Information on EC 2.1.1.234 - dTDP-3-amino-3,4,6-trideoxy-alpha-D-glucopyranose N,N-dimethyltransferase

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The expected taxonomic range for this enzyme is: Streptomyces venezuelae

EC NUMBER
COMMENTARY hide
2.1.1.234
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RECOMMENDED NAME
GeneOntology No.
dTDP-3-amino-3,4,6-trideoxy-alpha-D-glucopyranose N,N-dimethyltransferase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
2 S-adenosyl-L-methionine + dTDP-3-amino-3,4,6-trideoxy-alpha-D-glucopyranose = 2 S-adenosyl-L-homocysteine + dTDP-3-dimethylamino-3,4,6-trideoxy-alpha-D-glucopyranose
show the reaction diagram
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Biosynthesis of antibiotics
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dTDP-D-desosamine biosynthesis
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Polyketide sugar unit biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
S-adenosyl-L-methionine:dTDP-3-amino-3,4,6-trideoxy-alpha-D-glucopyranose 3-N,N-dimethyltransferase
The enzyme is involved in the biosynthesis of desosamine, a 3-(dimethylamino)-3,4,6-trideoxyhexose found in certain macrolide antibiotics such as erthyromycin, azithromycin, and clarithromycin.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
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the enzyme catalyzes the N,N-dimethylation step in the biosynthesis of desosamine
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
2 S-adenosyl-L-methionine + dTDP-3-amino-3,6-dideoxy-alpha-D-glucopyranose
2 S-adenosyl-L-homocysteine + dTDP-3-dimethylamino-3,6-dideoxy-alpha-D-glucopyranose
show the reaction diagram
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the kcat/KM for dTDP-3-amino-3,6-dideoxy-alpha-D-glucopyranose is about 20fold lower than kcat/Km for the natural substrated TDP-3-amino-4,6-dideoxy-alpha-D-glucopyranose
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-
?
2 S-adenosyl-L-methionine + dTDP-3-amino-4,6-dideoxy-alpha-D-glucopyranose
2 S-adenosyl-L-homocysteine + dTDP-3-dimethylamino-4,6-dideoxy-alpha-D-glucopyranose
show the reaction diagram
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the enzyme is involved in the biosynthesis of desosamine
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-
?
2 S-adenosyl-L-methionine + TDP-3-amino-4,6-dideoxy-alpha-D-glucopyranose
2 S-adenosyl-L-homocysteine + dTDP-3-dimethylamino-4,6-dideoxy-alpha-D-glucopyranose
show the reaction diagram
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
2 S-adenosyl-L-methionine + dTDP-3-amino-4,6-dideoxy-alpha-D-glucopyranose
2 S-adenosyl-L-homocysteine + dTDP-3-dimethylamino-4,6-dideoxy-alpha-D-glucopyranose
show the reaction diagram
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the enzyme is involved in the biosynthesis of desosamine
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-
?
2 S-adenosyl-L-methionine + TDP-3-amino-4,6-dideoxy-alpha-D-glucopyranose
2 S-adenosyl-L-homocysteine + dTDP-3-dimethylamino-4,6-dideoxy-alpha-D-glucopyranose
show the reaction diagram
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
S-adenosyl-L-methionine
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.3074
dTDP-3-amino-3,4,6-trideoxy-alpha-D-glucose
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pH 7.5, 24°C, cosubstrate: 3.0 mM S-adenosyl-L-methionine
0.2766
dTDP-3-amino-3,6-dideoxy-alpha-D-glucopyranose
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pH 7.5, 24°C, cosubstrate: 3.0 mM S-adenosyl-L-methionine
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1.533
dTDP-3-amino-3,4,6-trideoxy-alpha-D-glucose
Streptomyces venezuelae
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pH 7.5, 24°C, cosubstrate: 3.0 mM S-adenosyl-L-methionine
0.07
dTDP-3-amino-3,6-dideoxy-alpha-D-glucopyranose
Streptomyces venezuelae
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pH 7.5, 24°C, cosubstrate: 3.0 mM S-adenosyl-L-methionine
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
5
dTDP-3-amino-3,4,6-trideoxy-alpha-D-glucose
Streptomyces venezuelae
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pH 7.5, 24°C, cosubstrate: 3.0 mM S-adenosyl-L-methionine
19512
0.25
dTDP-3-amino-3,6-dideoxy-alpha-D-glucopyranose
Streptomyces venezuelae
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pH 7.5, 24°C, cosubstrate: 3.0 mM S-adenosyl-L-methionine
4448
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
28000
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2 * 28000, SDS-PAGE
28100
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2 * 28100
47400
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gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
homodimer
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2 * 28000, SDS-PAGE; 2 * 28110, calculated from sequence
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
hanging drop method of vapor diffusion method, X-ray crystal structure determined to 2.0 A resolution of DesVI complexed with S-adenosylmethionine and the substrate analogue UDP-benzene
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GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
inclusion of 0.1 mM S-adenosyl-L-methionine, 0.1 mM dithiothreitol, and 10% glycerol in in buffers is crucial to prevent TylM1 from precipitating during the purification
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
enzyme tagged with His6 at the N-terminus
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli