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Enzyme Nomenclature
Information on EC 2.4.1.227 - undecaprenyldiphospho-muramoylpentapeptide beta-N-acetylglucosaminyltransferase
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The enzyme appears in viruses and cellular organisms
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EC NUMBER 
COMMENTARY 
2.4.1.227
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RECOMMENDED NAME
GeneOntology No.
undecaprenyldiphospho-muramoylpentapeptide beta-N-acetylglucosaminyltransferase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
UDP-N-acetylglucosamine + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol = UDP + GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
UDP-N-acetylglucosamine + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol = UDP + GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
MurG utilizes an ordered Bi Bi mechanism in which the donor binds first
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UDP-N-acetylglucosamine + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol = UDP + GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
transfer of alpha-N-acetylglucosamine
transfer of alpha-N-acetylglucosamine
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
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SYSTEMATIC NAME
IUBMB Comments
UDP-N-acetyl-D-glucosamine:N-acetyl-alpha-D-muramyl(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol 4-beta-N-acetylglucosaminlytransferase
The enzyme also works when the lysine residue is replaced by meso-2,6-diaminoheptanedioate (meso-2,6-diaminopimelate, A2pm) combined with adjacent residues through its L-centre, as it is in Gram-negative and some Gram-positive organisms. The undecaprenol involved is ditrans,octacis-undecaprenol (for definitions, {iupac/misc/prenol#p6::click here}).
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CAS REGISTRY NUMBER
COMMENTARY
60976-26-3
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
malfunction
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point mutations in a MurG helical causes severe sporulation defects, but does not affect localization nor cause detectable defects during exponential growth. In strains in which the cardiolipin-synthesizing genes are deleted, MurG levels are diminished at the forespore, but MurG localization during sporulation is rescued by external addition of purified cardiolipin. During sporulation, lack of MurG localization heavily affects engulfment dynamics and sporulation efficiency, indicating a defect in MurG enzymatic activity linked to its diffuse localization
metabolism
physiological function
additional information
metabolism
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glycosyltransferase MurG catalyses the transfer of N-acetyl-D-glucosamine to lipid intermediate I on the bacterial peptidoglycan biosynthesis pathway
metabolism
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MurG is an essential N-acetylglucosaminyl transferase involved in catalyzing the final step of peptidoglycan subunit biosynthesis
physiological function
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MurG represents a temporary storage mechanism for excess protein that can later be remobilized into the active pool. Polar MurG can promote polar accumulation of anionic phospholipids
physiological function
MurG is an essential bacterial glycosyltransferase enzyme in Pseudomonas aeruginosa performing one of the key membrane steps of peptidoglycan synthesis catalyzing the transfer of N-acetyl glucosamine (GlcNAc) from its donor substrate, UDP-GlcNAc, to the acceptor substrate Lipid I
physiological function
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the glycosyltransferase MurG is necessary for cell wall synthesis at the spore during sporulation in the bacterium Bacillus subtilis. The enzyme localization is a critical factor in the regulation of proper enzyme function and catalysis
physiological function
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the biochemical production of lipid II requires four components, the lipid carrier undecaprenyl phosphate, UDP-MurNAc-pentapeptide, UDP-GlcNAc and the enzymes catalysing the formation of lipid II from these substrates, MraY and MurG
physiological function
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the biochemical production of lipid II requires four components, the lipid carrier undecaprenyl phosphate, UDP-MurNAc-pentapeptide, UDP-GlcNAc and the enzymes catalysing the formation of lipid II from these substrates, MraY and MurG
additional information
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docking of transition state analogues into MurG active site, overview
additional information
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MurG becomes polarly localized when expressed at high cellular concentrations, only at levels that saturate MurGs cellular requirement for growth, the polar MurG is not active and polar MurG is dynamic. It can be remobilized when MurG levels drop
additional information
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the active site residue Gln298 plays a critical role in ligand-target interactions, other active site residues like Arg168, Ser198, Arg202, Ser269, and His297 also play roles in binding interactions, docking study, and molecular modeling and structure validation, overview
additional information
large-scale conformational change in the relative orientations of the N- and C-terminal domains, which has the effect of widening the cofactor binding site and displacing the UDP-GlcNAc donor
additional information
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the active site residue Gln298 plays a critical role in ligand-target interactions, other active site residues like Arg168, Ser198, Arg202, Ser269, and His297 also play roles in binding interactions, docking study, and molecular modeling and structure validation, overview
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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
dUDP-N-acetyl-alpha-D-glucosamine + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
?
