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Information on EC 2.1.1.234 - dTDP-3-amino-3,4,6-trideoxy-alpha-D-glucopyranose N,N-dimethyltransferase and Organism(s) Streptomyces venezuelae and UniProt Accession Q9ZGH6

for references in articles please use BRENDA:EC2.1.1.234
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IUBMB Comments
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.
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This record set is specific for:
Streptomyces venezuelae
UNIPROT: Q9ZGH6
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The taxonomic range for the selected organisms is: Streptomyces venezuelae
The expected taxonomic range for this enzyme is: Bacteria, Archaea
Synonyms
desvi, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
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.
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
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
-
-
?
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
the enzyme is involved in the biosynthesis of desosamine
-
-
?
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 SUBSTRATE
NATURAL 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-4,6-dideoxy-alpha-D-glucopyranose
2 S-adenosyl-L-homocysteine + dTDP-3-dimethylamino-4,6-dideoxy-alpha-D-glucopyranose
show the reaction diagram
the enzyme is involved in the biosynthesis of desosamine
-
-
?
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
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.3074
dTDP-3-amino-3,4,6-trideoxy-alpha-D-glucose
pH 7.5, 24°C, cosubstrate: 3.0 mM S-adenosyl-L-methionine
0.2766
dTDP-3-amino-3,6-dideoxy-alpha-D-glucopyranose
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
pH 7.5, 24°C, cosubstrate: 3.0 mM S-adenosyl-L-methionine
0.07
dTDP-3-amino-3,6-dideoxy-alpha-D-glucopyranose
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
pH 7.5, 24°C, cosubstrate: 3.0 mM S-adenosyl-L-methionine
0.25
dTDP-3-amino-3,6-dideoxy-alpha-D-glucopyranose
pH 7.5, 24°C, cosubstrate: 3.0 mM S-adenosyl-L-methionine
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
the enzyme catalyzes the N,N-dimethylation step in the biosynthesis of desosamine
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
DESVI_STRVZ
237
0
25979
Swiss-Prot
-
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
28000
2 * 28000, SDS-PAGE
47400
gel filtration
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dimer
homodimer
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
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
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
enzyme tagged with His6 at the N-terminus
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Chang, C.w.; Zhao, L.; Yamase, H., Liu, H.w.
DesVI: A new member of the sugar N,N-dimethyltransferase family involved in the biosynthesis of desosamine
Angew. Chem. Int. Ed. Engl.
39
2160-2163
2000
Streptomyces venezuelae (Q9ZGH6)
Manually annotated by BRENDA team
Chen, H.; Yamase, H.; Murakami, K.; Chang, C.W.; Zhao, L.; Zhao, Z.; Liu, H.W.
Expression, purification, and characterization of two N,N-dimethyltransferases, tylM1 and desVI, involved in the biosynthesis of mycaminose and desosamine
Biochemistry
41
9165-9183
2002
Streptomyces venezuelae (Q9ZGH6)
Manually annotated by BRENDA team
Burgie, E.S.; Holden, H.M.
Three-dimensional structure of DesVI from Streptomyces venezuelae: a sugar N,N-dimethyltransferase required for dTDP-desosamine biosynthesis
Biochemistry
47
3982-3988
2008
Streptomyces venezuelae (Q9ZGH6), Streptomyces venezuelae
Manually annotated by BRENDA team