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Information on EC 4.2.1.135 - UDP-N-acetylglucosamine 4,6-dehydratase (configuration-retaining)
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4.2.1.135 UDP-N-acetylglucosamine 4,6-dehydratase (configuration-retaining)IUBMB Comments
Contains NAD+ as a cofactor . This is the first enzyme in the biosynthetic pathway of N,N'-diacetylbacillosamine , the first carbohydrate in the glycoprotein N-linked heptasaccharide in Campylobacter jejuni. This enzyme belongs to the short-chain dehydrogenase/reductase family of enzymes.
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The expected taxonomic range for this enzyme is: Bacteria, Archaea
Reaction Schemes
Synonyms
cj1120c, udp-n-acetylglucosamine c4,6-dehydratase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
Bc3750
BC_3750
Pdeg
PglF
UDP-Glc-NAc 4,6-dehydratase
UDP-N-acetylglucosamine C4,6-dehydratase
PglF
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-
-
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UDP-Glc-NAc 4,6-dehydratase
Bacillus cereus ATCC 14579 / DSM 31 / JCM 2152 / NBRC 15305 / NCIMB 9373 / NRRL B-3711
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UDP-N-acetylglucosamine C4,6-dehydratase
Bacillus cereus ATCC 14579 / DSM 31 / JCM 2152 / NBRC 15305 / NCIMB 9373 / NRRL B-3711
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-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
UDP-N-acetyl-alpha-D-glucosamine = UDP-2-acetamido-2,6-dideoxy-alpha-D-xylo-hex-4-ulose + H2O
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
UDP-N-acetyl-alpha-D-glucosamine hydro-lyase (configuration-retaining; UDP-2-acetamido-2,6-dideoxy-alpha-D-xylo-hex-4-ulose-forming)
Contains NAD+ as a cofactor [2]. This is the first enzyme in the biosynthetic pathway of N,N'-diacetylbacillosamine [1], the first carbohydrate in the glycoprotein N-linked heptasaccharide in Campylobacter jejuni. This enzyme belongs to the short-chain dehydrogenase/reductase family of enzymes.
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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-N-acetyl-alpha-D-glucosamine
UDP-2-acetamido-2,6-dideoxy-alpha-D-xylo-hex-4-ulose + H2O
UDP-N-acetylglucosamine
UDP-2-acetamido-2,6-dideoxy-alpha-D-4-ketohexulose + H2O
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-
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-
?
UDP-N-acetyl-alpha-D-glucosamine
UDP-2-acetamido-2,6-dideoxy-alpha-D-xylo-hex-4-ulose + H2O
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-
-
?
UDP-N-acetyl-alpha-D-glucosamine
UDP-2-acetamido-2,6-dideoxy-alpha-D-xylo-hex-4-ulose + H2O
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-
-
-
?
UDP-N-acetyl-alpha-D-glucosamine
UDP-2-acetamido-2,6-dideoxy-alpha-D-xylo-hex-4-ulose + H2O
Bacillus cereus ATCC 14579 / DSM 31 / JCM 2152 / NBRC 15305 / NCIMB 9373 / NRRL B-3711
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-
-
?
UDP-N-acetyl-alpha-D-glucosamine
UDP-2-acetamido-2,6-dideoxy-alpha-D-xylo-hex-4-ulose + H2O
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PglF performs a cofactor-dependent hydride transfer from the C4 position of UDP-GlcNAc to C6, in conjunction with the elimination of water across the glucosyl C5 and C6 bond
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?
additional information
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product identification by mass spectrometry and one- and two-dimensional NMR analysis, substrate specificity analysis, overview. None of the UDP-sugars tested including UDP-galactose, UDPGalNAc, UDP-GlcNAc, and UDP-glucose are substrates for recombinant Pdeg
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-
?
additional information
?
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Bacillus cereus ATCC 14579 / DSM 31 / JCM 2152 / NBRC 15305 / NCIMB 9373 / NRRL B-3711
product identification by mass spectrometry and one- and two-dimensional NMR analysis, substrate specificity analysis, overview. None of the UDP-sugars tested including UDP-galactose, UDPGalNAc, UDP-GlcNAc, and UDP-glucose are substrates for recombinant Pdeg
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?
additional information
?