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?
UDP-N-acetylglucosamine + citronellyl-lipid I
UDP + N-acetylglucosamine-citronellyl-lipid I
UDP-N-acetylglucosamine + lipid I
UDP + lipid II
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i.e. Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
i.e. N-acetylglucosamine-(1-4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
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?
UDP-N-acetylglucosamine + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphospho-(6E,10E,14Z)-2,6,10,14-tetramethyl-hexadeca-2,6,10,14-tetraene
UDP + GlcNAcbeta(1-4)Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphospho-(6E,10E,14Z)-2,6,10,14-tetramethyl-hexadeca-2,6,10,14-tetraene
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?
UDP-N-acetylglucosamine + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphospho-(7S)-2,7-dimethyloct-2-ene
UDP + GlcNAcbeta(1-4)Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphospho-(7S)-2,7-dimethyloct-2-ene
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-
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?
UDP-N-acetylglucosamine + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphospho-p-nitrophenol
UDP + GlcNAcbeta(1-4)Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphospho-p-nitrophenol
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?
UDP-N-acetylglucosamine + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphobutane
UDP + GlcNAcbeta(1-4)Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphobutane
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-
-
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?
UDP-N-acetylglucosamine + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphododecane
UDP + GlcNAcbeta(1-4)Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphododecane
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-
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?
UDP-N-acetylglucosamine + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoicosane
UDP + GlcNAcbeta(1-4)Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoicosane
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?
UDP-N-acetylglucosamine + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphotetradecane
UDP + GlcNAcbeta(1-4)Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphotetradecane
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?
UDP-N-acetylglucosamine + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
UDP + GlcNAc-(1-4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
UDP-N-acetylglucosamine + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
UDP + GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
UDP-N-acetylglucosamine + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
UDP + N-acetylglucosamine-(1-4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
UDP-N-acetylglucosamine + MurNAc(Nepsilon-dansylpentapeptide)-pyrophosphoryl (R,S)-alpha-dihydrodecaprenol
UDP + N-acetylglucosamine-MurNAc(Nepsilon-dansylpentapeptide)-pyrophosphoryl (R,S)-alpha-dihydrodecaprenol
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very poor substrate
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?
UDP-N-acetylglucosamine + MurNAc(Nepsilon-dansylpentapeptide)-pyrophosphoryl (R,S)-alpha-dihydroheptaprenol
UDP + N-acetylglucosamine-MurNAc(Nepsilon-dansylpentapeptide)-pyrophosphoryl (R,S)-alpha-dihydroheptaprenol
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r
UDP-N-acetylglucosamine + MurNAc(Neta-dansylpentapeptide)-diphosphoryl (R,S-alpha-dihydroheptaprenol)
?
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UDP-N-acetylglucosamine + synthetic substrate analogue 2
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synthetic substrate analogue 2: a 10 carbon citronellyl derivative
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?
UDP-N-acetylglucosamine + synthetic substrate analogue 7
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synthetic substrate analogue 7: a derivative containing a 20 carbon chain with a cis-allylic double bond
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?
UDP-N-acetylglucosamine + citronellyl-lipid I
UDP + N-acetylglucosamine-citronellyl-lipid I
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undecaprenol replaced with a citronellol group
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?
UDP-N-acetylglucosamine + citronellyl-lipid I
UDP + N-acetylglucosamine-citronellyl-lipid I
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synthetic substrate, 55-carbon undecaprenol chain replaced by the 10-carbon chain of citronellol, biotin labeled substrate
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?
UDP-N-acetylglucosamine + citronellyl-lipid I
UDP + N-acetylglucosamine-citronellyl-lipid I
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synthetic substrate, 55-carbon undecaprenol chain replaced by the 10-carbon chain of citronellol, biotin labeled substrate
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?
