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dTDP-6-deoxy-beta-L-mannose + N-acetyl-alpha-D-glucosaminyl-diphospho-trans,octacis-decaprenol = dTDP + alpha-L-rhamnopyranosyl-(1->3)-N-acetyl-alpha-D-glucosaminyl-diphospho-trans,octacis-decaprenol
dTDP-6-deoxy-beta-L-mannose + N-acetyl-alpha-D-glucosaminyl-diphospho-trans,octacis-decaprenol = dTDP + alpha-L-rhamnopyranosyl-(1->3)-N-acetyl-alpha-D-glucosaminyl-diphospho-trans,octacis-decaprenol
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dTDP-6-deoxy-beta-L-mannose + N-acetyl-alpha-D-glucosaminyl-diphospho-trans,octacis-decaprenol = dTDP + alpha-L-rhamnopyranosyl-(1->3)-N-acetyl-alpha-D-glucosaminyl-diphospho-trans,octacis-decaprenol
kinetic analysis shows that WbbL uses a ternary complex mechanism reaction
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dTDP-6-deoxy-beta-L-mannose + N-acetyl-alpha-D-glucosaminyl-diphospho-trans,octacis-decaprenol = dTDP + alpha-L-rhamnopyranosyl-(1->3)-N-acetyl-alpha-D-glucosaminyl-diphospho-trans,octacis-decaprenol
kinetic analysis shows that WbbL uses a ternary complex mechanism reaction
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dTDP-6-deoxy-beta-L-mannose + N-acetyl-alpha-D-glucosaminyl-diphospho-trans,octacis-decaprenol
dTDP + alpha-L-rhamnopyranosyl-(1->3)-N-acetyl-alpha-D-glucosaminyl-diphospho-trans,octacis-decaprenol
dTDP-beta-L-rhamnose + GlcNAc-diphospho-trans,octacis-decaprenol
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additional information
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dTDP-6-deoxy-beta-L-mannose + N-acetyl-alpha-D-glucosaminyl-diphospho-trans,octacis-decaprenol
dTDP + alpha-L-rhamnopyranosyl-(1->3)-N-acetyl-alpha-D-glucosaminyl-diphospho-trans,octacis-decaprenol
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dTDP-6-deoxy-beta-L-mannose + N-acetyl-alpha-D-glucosaminyl-diphospho-trans,octacis-decaprenol
dTDP + alpha-L-rhamnopyranosyl-(1->3)-N-acetyl-alpha-D-glucosaminyl-diphospho-trans,octacis-decaprenol
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dTDP-6-deoxy-beta-L-mannose + N-acetyl-alpha-D-glucosaminyl-diphospho-trans,octacis-decaprenol
dTDP + alpha-L-rhamnopyranosyl-(1->3)-N-acetyl-alpha-D-glucosaminyl-diphospho-trans,octacis-decaprenol
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dTDP-6-deoxy-beta-L-mannose + N-acetyl-alpha-D-glucosaminyl-diphospho-trans,octacis-decaprenol
dTDP + alpha-L-rhamnopyranosyl-(1->3)-N-acetyl-alpha-D-glucosaminyl-diphospho-trans,octacis-decaprenol
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natural acceptor substrate GlcNAc-P-P-decaprenyl
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dTDP-6-deoxy-beta-L-mannose + N-acetyl-alpha-D-glucosaminyl-diphospho-trans,octacis-decaprenol
dTDP + alpha-L-rhamnopyranosyl-(1->3)-N-acetyl-alpha-D-glucosaminyl-diphospho-trans,octacis-decaprenol
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dTDP-6-deoxy-beta-L-mannose + N-acetyl-alpha-D-glucosaminyl-diphospho-trans,octacis-decaprenol
dTDP + alpha-L-rhamnopyranosyl-(1->3)-N-acetyl-alpha-D-glucosaminyl-diphospho-trans,octacis-decaprenol
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natural acceptor substrate GlcNAc-P-P-decaprenyl
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dTDP-beta-L-rhamnose + GlcNAc-diphospho-trans,octacis-decaprenol
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dTDP-beta-L-rhamnose + GlcNAc-diphospho-trans,octacis-decaprenol
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additional information
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in vitro transfer of N,N'-diacetylbacillosamine phosphate onto Und-P and the in vitro enzymatic synthesis of the heptasacccharide using a chemically synthesized undecaprenyl diphosphate-linked N,N'-diacetylbacillosamine. The reactions of PglC, PglA, PglH, PglJ and PglI are coupled in a single reaction vessel, NMR spectrometric product analysis
