynthetic pathway
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-
?
additional information
?
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-
not: ADPglucose, ADPmannose, GDPmannose, GDPglucose, UDPgalactose
-
-
?
additional information
?
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-
not: ADPglucose, ADPmannose, GDPmannose, GDPglucose, UDPgalactose
-
-
?