UDP-N-acetylglucosamine + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
UDP + GlcNAc-(1-4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
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?
UDP-N-acetylglucosamine + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
UDP + GlcNAc-(1-4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
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?
UDP-N-acetylglucosamine + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
UDP + GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
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?
UDP-N-acetylglucosamine + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
UDP + GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
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lipid I
lipid II
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?
UDP-N-acetylglucosamine + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
UDP + GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
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lipid I
lipid II
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?
UDP-N-acetylglucosamine + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
UDP + N-acetylglucosamine-(1-4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
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?
UDP-N-acetylglucosamine + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
UDP + N-acetylglucosamine-(1-4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
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-
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?
UDP-N-acetylglucosamine + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
UDP + N-acetylglucosamine-(1-4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
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?
UDP-N-acetylglucosamine + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
UDP + N-acetylglucosamine-(1-4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
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?
additional information
?
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sMurG uses UDP-N-acetylglucosamine as substrate
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additional information
?
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sMurG uses UDP-N-acetylglucosamine as substrate
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additional information
?
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MurG binds significantly better to UDP than to CDP, ADP or GDP, E269 is an important residue in binding the nucleotide-sugar donor
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additional information
?
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MurG requires substrates containing an intact amide between the muramyl lactyl ether side-chain and the pentapeptide
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additional information
?
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no substrates: TDP-GlcNAc, C4 hydroxyl of UDP-GalNAc cannot form hydrogen bonds to A264 or N292
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additional information
?
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MurG prefers substrates that contain lipid chains that are considerably shorter than that of the natural substrate, compounds that contain a cis-allylic double bond react faster than compounds that do not
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additional information
?
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no substrates: P1-citronellyl-P2-alpha-D-glucosyl pyrophosphate, P1-citronellyl-P2-alpha-D-N-acetylglucoseaminyl pyrophosphate, P1-citronellyl-P2-alpha-D-N-acetylmuramyl pyrophosphate
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additional information
?
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role of enzyme in peptidoglycan biosynthesis pathway
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additional information
?
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UDP-N-acetylgalactosamine shows very little donor activity
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additional information
?
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UDP-GlcNAc is incorporated into lipid II using GlcNAc. MurG is also able to exchange the GlcNAc of the lipid II head group with GlcNAc of UDPGlcNAc, a simple exchange reaction
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additional information
?
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UDP-GlcNAc is incorporated into lipid II using GlcNAc. MurG is also able to exchange the GlcNAc of the lipid II head group with GlcNAc of UDPGlcNAc, a simple exchange reaction
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NATURAL SUBSTRATES
NATURAL PRODUCTS
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-acetylglucosamine + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
UDP + GlcNAc-(1-4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
UDP-N-acetylglucosamine + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
UDP + GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
UDP-N-acetylglucosamine + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
UDP + N-acetylglucosamine-(1-4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
additional information
?
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role of enzyme in peptidoglycan biosynthesis pathway
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UDP-N-acetylglucosamine + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
UDP + GlcNAc-(1-4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
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-
-
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?
UDP-N-acetylglucosamine + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
UDP + GlcNAc-(1-4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
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-
-
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?
UDP-N-acetylglucosamine + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
UDP + GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
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lipid I
lipid II
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?
UDP-N-acetylglucosamine + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
UDP + GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
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lipid I
lipid II
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?
UDP-N-acetylglucosamine + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
UDP + N-acetylglucosamine-(1-4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
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-
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?
UDP-N-acetylglucosamine + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
UDP + N-acetylglucosamine-(1-4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
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-
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?
