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Information on EC 2.4.1.310 - vancomycin aglycone glucosyltransferase
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2.4.1.310 vancomycin aglycone glucosyltransferaseIUBMB Comments
The enzyme from the bacterium Amycolatopsis orientalis is involved in the biosynthesis of the glycopeptide antibiotic chloroeremomycin.
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The enzyme appears in viruses and cellular organisms
Synonyms
GtfB, GtfE, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
GtfB
GtfE
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
UDP-alpha-D-glucose + vancomycin aglycone = UDP + devancosaminyl-vancomycin
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
UDP-alpha-D-glucose:vancomycin aglycone 48-O-beta-D-glucosyltransferase
The enzyme from the bacterium Amycolatopsis orientalis is involved in the biosynthesis of the glycopeptide antibiotic chloroeremomycin.
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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
UDP-alpha-D-glucose + teicoplanin aglycone
UDP + ?
very low glucosylation activity
-
-
?
UDP-alpha-D-glucose + teicoplanin aglycone
UDP + ?
very low glucosylation activity
-
-
?
UDP-alpha-D-glucose + vancomycin aglycone
UDP + devancoaminyl vancomycin
-
-
-
-
?
UDP-alpha-D-glucose + vancomycin aglycone
UDP + devancoaminyl vancomycin
-
-
-
?
UDP-alpha-D-glucose + vancomycin aglycone
UDP + devancoaminyl vancomycin
the enzyme is involved in the biosynthesis of chloroeremomycin
-
-
?
UDP-alpha-D-glucose + vancomycin aglycone
UDP + devancoaminyl vancomycin
the enzyme is involved in the biosynthesis of the glycopeptide antibiotic chloroeremomycin
-
-
?
UDP-alpha-D-glucose + vancomycin aglycone
UDP + devancoaminyl vancomycin
the enzyme transfers the glucose residue from UDP-glucose to the 4-OH-PheGly4 residue of the vancomycin aglycone
-
-
?
UDP-alpha-D-glucose + vancomycin aglycone
UDP + devancoaminyl vancomycin
the enzyme is involved in the biosynthesis of the glycopeptide antibiotic chloroeremomycin
-
-
?
UDP-alpha-D-glucose + vancomycin aglycone
UDP + devancoaminyl vancomycin
the enzyme transfers the glucose residue from UDP-glucose to the 4-OH-PheGly4 residue of the vancomycin aglycone
-
-
?
UDP-alpha-D-glucose + vancomycin aglycone
UDP + devancoaminyl vancomycin
-
-
-
?
UDP-alpha-D-glucose + vancomycin aglycone
UDP + devancoaminyl vancomycin
the enzyme is involved in the biosynthesis of chloroeremomycin
-
-
?
UDP-alpha-D-glucose + vancomycin aglycone
UDP + devancoaminyl vancomycin
-
-
-
-
?
additional information
?
-
-
study on reaction after modification of the vancomycin aglycon. Modification at the N-terminus amine of vancomycin aglycon is well tolerated, whereas C-terminus modification with removal of the acidic carboxylic acid results in a slower, less effective initial glycosylation
-
-
?
additional information
?
-
-
study on reaction after modification of the vancomycin aglycon. Modification at the N-terminus amine of vancomycin aglycon is well tolerated, whereas C-terminus modification with removal of the acidic carboxylic acid results in a slower, less effective initial glycosylation
-
-
?
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NATURAL SUBSTRATE
NATURAL 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
UDP-alpha-D-glucose + vancomycin aglycone
UDP + devancoaminyl vancomycin
the enzyme is involved in the biosynthesis of chloroeremomycin
-
-
?
UDP-alpha-D-glucose + vancomycin aglycone
UDP + devancoaminyl vancomycin
the enzyme is involved in the biosynthesis of the glycopeptide antibiotic chloroeremomycin
-
-
?
UDP-alpha-D-glucose + vancomycin aglycone
UDP + devancoaminyl vancomycin
the enzyme is involved in the biosynthesis of the glycopeptide antibiotic chloroeremomycin
-
-
?