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additional information
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in vitro, trisaccharide is prepared by using PglA and PglJ and then reacts singly with PglH
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additional information
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in vitro transfer of N,N'-diacetylbacillosamine phosphate onto Und-P and the in vitro enzymatic synthesis of the heptasacccharide using a chemically synthesized undecaprenyl diphosphate-linked N,N'-diacetylbacillosamine. The reactions of PglC, PglA, PglH, PglJ and PglI are coupled in a single reaction vessel, NMR spectrometric product analysis
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additional information
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in vitro, trisaccharide is prepared by using PglA and PglJ and then reacts singly with PglH
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dTDP-6-deoxy-beta-L-mannose + N-acetyl-alpha-D-glucosaminyl-diphospho-trans,octacis-decaprenol
dTDP + alpha-L-rhamnopyranosyl-(1->3)-N-acetyl-alpha-D-glucosaminyl-diphospho-trans,octacis-decaprenol
dTDP-6-deoxy-beta-L-mannose + N-acetyl-alpha-D-glucosaminyl-diphospho-trans,octacis-decaprenol
dTDP + alpha-L-rhamnopyranosyl-(1->3)-N-acetyl-alpha-D-glucosaminyl-diphospho-trans,octacis-decaprenol
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dTDP-6-deoxy-beta-L-mannose + N-acetyl-alpha-D-glucosaminyl-diphospho-trans,octacis-decaprenol
dTDP + alpha-L-rhamnopyranosyl-(1->3)-N-acetyl-alpha-D-glucosaminyl-diphospho-trans,octacis-decaprenol
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dTDP-6-deoxy-beta-L-mannose + N-acetyl-alpha-D-glucosaminyl-diphospho-trans,octacis-decaprenol
dTDP + alpha-L-rhamnopyranosyl-(1->3)-N-acetyl-alpha-D-glucosaminyl-diphospho-trans,octacis-decaprenol
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natural acceptor substrate GlcNAc-P-P-decaprenyl
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dTDP-6-deoxy-beta-L-mannose + N-acetyl-alpha-D-glucosaminyl-diphospho-trans,octacis-decaprenol
dTDP + alpha-L-rhamnopyranosyl-(1->3)-N-acetyl-alpha-D-glucosaminyl-diphospho-trans,octacis-decaprenol
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natural acceptor substrate GlcNAc-P-P-decaprenyl
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malfunction
the temperature-sensitive mc2155 strain 2-20/32 mutant shows loss of this transferase activity in 2-20/32 at elevated temperatures, complementation by expression of the enzyme encoded by genes wbbL from Escherichia coli and froms Mycobacterium tuberculosis
malfunction
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the temperature-sensitive mc2155 strain 2-20/32 mutant shows loss of this transferase activity in 2-20/32 at elevated temperatures, complementation by expression of the enzyme encoded by genes wbbL from Escherichia coli and froms Mycobacterium tuberculosis
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metabolism
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PglA is part of a general N-linked glycosylation pathway, encoded by the pgl gene cluster, which culminates in the transfer of a heptasaccharide: GalNAc-alpha1,4-GalNAc-alpha1,4-(Glcbeta1,3)-GalNAc-alpha1,4-GalNAc-alpha1,4-GalNAc-alpha1,3-Bac, where Bac is bacillosamine (2,4-diacetamido-2,4,6-trideoxyglucose), from a membrane-anchored undecaprenyldiphosphate-linked donor to the asparagine side chain of proteins at the Asn-X-Ser/Thr motif. The glycosyltransferases, PglA, PglH, PglI, and PglJ, responsible for the biosynthesis of the Und-PP-linked heptasaccharide. PglA adds the first GalNAc residue on to the isoprenoid-linked Bac carrier
metabolism