UDP-N-acetylglucosamine + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
UDP + N-acetylglucosamine-(1-4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
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-
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?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(1R,3R,3aS,6aR)-1-{[2-({[(2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl] methyl}amino)-2-oxoethyl]carbamoyl}-3-(2-methoxyphenyl)-1-methyl-4,6-dioxo-5-phenyloctahydropyrrolo[3,4-c]pyrrol-2-ium
-
-
(1R,3S,3aR,6aS)-3-((S)-1,2-dihydroxyethyl)-N-(2-((((2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl)amino)-2-oxoethyl)-1-methyl-4,6-dioxo-5-phenyloctahydropyrrolo[3,4-c]pyrrole-1-carboxamide
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-
(1R,3S,3aR,6aS)-3-(2,3-dimethoxyphenyl)-N-[2-({[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl}amino)-2-oxoethyl]-1-methyl-4,6-dioxo-5-phenyloctahydropyrrolo[3,4-c]pyrrole-1-carboxamide
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-
(1R,3S,3aR,6aS)-N-[2-({[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl}amino)-2-oxoethyl]-1-methyl-4,6-dioxo-3,5-diphenyloctahydropyrrolo[3,4-c]pyrrole-1-carboxamide
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-
(1R,3S,3aR,6aS)-N-[2-({[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl}amino)-2-oxoethyl]-3-(2-methoxyphenyl)-1-methyl-4,6-dioxo-5-phenyloctahydropyrrolo[3,4-c]pyrrole-1-carboxamide
-
-
(1R,3S,3aR,6aS)-N-[2-({[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl}amino)-2-oxoethyl]-3-(2-methoxyphenyl)-2-methyl-4,6-dioxo-5-phenyloctahydropyrrolo[3,4-c]pyrrole-1-carboxamide
-
-
(2S)-N-{[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl}-1-{[(1R,3S,3aR,6aS)-3-(2-methoxyphenyl)-1-methyl-4,6-dioxo-5-phenyloctahydropyrrolo[3,4-c]pyrrol-1-yl]carbonyl}pyrrolidine-2-carboxamide
-
-
(2S)-N-{[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl}-1-{[(1R,3S,3aR,6aS)-5-ethyl-3-(2-methoxyphenyl)-1-methyl-4,6-dioxooctahydropyrrolo[3,4-c]pyrrol-1-yl]carbonyl}pyrrolidine-2-carboxamide
-
-
(4R,4aR,5aS,6R,12aS)-4-(dimethylamino)-1,5,10,12,12a-pentahydroxy-6-methyl-3,11-dioxo-3,4,4a,5,5a,6,11,12a- octahydrotetracene-2-carboxamide
-
-
({2-[3-(4-methoxybenzyl)-6-(methoxycarbonyl)-3,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridin-5-yl]-2-oxoethyl}sulfanyl)acetic acid
-
-
4-{[(1S,11aS)-5,11-dioxo-7-phenyl-2,3,5,10,11,11a-hexahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepin-1-yl]amino}-4-oxobutanoic acid
-
-
5'-({[(2R,3R,3aR,6aR)-3-carboxy-2-(2,3-dihydroxypropyl)-6a-methyl-4,6-dioxohexahydropyrrolo[3,4-b]pyrrol-5(1H)-yl]acetyl}amino)-5'-deoxyuridine
-
-
5'-({[(2S,3R,3aR,6aR)-3-carboxy-2-(2-methoxyphenyl)-6a-methyl-4,6-dioxohexahydropyrrolo[3,4-b]pyrrol-5(1H)-yl]acetyl}amino)-5'-deoxyuridine
-
-
5'-({[(2S,3R,3aS,6aR)-3-carboxy-2-(2,3-dimethoxyphenyl)-6a-methyl-4,6-dioxohexahydropyrrolo[3,4-b]pyrrol-5(1H)-yl]acetyl}amino)-5'-deoxyuridine
-
-
5'-({[(2S,3R,3aS,6aR)-3-carboxy-2-(2-methoxyphenyl)-6a-methyl-4,6-dioxohexahydropyrrolo[3,4-b]pyrrol-5(1H)-yl]acetyl}amino)-5'-deoxyuridine
-
-
5'-({[(2S,3R,3aS,6aR)-3-carboxy-2-(3,4-dimethoxyphenyl)-6a-methyl-4,6-dioxohexahydropyrrolo[3,4-b]pyrrol-5(1H)-yl]acetyl}amino)-5'-deoxyuridine
-
-
5'-({[(2S,3R,3aS,6aR)-3-carboxy-6a-methyl-4,6-dioxo-2-phenylhexahydropyrrolo[3,4-b]pyrrol-5(1H)-yl]acetyl}amino)-5'-deoxyuridine
-
-
5'-deoxy-5'-[(N-{[(2R,3R,4R,5R)-3-(methoxycarbonyl)-5-(2-methoxyphenyl)-2,4-dimethylpyrrolidinium-2-yl]carbonyl}glycyl) amino]uridine
-
-
5'-O-(3-{[(1R,3S,3aR,6aS)-3-(2-methoxyphenyl)-1-methyl-4,6-dioxo-5-phenyloctahydropyrrolo[3,4-c]pyrrol-1-yl]methoxy}-3-oxopropanoyl)uridine
-
-
5'-O-(4-{[(1R,3S,3aR,6aS)-3-(2-methoxyphenyl)-1-methyl-4,6-dioxo-5-phenyloctahydropyrrolo[3,4-c]pyrrol-1-yl]methoxy}-4-oxobutanoyl)uridine
-
-
5'-[(1-{[(2R,3R,4R,5S)-3,4-bis(methoxycarbonyl)-5-(2-methoxyphenyl)-2-methylpyrrolidin-2-yl]carbonyl}-L-prolyl)amino]-5'-deoxyuridine
-
-