UDP-alpha-D-glucose + vancomycin aglycone
UDP + devancoaminyl vancomycin
the enzyme is involved in the biosynthesis of chloroeremomycin
-
-
?
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.45
UDP-alpha-D-glucose
mutant enzyme H125A, pH and temperature not specified in the publication
1.1
UDP-alpha-D-glucose
mutant enzyme D13A, pH and temperature not specified in the publication
1.3
UDP-alpha-D-glucose
wild-type enzyme, pH and temperature not specified in the publication
3.3
UDP-alpha-D-glucose
mutant enzyme D332A, pH and temperature not specified in the publication
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0022
UDP-alpha-D-glucose
mutant enzyme D332A, pH and temperature not specified in the publication
0.043
UDP-alpha-D-glucose
mutant enzyme D13A, pH and temperature not specified in the publication
0.55
UDP-alpha-D-glucose
wild-type enzyme, pH and temperature not specified in the publication
0.72
UDP-alpha-D-glucose
mutant enzyme H125A, pH and temperature not specified in the publication
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.00067
UDP-alpha-D-glucose
mutant enzyme D332A, pH and temperature not specified in the publication
0.039
UDP-alpha-D-glucose
mutant enzyme D13A, pH and temperature not specified in the publication
0.42
UDP-alpha-D-glucose
wild-type enzyme, pH and temperature not specified in the publication
1.6
UDP-alpha-D-glucose
mutant enzyme H125A, pH and temperature not specified in the publication
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
physiological function
physiological function
the enzyme is involved in the biosynthesis of chloroeremomycin
physiological function
-
the enzyme is involved in the biosynthesis of chloroeremomycin
-
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). A0A7W7LNA0_9ACTN
404
0
42078
TrEMBL
-
A0A7W3MVB9_9ACTN
407
0
42756
TrEMBL
-
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
44000
x * 44000, C-terminal His6-tagged version of GtfB, SDS-PAGE
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
?
x * 44000, C-terminal His6-tagged version of GtfB, SDS-PAGE
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CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANIC SOLVENT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
DMSO
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli as a hexahistidine-tagged protein
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
synthesis
synthesis
-
in vitro sequential glycosylations of the vancomycin aglycon catalyzed by the glycosyltransferases GtfE and GtfD and total synthesis of vancomycin and derivatives. For GtfE, presence of reductant tris(2-carboxyethyl)phosphine (TCEP, 2 mM) is crucial
synthesis
-
in vitro sequential glycosylations of the vancomycin aglycon catalyzed by the glycosyltransferases GtfE and GtfD and total synthesis of vancomycin and derivatives. For GtfE, presence of reductant tris(2-carboxyethyl)phosphine (TCEP, 2 mM) is crucial
-
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Mulichak, A.M.; Losey, H.C.; Walsh, C.T.; Garavito, R.M.
Structure of the UDP-glucosyltransferase GtfB that modifies the heptapeptide aglycone in the biosynthesis of vancomycin group antibiotics
Structure
9
547-557
2001
Amycolatopsis orientalis (P96559), Amycolatopsis orientalis A82846 (P96559)
brenda
Losey, H.C.; Peczuh, M.W.; Chen, Z.; Eggert, U.S.; Dong, S.D.; Pelczer, I.; Kahne, D.; Walsh, C.T.
Tandem action of glycosyltransferases in the maturation of vancomycin and teicoplanin aglycones: novel glycopeptides
Biochemistry
40
4745-4755
2001
Amycolatopsis orientalis (P96559), Amycolatopsis orientalis A82846 (P96559)
brenda
Nakayama, A.; Okano, A.; Feng, Y.; Collins, J.C.; Collins, K.C.; Walsh, C.T.; Boger, D.L.
Enzymatic glycosylation of vancomycin aglycon: completion of a total synthesis of vancomycin and N- and C-terminus substituent effects of the aglycon substrate
Org. Lett.
16
3572-3575
2014
Amycolatopsis orientalis, Amycolatopsis orientalis ATCC 19795
brenda
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