4.3.1.30: dTDP-4-amino-4,6-dideoxy-D-glucose ammonia-lyase
This is an abbreviated version!
For detailed information about dTDP-4-amino-4,6-dideoxy-D-glucose ammonia-lyase, go to the full flat file.
Word Map on EC 4.3.1.30
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4.3.1.30
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deamination
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dehydrogenation
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s-adenosyl-l-methionine
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venezuelae
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desosamine
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radical-mediated
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deuterium
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ketone
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deprotonation
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dehydrogenases
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5\'-deoxyadenosyl
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epr
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homolysis
- 4.3.1.30
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deamination
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dehydrogenation
- s-adenosyl-l-methionine
- venezuelae
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desosamine
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radical-mediated
- deuterium
- ketone
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deprotonation
- dehydrogenases
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5\'-deoxyadenosyl
- epr
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homolysis
Reaction
Synonyms
DesII
ECTree
4.3.1.30 dTDP-4-amino-4,6-dideoxy-D-glucose ammonia-lyaseAdvanced search results
results (
results (Substrates Products
Substrates Products on EC 4.3.1.30 - dTDP-4-amino-4,6-dideoxy-D-glucose ammonia-lyase
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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-4-amino-4,6-dideoxy-alpha-D-glucopyranose + S-adenosyl-L-methionine
dTDP-3-dehydro-4,6-dideoxy-alpha-D-glucopyranose + NH3 + L-methionine + 5'-deoxyadenosine
dTDP-4-amino-4,6-dideoxy-alpha-D-glucopyranose + S-adenosyl-L-methionine + reduced acceptor
dTDP-3-dehydro-4,6-dideoxy-alpha-D-glucopyranose + NH3 + L-methionine + 5'-deoxyadenosine + acceptor
dTDP-4-amino-4,6-dideoxy-D-glucopyranose + S-adenosyl-L-methionine
dTDP-3-dehydro-4,6-dideoxy-alpha-D-glucopyranose + NH3 + L-methionine + 5'-deoxyadenosine
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-
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?
TDP-4-amino-4-deoxy-D-fucose + S-adenosyl-L-methionine + reduced acceptor
?
TDP-4-amino-4-deoxy-D-fucose undergoes deamination alone with a specific activity that is 3fold reduced with respect to deamination of dTDP-4-amino-4,6-dideoxy-alpha-D-glucopyranose. A mechanism is proposed involving direct elimination of ammonium concerted with proton transfer to the nucleofuge from the adjacent alpha-hydroxyalkyl radical
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-
?
dTDP-4-amino-4,6-dideoxy-alpha-D-glucopyranose + S-adenosyl-L-methionine
dTDP-3-dehydro-4,6-dideoxy-alpha-D-glucopyranose + NH3 + L-methionine + 5'-deoxyadenosine
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-
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?
dTDP-4-amino-4,6-dideoxy-alpha-D-glucopyranose + S-adenosyl-L-methionine
dTDP-3-dehydro-4,6-dideoxy-alpha-D-glucopyranose + NH3 + L-methionine + 5'-deoxyadenosine
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the enzyme is involved in biosynthesis of TDP-D-desosamine
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-
?
dTDP-4-amino-4,6-dideoxy-alpha-D-glucopyranose + S-adenosyl-L-methionine
dTDP-3-dehydro-4,6-dideoxy-alpha-D-glucopyranose + NH3 + L-methionine + 5'-deoxyadenosine
the enzyme is involved in biosynthesis of TDP-D-desosamine
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-
?
dTDP-4-amino-4,6-dideoxy-alpha-D-glucopyranose + S-adenosyl-L-methionine
dTDP-3-dehydro-4,6-dideoxy-alpha-D-glucopyranose + NH3 + L-methionine + 5'-deoxyadenosine
studies of deuterium incorporation into S-adenosyl-L-methionine using TDP-[3-2H]-4-amino-4,6-dideoxy-D-glucose as the substrate provides strong evidence for direct hydrogen atom transfer to a 5'-deoxyadenosyl radical in the catalytic cycle. The fact that hydrogen atom abstraction occurs at C3 also sheds light on the mechanism of this intriguing deamination reaction. Generation of a 5'-deoxyadenosyl radical is expected to be the first part of the reaction facilitated by the reduced [4Fe-4S]1+ cluster
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-
?
dTDP-4-amino-4,6-dideoxy-alpha-D-glucopyranose + S-adenosyl-L-methionine + reduced acceptor
dTDP-3-dehydro-4,6-dideoxy-alpha-D-glucopyranose + NH3 + L-methionine + 5'-deoxyadenosine + acceptor
key reaction in the biosynthesis of TDP-desosamine, which is an essential component of many macrolide antibiotics
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-
?
dTDP-4-amino-4,6-dideoxy-alpha-D-glucopyranose + S-adenosyl-L-methionine + reduced acceptor
dTDP-3-dehydro-4,6-dideoxy-alpha-D-glucopyranose + NH3 + L-methionine + 5'-deoxyadenosine + acceptor
the enzyme is involved in the biosynthesis of TDP-desosamine
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-
?
dTDP-4-amino-4,6-dideoxy-alpha-D-glucopyranose + S-adenosyl-L-methionine + reduced acceptor
dTDP-3-dehydro-4,6-dideoxy-alpha-D-glucopyranose + NH3 + L-methionine + 5'-deoxyadenosine + acceptor
a mechanism is proposed involving direct elimination of ammonium concerted with proton transfer to the nucleofuge from the adjacent alpha-hydroxyalkyl radical
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-
?
dTDP-4-amino-4,6-dideoxy-alpha-D-glucopyranose + S-adenosyl-L-methionine + reduced acceptor
dTDP-3-dehydro-4,6-dideoxy-alpha-D-glucopyranose + NH3 + L-methionine + 5'-deoxyadenosine + acceptor
the radical S-adenosylmethionine enzyme catalyzes the C4-deamination of TDP-4-amino-4,6-dideoxyglucose through a C3 radical intermediate. If the C4 amino group is replaced with a hydroxy group (to give TDP-quinovose), the hydroxy group at C3 is oxidized to a ketone with no C4-dehydration
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?
additional information
?
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anaerobic incubation of dTDP-3-keto-6-deoxy-D-glucose (i.e. dTDP-D-quinovose) or dTDP-3-amino-3,6-dideoxy-D-glucose with S-adenosyl-L-methionine and the reconstituted and reduced DesII leads to the formation of dTDP-3-dehydro-6-deoxy-D-glucose. No turnover of dTDP-D-fucose, which contains an axial hydroxyl group at C4, is observed
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?
additional information
?
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anaerobic incubation of dTDP-3-keto-6-deoxy-D-glucose (i.e. dTDP-D-quinovose) or dTDP-3-amino-3,6-dideoxy-D-glucose with S-adenosyl-L-methionine and the reconstituted and reduced DesII leads to the formation of dTDP-3-dehydro-6-deoxy-D-glucose. No turnover of dTDP-D-fucose, which contains an axial hydroxyl group at C4, is observed
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-
?
additional information
?
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when the enzyme is incubated with TDP-D-quinovose instead of the natural substrate dTDP-4-amino-4,6-dideoxy-D-glucopyranose, analogous elimination of the C4 hydroxyl is not observed - rather, the C3 hydroxyl is oxidized to the corresponding ketone. EPR characterization of a radical intermediate generated during its catalyzed dehydrogenation of TDP-D-Quinovose
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?