5'-[(1-{[(2R,3S,4R,5S)-3,4-bis(methoxycarbonyl)-5-(2-methoxyphenyl)-2-methylpyrrolidin-2-yl]carbonyl}-L-prolyl)amino]-5'-deoxyuridine
-
-
5'-{[(3S,4R,5S)-3,4-bis(methoxycarbonyl)-5-(2-methoxyphenyl)-2-methyl-D-prolylglycyl]amino}-5'-deoxyuridine
-
-
5'-{[(3S5'-{[(3S,4R,5S)-3,4-bis(methoxycarbonyl)-2-methyl-5-phenyl-D-prolylglycyl]amino}-5'-deoxyuridine,4R,5S)-3,4-bis(methoxycarbonyl)-2-methyl-5-phenyl-D-prolylglycyl]amino}-5'-deoxyuridine
-
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murgocil
-
a highly bioactive staphylococcal-specific inhibitor of intracellular membrane-associated enzyme MurG
N-({6-[(4-cyano-2-fluorobenzyl)oxy]naphthalen-2-yl}sulfonyl)-D-glutamic acid
-
-
UDP
-
competitive inhibitor of UDP-GlcNAc donor, noncompetitive inhibitor of lipid I acceptor analogue
additional information
-
inhibitor binding mode, molecular modeling, overview
-
additional information
-
not inhibited by UMP, nor any other nucleotide diphosphate, UDP-N-acetylgalactosamine fails to show inhibitory activity even at millimolar concentrations
-
additional information
-
a transition state mimic is designed for MurG, containing a functionalised proline, linked through the alpha-carboxylic acid, via a spacer, to a uridine nucleoside. A set of 15 functionalised prolines are synthesised, using a convergent dipolar cycloaddition reaction, which are coupled via either a glycine, proline, sarcosine, or diester linkage to the 5'-position of uridine. The library of 18 final compounds are tested as inhibitors of Escherichia coli glycosyltransferase MurG, overview
-
additional information
-
beta-lactam potentiation screening to identify small molecules that augment the activity of beta-lactams against methicillin-resistant Staphylococcus aureus (MRSA), mechanistic characterization of a compound termed murgocil. Chemical synergy and cidality is achieved between murgocil and the beta-lactam imipenem mediated through MurG-dependent localization of penicillin-binding protein PBP2 to the division septum
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
cardiolipin
-
the activity of MurG is increased in the presence of cardiolipin
DMSO
-
high concentration (35%) of dimethylsulfoxide is necessary for maximal enzyme activity
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.053
Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphospho-(6E,10E,14Z)-2,6,10,14-tetramethyl-hexadeca-2,6,10,14-tetraene
-
pH 7.9, 37°C
0.047
Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphospho-(7S)-2,7-dimethyloct-2-ene
-
pH 7.9, 37°C
0.024
Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphospho-p-nitrophenol
-
pH 7.9, 37°C
0.022
Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphobutane
-
pH 7.9, 37°C
0.029
Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphododecane
-
pH 7.9, 37°C
0.052
Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoicosane
-
pH 7.9, 37°C
0.039
Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphotetradecane
-
pH 7.9, 37°C
0.02
Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
-
pH 7.9, 37°C
0.0028
MurNAc(Nepsilon-dansylpentapeptide)-pyrophosphoryl (R,S)-alpha-dihydroheptaprenol
-
-
-
0.0028 - 0.011
MurNAc(Neta-dansylpentapeptide)-diphosphoryl (R,S-alpha-dihydroheptaprenol)
additional information
additional information
-
continous fluorescence coupled enzyme assay method
-
0.0028
biotin-labelled lipid I analogue
-
in the presence of high concentration (35%) of dimethylsulfoxide
-
0.044
biotinylated citronellyl-lipid I
-
in the absence of additional metal ions
0.0028
MurNAc(Neta-dansylpentapeptide)-diphosphoryl (R,S-alpha-dihydroheptaprenol)
-
wild-type enzyme
0.0029
MurNAc(Neta-dansylpentapeptide)-diphosphoryl (R,S-alpha-dihydroheptaprenol)
-
mutant R260A
0.0042
MurNAc(Neta-dansylpentapeptide)-diphosphoryl (R,S-alpha-dihydroheptaprenol)
-
mutant N198A
0.0055
MurNAc(Neta-dansylpentapeptide)-diphosphoryl (R,S-alpha-dihydroheptaprenol)
-
mutant T15A