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PglF catalyzes the formation of a UDP-4-oxo sugar with the appropriate stereochemistry at position 5'' from UDP-GlcNAc. Sugar capsule capsular polysaccharide A (CPSA), which coats the surface of the mammalian symbiont Bacteroides fragilis, is a key mediator of mammalian immune system development, the enzyme, coupled to a Bacteroides fragilis-encoded aminotransferase (WcfR), is used in sythetic construction system for CPSA for synthesis of the rare stereoconfiguration sugar acetamido-4-amino-6-deoxygalactopyranose in a two-step coupled reaction with WcfR, overview
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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-N-acetyl-alpha-D-glucosamine
UDP-2-acetamido-2,6-dideoxy-alpha-D-xylo-hex-4-ulose + H2O
UDP-N-acetyl-alpha-D-glucosamine
UDP-2-acetamido-2,6-dideoxy-alpha-D-xylo-hex-4-ulose + H2O
-
-
-
?
UDP-N-acetyl-alpha-D-glucosamine
UDP-2-acetamido-2,6-dideoxy-alpha-D-xylo-hex-4-ulose + H2O
Bacillus cereus ATCC 14579 / DSM 31 / JCM 2152 / NBRC 15305 / NCIMB 9373 / NRRL B-3711
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-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
NAD+
-
catalytic activity by GST-PglF is enhanced in the presence of additional NAD+ but not NADP+
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.118
UDP-N-acetyl-alpha-D-glucosamine
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pH 7.7, 37°C, full-length GST-PglF
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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
Bacillus cereus ATCC 14579 / DSM 31 / JCM 2152 / NBRC 15305 / NCIMB 9373 / NRRL B-3711
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UniProt
brenda
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
metabolism
physiological function
metabolism
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PglF is found to possess only C6 dehydratase activity generating UDP-2-acetamido-2,6-dideoxy-alpha-D-4-ketohexulose
metabolism
the enzme is involved in the biosynthesis of Bacillus glycans and N-acetylquinovosamine (2-acetamido-2,6-di-deoxy-D-glucose, QuiNAc)
metabolism
Bacillus cereus ATCC 14579 / DSM 31 / JCM 2152 / NBRC 15305 / NCIMB 9373 / NRRL B-3711
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the enzme is involved in the biosynthesis of Bacillus glycans and N-acetylquinovosamine (2-acetamido-2,6-di-deoxy-D-glucose, QuiNAc)
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metabolism
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PglF is found to possess only C6 dehydratase activity generating UDP-2-acetamido-2,6-dideoxy-alpha-D-4-ketohexulose
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physiological function
gene Pdeg encodes an UDP-N-acetylglucosamine C4,6-dehydratase that converts UDP-GlcNAc to UDP-4-keto-4,6-D-deoxy-GlcNAc (UDP-2-acetamido-2,6-dideoxy-alpha-D-xylo-4-hexulose). The product is then catalyzed by Preq-encoded UDP-4-reductase that converts UDP-4-keto-4,6-d-deoxy-GlcNAc to UDP-N-acetylquinovosamine
physiological function
Bacillus cereus ATCC 14579 / DSM 31 / JCM 2152 / NBRC 15305 / NCIMB 9373 / NRRL B-3711
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gene Pdeg encodes an UDP-N-acetylglucosamine C4,6-dehydratase that converts UDP-GlcNAc to UDP-4-keto-4,6-D-deoxy-GlcNAc (UDP-2-acetamido-2,6-dideoxy-alpha-D-xylo-4-hexulose). The product is then catalyzed by Preq-encoded UDP-4-reductase that converts UDP-4-keto-4,6-d-deoxy-GlcNAc to UDP-N-acetylquinovosamine
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Show AA Sequence and Transmembrane Helices (1082 entries)
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Please use the AA Sequence and Transmembrane Helices Search for a specific query.