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the Pgl pathway produces the N-linked glycan heptasaccharide GalNAc-alpha1,4-GalNAc-alpha1,4-(Glcbeta1,3)-GalNAc-alpha1,4-GalNAc-alpha1,4-GalNAc-alpha1,3-Bac2,4diNAc-_1-Asn. The pathway begins with diphosphate bond formation between the Bac2,4diNAc phosphate and undecaprenylphosphate (Und-P) by Cj1124c (PglC) to form Bac2,4diNAc-alpha1-PP-Und. One N-acetylgalactosamine (GalNAc) is linked to the polyisoprenediphosphate-bound N,N'-diacetylbacillosamine by Cj1125c (PglA) to form GalNAc-alpha1,3-Bac2,4diNAc-alpha1-PP-Und. Next, four additional GalNAc and one branching glucose are added sequentially to the isoprene-linked disaccharide by PglJ, PglH, and PglI, to form the heptasaccharide, overview
metabolism
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the Pgl pathway produces the N-linked glycan heptasaccharide GalNAc-alpha1,4-GalNAc-alpha1,4-(Glcbeta1,3)-GalNAc-alpha1,4-GalNAc-alpha1,4-GalNAc-alpha1,3-Bac2,4diNAc-_1-Asn. The pathway begins with diphosphate bond formation between the Bac2,4diNAc phosphate and undecaprenylphosphate (Und-P) by Cj1124c (PglC) to form Bac2,4diNAc-alpha1-PP-Und. One N-acetylgalactosamine (GalNAc) is linked to the polyisoprenediphosphate-bound N,N'-diacetylbacillosamine by Cj1125c (PglA) to form GalNAc-alpha1,3-Bac2,4diNAc-alpha1-PP-Und. Next, four additional GalNAc and one branching glucose are added sequentially to the isoprene-linked disaccharide by PglJ, PglH, and PglI, to form the heptasaccharide, overview
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metabolism
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PglA is part of a general N-linked glycosylation pathway, encoded by the pgl gene cluster, which culminates in the transfer of a heptasaccharide: GalNAc-alpha1,4-GalNAc-alpha1,4-(Glcbeta1,3)-GalNAc-alpha1,4-GalNAc-alpha1,4-GalNAc-alpha1,3-Bac, where Bac is bacillosamine (2,4-diacetamido-2,4,6-trideoxyglucose), from a membrane-anchored undecaprenyldiphosphate-linked donor to the asparagine side chain of proteins at the Asn-X-Ser/Thr motif. The glycosyltransferases, PglA, PglH, PglI, and PglJ, responsible for the biosynthesis of the Und-PP-linked heptasaccharide. PglA adds the first GalNAc residue on to the isoprenoid-linked Bac carrier
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physiological function
the enzyme is required for the rhamnosyl-L-containing linker unit responsible for the attachment of the cell wall polymer mycolyl-arabinogalactan to the peptidoglycan in mycobacteria
physiological function
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WbbL catalyzes the transfer of an alpha-L-rhamnopyranose residue from dTDP-Rha to decaprenyldiphosphoryl-alpha-D-N-acetyl glucosamine, GlcNAc-P-PDP, to form alpha-L-Rhap-(1->3)-alpha-D-GlcNAc-P-P-DP, which is then further elongated with Galf and Araf units and finally mycolylated and attached to the peptidoglycan. The enzyme is essential for Mycobacterium tuberculosis viability and is absent in eukaryotic cells
physiological function
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gene RmlT is part of the rmlABCD locus encoding the biosynthetic pathway for L-rhamnose. Transferase RmlT is required for the incorporation of L-rhamnose into wall teichoic acids. Wall teichoic acids isolated from bacteria lacking RmlT display a faster migration in gel and do not contain any trace of L-rhamnose. The presence of L-rhamnosylated wall teichoic acids at the surface of Listeria monocytogenes delays the crossing of the cell wall by antimicrobial peptides and postpones their contact with the listerial membrane. Wall teichoic acids L-rhamnosylation promotes Listeri monocytogenes survival by decreasing the cell wall permeability to antimicrobial peptides, thus hindering their access and detrimental interaction with the plasma membrane
physiological function
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WbbL catalyzes the transfer of an alpha-L-rhamnopyranose residue from dTDP-Rha to decaprenyldiphosphoryl-alpha-D-N-acetyl glucosamine, GlcNAc-P-PDP, to form alpha-L-Rhap-(1->3)-alpha-D-GlcNAc-P-P-DP, which is then further elongated with Galf and Araf units and finally mycolylated and attached to the peptidoglycan. The enzyme is essential for Mycobacterium tuberculosis viability and is absent in eukaryotic cells