0.0059
MurNAc(Neta-dansylpentapeptide)-diphosphoryl (R,S-alpha-dihydroheptaprenol)
-
mutant Y105A
0.0071
MurNAc(Neta-dansylpentapeptide)-diphosphoryl (R,S-alpha-dihydroheptaprenol)
-
mutant S191A
0.0085
MurNAc(Neta-dansylpentapeptide)-diphosphoryl (R,S-alpha-dihydroheptaprenol)
-
mutant N291A
0.009
MurNAc(Neta-dansylpentapeptide)-diphosphoryl (R,S-alpha-dihydroheptaprenol)
-
mutant H124A
0.011
MurNAc(Neta-dansylpentapeptide)-diphosphoryl (R,S-alpha-dihydroheptaprenol)
-
mutant E125A
0.053
synthetic substrate analogue 7
-
derivative containing a 20 carbon chain with a cis-allylic double bond
-
0.15
UDP-N-acetylglucosamine
-
in the presence of high concentration (35%) of dimethylsulfoxide
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.933
MurNAc(Nepsilon-dansylpentapeptide)-pyrophosphoryl (R,S)-alpha-dihydroheptaprenol
-
-
-
0.123
biotinylated citronellyl-lipid I
-
in the absence of additional metal ions
14
synthetic substrate analogue 7
-
derivative containing a 20 carbon chain with a cis-allylic double bond
-
0.93
UDP-N-acetylglucosamine
-
in the presence of high concentration (35%) of dimethylsulfoxide
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
additional information
-
high-throughput method for measurement of enzyme activity based on addititon of UDP[3H]N-acetylglucosamine to membranes in which substrtae lipid I was preformed
additional information
-
enzyme activity is higher in vesicles containing cardiolipin than for vesicles with phosphatidylglycerol
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
7.5
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
25
35
37
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
-
during exponential growth, MurG localizes to septa of Bacillus subtilis, a zone of active peptidoglycan synthesis, and its N-terminal amphipathic helix is dispensable
additional information
-
MurG becomes polarly localized when expressed at high cellular concentrations, only at levels that saturate MurGs cellular requirement for growth, the polar MurG is not active
-
-
the enzyme localization to the membrane depends on the phospholipid cardiolipin
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PDB
SCOP
CATH
ORGANISM
UNIPROT
Pseudomonas aeruginosa (strain ATCC 15692 / DSM 22644 / CIP 104116 / JCM 14847 / LMG 12228 / 1C / PRS 101 / PAO1)
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
37800
38000
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SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
additional information
-
structure comparison with the enzyme from Escherichia coli, molecular modeling and structure validation, overview
additional information
-
structure comparison with the enzyme from Escherichia coli, molecular modeling and structure validation, overview
-
additional information
structure comparison with the MurG enzyme from Escherichia coli, overview
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Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
complex of MurG with UDP-GlcNAc, X-ray diffraction structure determination and analysis
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GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
native MurG is extracted from inner membrane vesicles of Escherichia coli cells, His-tagged MurG is purified by Ni-affinity chromatography using His-bind resin
-
recombinant His6-tagged enzyme from Escherichia coli strain C43 by nickel affinity chromatography
-
when overexpressed, enzyme copurifies with lipid vesicles deriving from intracellular vesicular mebranes
-
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli cells BL21-DE3-pLysS
-
gene murG, expression as His6-tagged enzyme in Escherichia coli strain C43
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gene murG, expression of C-terminal YFP-tagged enzyme in a murG-deficient strain of Bacillus subtilis
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into the vector pQE60 for expression of MurG in Escherichia coli JM109 cells