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
monomer
monomer
Bacillus cereus ATCC 14579 / DSM 31 / JCM 2152 / NBRC 15305 / NCIMB 9373 / NRRL B-3711
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1 * 38000, recombinant His6-tagged enzyme, SDS-PAGE
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
DELTA1-129
additional information
DELTA1-129
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a truncated form of pglF coding for residues M130-V590 is generated omitting the transmembrane domain which expressed well in Escherichia coli. Substrate turnover is not observed in a reaction coupling the deletion construct DELTA1-129 and PglE suggesting the involvement of the PglF transmembrane domain in preventing the inhibitory reaction
DELTA1-129
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a truncated form of pglF coding for residues M130-V590 is generated omitting the transmembrane domain which expressed well in Escherichia coli. Substrate turnover is not observed in a reaction coupling the deletion construct DELTA1-129 and PglE suggesting the involvement of the PglF transmembrane domain in preventing the inhibitory reaction
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additional information
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four genes, Pdeg (UDP-N-acetylglucosamine C4,6-dehydratase), Preq (UDP-4-reductase), UDP-GlcNAc 6-DH (UDP-N-acetylglucosamine 6-dehydrogenase), and UXNAcS (UDP-N-acetylxylosamine synthase), are employed to synthesize UDP-quinovosamine, UDP-N-acetylglucosaminuronic acid, and UDP-N-acetylxylosamine in Escherichia coli. Escherichia coli nucleotide sugar biosynthetic pathway is engineered to increase the pool of substrate for the target nucleotide sugars. Uridine diphosphate dependent glycosyltransferase (UGT) is also selected and introduced into Escherichia coli. High levels of three novel flavonoid glycosides are obtained in the engineered mutant with 158.3 mg/l quercetin 3-O-(N-acetyl) quinovosamine, 172.5 mg/l luteolin 7-O-(N-acetyl)glucosaminuronic acid, and 160.8 mg/l quercetin 3-O-(N-acetyl)xylosamine
additional information
four genes, Pdeg (UDP-N-acetylglucosamine C4,6-dehydratase), Preq (UDP-4-reductase), UDP-GlcNAc 6-DH (UDP-N-acetylglucosamine 6-dehydrogenase), and UXNAcS (UDP-N-acetylxylosamine synthase), are employed to synthesize UDP-quinovosamine, UDP-N-acetylglucosaminuronic acid, and UDP-N-acetylxylosamine in Escherichia coli. Escherichia coli nucleotide sugar biosynthetic pathway is engineered to increase the pool of substrate for the target nucleotide sugars. Uridine diphosphate dependent glycosyltransferase (UGT) is also selected and introduced into Escherichia coli. High levels of three novel flavonoid glycosides are obtained in the engineered mutant with 158.3 mg/l quercetin 3-O-(N-acetyl) quinovosamine, 172.5 mg/l luteolin 7-O-(N-acetyl)glucosaminuronic acid, and 160.8 mg/l quercetin 3-O-(N-acetyl)xylosamine
additional information
Bacillus cereus ATCC 14579 / DSM 31 / JCM 2152 / NBRC 15305 / NCIMB 9373 / NRRL B-3711
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four genes, Pdeg (UDP-N-acetylglucosamine C4,6-dehydratase), Preq (UDP-4-reductase), UDP-GlcNAc 6-DH (UDP-N-acetylglucosamine 6-dehydrogenase), and UXNAcS (UDP-N-acetylxylosamine synthase), are employed to synthesize UDP-quinovosamine, UDP-N-acetylglucosaminuronic acid, and UDP-N-acetylxylosamine in Escherichia coli. Escherichia coli nucleotide sugar biosynthetic pathway is engineered to increase the pool of substrate for the target nucleotide sugars. Uridine diphosphate dependent glycosyltransferase (UGT) is also selected and introduced into Escherichia coli. High levels of three novel flavonoid glycosides are obtained in the engineered mutant with 158.3 mg/l quercetin 3-O-(N-acetyl) quinovosamine, 172.5 mg/l luteolin 7-O-(N-acetyl)glucosaminuronic acid, and 160.8 mg/l quercetin 3-O-(N-acetyl)xylosamine
