Information on EC 2.4.1.B46 - 4-O-(alpha-L-rhodosaminyl)aklavinone L-2-deoxyfucosyltransferase

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The expected taxonomic range for this enzyme is: Streptomyces galilaeus

EC NUMBER
COMMENTARY hide
2.4.1.B46
preliminary BRENDA-supplied EC number
RECOMMENDED NAME
GeneOntology No.
4-O-(alpha-L-rhodosaminyl)aklavinone L-2-deoxyfucosyltransferase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
dTDP-2-deoxy-beta-L-fucose + 4-O-(alpha-L-rhodosaminyl)aklavinone = dTDP + 4-O-[(4-O-2-deoxy-alpha-L-fucosyl)-alpha-L-rhodosaminyl]aklavinone
show the reaction diagram
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SYSTEMATIC NAME
IUBMB Comments
dTDP-alpha-L-2-deoxyfucose:4-O-(alpha-L-rhodosaminyl)aklavinone L-2-deoxyfucosyltransferase
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
dTDP-2-deoxy-alpha-L-fucose + 4-O-[(4-O-2-deoxy-alpha-L-fucosyl)-alpha-L-rhodosaminyl]aklavinone
dTDP + 4-O-[[4-O-2-deoxy-alpha-L-fucosyl-(4-O-alpha-L-2-deoxyfucosyl)]alpha-L-rhodosaminyl]aklavinone
show the reaction diagram
AknK also catalyzes a tandem addition of a second L-2-deoxyfucosyl moiety, albeit with reduced activity, to the natural disaccharide chain to produce L-deoxyfucosyl-L-deoxyfucosyl-L-rhodosaminyl aklavinone, a variant of the natural aclacinomycin A. The second transfer reaction is 3 orders of magnitude slower than the first sugar transfer reaction catalyzed by AknK
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?
dTDP-2-deoxy-alpha-L-fucose + 4-O-[(4-O-2-deoxy-alpha-L-fucosyl)-alpha-L-rhodosaminyl]aklavinone
dTDP + 4-O-[[4-O-alpha-L-2-deoxyfucosyl-(4-O-2-deoxy-alpha-L-fucosyl)]alpha-L-rhodosaminyl]aklavinone
show the reaction diagram
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-
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-
?
dTDP-2-deoxy-alpha-L-fucose + idarubicin
dTDP + 4'-O-(2-deoxy-alpha-L-fucosyl)idarubicin
show the reaction diagram
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-
-
?
dTDP-2-deoxy-beta-L-fucose + 4-O-(alpha-L-rhodosaminyl)aklavinone
dTDP + 4-O-[(4-O-2-deoxy-alpha-L-fucosyl)-alpha-L-rhodosaminyl]aklavinone
show the reaction diagram
dTDP-L-daunosamine + 4-O-(alpha-L-rhodosaminyl)aklavinone
dTDP + 4-O-[(4-O-alpha-L-daunosaminyl)-alpha-L-rhodosaminyl]aklavinone
show the reaction diagram
the enzyme accepts L-daunosamine as an alternative sugar substrate, albeit with a 270fold decrease in catalytic efficiency (kcat/Km)
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?
additional information
?
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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
dTDP-2-deoxy-beta-L-fucose + 4-O-(alpha-L-rhodosaminyl)aklavinone
dTDP + 4-O-[(4-O-2-deoxy-alpha-L-fucosyl)-alpha-L-rhodosaminyl]aklavinone
show the reaction diagram
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.104 - 0.109
4-O-(alpha-L-rhodosaminyl)aklavinone
0.149 - 0.531
dTDP-2-deoxy-beta-L-fucose
0.94
dTDP-L-daunosamine
pH 7.5, 25C, cosubstrate: rhodosaminyl aklavinone
0.138
idarubicin
pH 7.5, 25C, cosubstrate: dTDP-alpha-L-2-deoxyfucose
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.33 - 5.7
4-O-(alpha-L-rhodosaminyl)aklavinone
19790
0.17 - 7.3
dTDP-2-deoxy-alpha-L-fucose
6399
0.037
dTDP-L-daunosamine
Streptomyces galilaeus
Q9L555
pH 7.5, 25C, cosubstrate: 4-O-(alpha-L-rhodosaminyl)aklavinone
42642
0.65
idarubicin
Streptomyces galilaeus
Q9L555
pH 7.5, 25C, cosubstrate: dTDP-2-deoxy-alpha-L-fucose
20307
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
65000
x * 65000, SDS-PAGE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
x * 65000, SDS-PAGE
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
subcloned into a pET-22b expression vector and expressed recombinantly in Escherichia coli as a C-terminal His6-tagged protein
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
synthesis
AknK may be a useful enzyme for the chemoenzymatic synthesis of anthracycline variants