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MurG can be displayed in its active form on phage. Cloned from a pET-21a expression vector (Novagen) into the pFAB5cHis.TT.HUI phagemid vector as a fusion to the 3-end of a pelB leader sequence and the 5-end of a truncated gIII
-
the coding sequence is amplified from the Escherichia coli K12 chromosome and cloned for expression of His-tagged MurG in JM109 cells
-
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
F77E
-
site-directed mutagenesis, the mutant shows unaltered localization and cell growth comared to wild-type. Lipid II synthesis might be totally abrogated in mutant F77E explaining why the mutant is blocked in septation, cell wall synthesis is necessary for engulfment
S67E
-
site-directed mutagenesis, the mutant shows unaltered localization and cell growth comared to wild-type
V74E
-
site-directed mutagenesis, the mutant shows unaltered localization and cell growth comared to wild-type. Lipid II synthesis might be totally abrogated in mutant V74E explaining why the mutant is blocked in septation, cell wall synthesis is necessary for engulfment
V81E
-
site-directed mutagenesis, the mutant shows unaltered localization and cell growth comared to wild-type
E125A
-
amino acid substitution for evaluation of its role in the active site of MurG
E268A
H124A
-
amino acid substitution for evaluation of its role in the active site of MurG
H18A
-
amino acid substitution for evaluation of its role in the active site of MurG
L79E/F82E
-
site-directed mutagenesis, the mutant does not bind anionic phospholipids but can localize to the cell poles
N127A
-
amino acid substitution for evaluation of its role in the active site of MurG
N134A
-
amino acid substitution for evaluation of its role in the active site of MurG
N198A
-
amino acid substitution for evaluation of its role in the active site of MurG
N291A
-
amino acid substitution for evaluation of its role in the active site of MurG
Q288A
-
amino acid substitution for evaluation of its role in the active site of MurG
R260A
-
amino acid substitution for evaluation of its role in the active site of MurG
S191A
-
amino acid substitution for evaluation of its role in the active site of MurG
T15A
-
amino acid substitution for evaluation of its role in the active site of MurG
Y105A
-
amino acid substitution for evaluation of its role in the active site of MurG
additional information
-
none of the point mutations shows lethality and cells expressing MurG-GFP point mutants grow normally in absence of the wild-type murG allele
E268A
-
amino acid substitution for evaluation of its role in the active site of MurG
E268A
-
site-directed mutagenesis, in contrast to wild-type MurG, the MurG lipid interaction mutant often localizes to a single pole
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
biotechnology
drug development
synthesis
-
overexpression of enzyme results in formation of vesicular intracellular membranes enriched in cardiolipin. Cardiolipin content of cell is about 7fold increased
biotechnology
-
MurG is interesting to evaluate as a potential antibiotic target, as it has no counterpart in mammalian cells
biotechnology
-
MurG is interesting to evaluate as a potential antibiotic target, as it has no counterpart in mammalian cells
-
drug development
-
MurG is a target for drug development to treat diseases caused by Clostridium difficile, an etiologic agent of a variety of gastrointestinal diseases in humans including mild sporadic diarrhea and severe life-threatening pseudomembranous colitis
drug development
-
MurG is a target for drug development to treat diseases caused by Clostridium difficile, an etiologic agent of a variety of gastrointestinal diseases in humans including mild sporadic diarrhea and severe life-threatening pseudomembranous colitis
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