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TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
recombinant His6-tagged enzyme from Escherichia coli by nickel affinity chromatography
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
gene Bc3750, sequence comparisons, recombinant expression of His6-tagged enzyme in Escherichia coli
gene Pdeg or pglF, recombinant expression in Escherichia coli, coexpression with Preq (UDP-4-reductase), UDP-GlcNAc 6-DH (UDP-N-acetylglucosamine 6-dehydrogenase), and UXNAcS (UDP-N-acetylxylosamine synthase), leading to biosynthesis of flavonoid glycosides in the engineered Escherichia coli strain, overview
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
biotechnology
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assay targets enzymes involved in the biosynthesis of the unusual bacterial sugar diNAcBac and the transfer of diNAcBac-phosphate to UndP. This multienzyme assay, together with the established assays for the individual enzymes, can be used to screen for inhibitors, and may be used to evaluate substrate flux along the inhibited pathway. This assay is optimized for maximum sensitivity to inhibition of PglF, PglE, PglD, and PglC by balancing the enzyme concentrations such that each is partially rate determining
synthesis
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sugar capsule capsular polysaccharide A (CPSA), which coats the surface of the mammalian symbiont Bacteroides fragilis, is a key mediator of mammalian immune system development, the enzyme, coupled to a Bacteroides fragilis-encoded aminotransferase (WcfR), is used in sythetic construction system for CPSA for synthesis of the rare stereoconfiguration sugar acetamido-4-amino-6-deoxygalactopyranose in a two-step coupled reaction with WcfR, overview
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Schoenhofen, I.C.; McNally, D.J.; Vinogradov, E.; Whitfield, D.; Young, N.M.; Dick, S.; Wakarchuk, W.W.; Brisson, J.R.; Logan, S.M.
Functional characterization of dehydratase/aminotransferase pairs from Helicobacter and Campylobacter: enzymes distinguishing the pseudaminic acid and bacillosamine biosynthetic pathways
J. Biol. Chem.
281
723-732
2006
Campylobacter jejuni
brenda
Olivier, N.B.; Chen, M.M.; Behr, J.R.; Imperiali, B.
In vitro biosynthesis of UDP-N,N'-diacetylbacillosamine by enzymes of the Campylobacter jejuni general protein glycosylation system
Biochemistry
45
13659-13669
2006
Campylobacter jejuni
brenda
Morrison, J.P.; Troutman, J.M.; Imperiali, B.
Development of a multicomponent kinetic assay of the early enzymes in the Campylobacter jejuni N-linked glycosylation pathway
Bioorg. Med. Chem.
18
8167-8171
2010
Campylobacter jejuni
brenda
Mostafavi, A.Z.; Troutman, J.M.
Biosynthetic assembly of the Bacteroides fragilis capsular polysaccharide A precursor bactoprenyl diphosphate-linked acetamido-4-amino-6-deoxygalactopyranose
Biochemistry
52
1939-1949
2013
Campylobacter jejuni
brenda
Cho, A.; Lee, S.; Kim, B.; Ahn, J.
Biosynthesis of three N-acetylaminosugar-conjugated flavonoids using engineered Escherichia coli
Microb. Cell Fact.
15
182
2016
Bacillus cereus, Bacillus cereus (Q81A42), Bacillus cereus ATCC 14579, Bacillus cereus ATCC 14579 / DSM 31 / JCM 2152 / NBRC 15305 / NCIMB 9373 / NRRL B-3711 (Q81A42)
brenda
Hwang, S.; Aronov, A.; Bar-Peled, M.
The biosynthesis of UDP-D-QuiNAc in Bacillus cereus ATCC 14579
PLoS ONE
10
e133790
2015
Bacillus cereus (Q81A42), Bacillus cereus ATCC 14579 / DSM 31 / JCM 2152 / NBRC 15305 / NCIMB 9373 / NRRL B-3711 (Q81A42)
brenda
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Release 2023.1 (January 2023)
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