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physiological function
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the enzyme is required for the rhamnosyl-L-containing linker unit responsible for the attachment of the cell wall polymer mycolyl-arabinogalactan to the peptidoglycan in mycobacteria
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additional information
the Escherichia coli mutant strain K12 EMG2 contains an insertionally inactivated wbbL and is devoid of any O-antigen and shows no WbbL activity, complementation by expression of WbbL from Mycobacterium tuberculosis, a plasmid encoding the putative rhamnosyltransferase gene from Mycobacterium tuberculosis also results in O-antigen synthesis
additional information
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the Escherichia coli mutant strain K12 EMG2 contains an insertionally inactivated wbbL and is devoid of any O-antigen and shows no WbbL activity, complementation by expression of WbbL from Mycobacterium tuberculosis, a plasmid encoding the putative rhamnosyltransferase gene from Mycobacterium tuberculosis also results in O-antigen synthesis
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additional information
the temperature-sensitive mutant contains a single-base change that has a proline changed to a serine residue. Exposure of in mc2155 mutant 2-20/32 to higher non-permissive temperatures results in bacteria that cannot be recovered at the lower permissive temperatures. Complementation of the mutants strain by expression of gene wbbL from Escherichia coli or Mycobacterium tuberculosis
additional information
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the temperature-sensitive mutant contains a single-base change that has a proline changed to a serine residue. Exposure of in mc2155 mutant 2-20/32 to higher non-permissive temperatures results in bacteria that cannot be recovered at the lower permissive temperatures. Complementation of the mutants strain by expression of gene wbbL from Escherichia coli or Mycobacterium tuberculosis
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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, Campylobacter jejuni NCTC 11168
brenda
Mills, J.A.; Motichka, K.; Jucker, M.; Wu, H.P.; Uhlik, B.C.; Stern, R.J.; Scherman, M.S.; Vissa, V.D.; Pan, F.; Kundu, M.; Ma, Y.F.; McNeil, M.
Inactivation of the mycobacterial rhamnosyltransferase, which is needed for the formation of the arabinogalactan-peptidoglycan linker, leads to irreversible loss of viability
J. Biol. Chem.
279
43540-43546
2004
Escherichia coli (P36667), Mycobacterium tuberculosis (P9WMY3), Mycolicibacterium smegmatis (Q9RN49), Mycolicibacterium smegmatis mc(2)155 / ATCC 700084 (Q9RN49), Mycobacterium tuberculosis H37Rv (P9WMY3), Escherichia coli WG1 (P36667)
brenda
Grzegorzewicz, A.E.; Ma, Y.; Jones, V.; Crick, D.; Liav, A.; McNeil, M.R.
Development of a microtitre plate-based assay for lipid-linked glycosyltransferase products using the mycobacterial cell wall rhamnosyltransferase WbbL
Microbiology
154
3724-3730
2008
Mycobacterium tuberculosis, Mycobacterium tuberculosis H37Rv
brenda
Glover, K.J.; Weerapana, E.; Imperiali, B.
In vitro assembly of the undecaprenylpyrophosphate-linked heptasaccharide for prokaryotic N-linked glycosylation
Proc. Natl. Acad. Sci. USA
102
14255-14259
2005
Campylobacter jejuni, Campylobacter jejuni NCTC 11168
brenda
Carvalho, F.; Atilano, M.L.; Pombinho, R.; Covas, G.; Gallo, R.L.; Filipe, S.R.; Sousa, S.; Cabanes, D.
L-Rhamnosylation of Listeria monocytogenes wall teichoic acids promotes resistance to antimicrobial peptides by delaying interaction with the membrane
PLoS Pathog.
11
e1004919
2015
Listeria monocytogenes
brenda