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Information on EC 2.4.1.227 - undecaprenyldiphospho-muramoylpentapeptide beta-N-acetylglucosaminyltransferase
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2.4.1.227 undecaprenyldiphospho-muramoylpentapeptide beta-N-acetylglucosaminyltransferaseIUBMB Comments
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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The expected taxonomic range for this enzyme is: Bacteria, Eukaryota, Archaea
Reaction Schemes
Synonyms
translocase ii, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
acetylglucosaminyltransferase, uridine diphosphoacetylglucosamine-acetylmuramoylpentapeptide pyrophospholipid
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gene murG enzyme
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gene murG proteins
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Lipid I acetylglucosaminyltransferase
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MsmegMurG
MurG
MurG glycosyltransferase
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MurG transferase
peptidoglycan glycosyltransferase
proteins, gene murG
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UDP-acetylglucosamine-acetylmuramoylpentapeptide pyrophospholipid acetylglucosaminyltransferase
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MurG
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MurG
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MurG transferase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
UDP-N-acetyl-alpha-D-glucosamine + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol = UDP + beta-D-GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
UDP-N-acetyl-alpha-D-glucosamine + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol = UDP + beta-D-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-acetyl-alpha-D-glucosamine + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol = UDP + beta-D-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 SOURCE
PATHWAYS
BRENDA
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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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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-acetyl-alpha-D-glucosamine + biotinylated citronellyl-lipid I
?
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?
UDP-N-acetyl-alpha-D-glucosamine + C55-lipid I-Nepsilon-C6-dansyl thiourea
UDP + C55-lipid II-Nepsilon-C6-dansyl thiourea
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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?
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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?
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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?
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-acetyl-alpha-D-glucosamine + C55-lipid I-Nepsilon-C6-dansyl thiourea
UDP + C55-lipid II-Nepsilon-C6-dansyl thiourea
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?
UDP-N-acetyl-alpha-D-glucosamine + C55-lipid I-Nepsilon-C6-dansyl thiourea
UDP + C55-lipid II-Nepsilon-C6-dansyl thiourea
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?
UDP-N-acetyl-alpha-D-glucosamine + C55-lipid I-Nepsilon-C6-dansyl thiourea
UDP + C55-lipid II-Nepsilon-C6-dansyl thiourea
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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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?
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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?
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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?
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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-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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?
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
-
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
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
INHIBITOR
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
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-
(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
-
-
(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
-
-
(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
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(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
-
-
(5E)-5-[(4-tert-butylphenyl)methylidene]-3-[(4-methylpiperidin-1-yl)methyl]-2-sulfanylidene-1,3-thiazolidin-4-one
-
-
(5E)-5-[(5-bromofuran-2-yl)methylidene]-1-(4-chlorophenyl)-1,3-diazinane-2,4,6-trione
-
-
({2-[3-(4-methoxybenzyl)-6-(methoxycarbonyl)-3,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridin-5-yl]-2-oxoethyl}sulfanyl)acetic acid
-
-
2-[(5Z)-5-(1-benzyl-5-bromo-2-oxo-1,2-dihydro-3H-indol-3-ylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]ethane-1-sulfonic acid
-
-
3-[[(3E)-3-[[5-(4-bromophenyl)furan-2-yl]methylidene]-2-oxo-5-phenyl-2,3-dihydro-1H-pyrrol-1-yl]methyl]benzoic 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
-
-
5-(3-[(E)-[1-(3-chlorophenyl)-2,4,6-trioxo-1,3-diazinan-5-ylidene]methyl]-2,5-dimethyl-1H-pyrrol-1-yl)benzene-1,3-dicarboxylic acid
-
-
5-([3-[2-(4-tert-butylphenoxy)ethoxy]phenyl]methylidene)-2-sulfanylidene-1,3-diazinane-4,6-dione
-
-
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
-
-
[(5E)-5-[(3-bromo-5-chloro-2-hydroxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic 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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DISEASE
TITLE OF PUBLICATION
LINK TO PUBMED
Whooping Cough
The MurG glycosyltransferase provides an oligomeric scaffold for the cytoplasmic steps of peptidoglycan biosynthesis in the human pathogen Bordetella pertussis.
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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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IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0014
(5E)-5-[(4-tert-butylphenyl)methylidene]-3-[(4-methylpiperidin-1-yl)methyl]-2-sulfanylidene-1,3-thiazolidin-4-one
Escherichia coli
-
pH 7.9, temperature not specified in the publication
0.0064
(5E)-5-[(5-bromofuran-2-yl)methylidene]-1-(4-chlorophenyl)-1,3-diazinane-2,4,6-trione
Escherichia coli
-
pH 7.9, temperature not specified in the publication
0.0035
2-[(5Z)-5-(1-benzyl-5-bromo-2-oxo-1,2-dihydro-3H-indol-3-ylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]ethane-1-sulfonic acid
Escherichia coli
-
pH 7.9, temperature not specified in the publication
0.0054
3-[[(3E)-3-[[5-(4-bromophenyl)furan-2-yl]methylidene]-2-oxo-5-phenyl-2,3-dihydro-1H-pyrrol-1-yl]methyl]benzoic acid
Escherichia coli
-
pH 7.9, temperature not specified in the publication
0.0014
5-(3-[(E)-[1-(3-chlorophenyl)-2,4,6-trioxo-1,3-diazinan-5-ylidene]methyl]-2,5-dimethyl-1H-pyrrol-1-yl)benzene-1,3-dicarboxylic acid
Escherichia coli
-
pH 7.9, temperature not specified in the publication
0.004
5-([3-[2-(4-tert-butylphenoxy)ethoxy]phenyl]methylidene)-2-sulfanylidene-1,3-diazinane-4,6-dione
Escherichia coli
-
pH 7.9, temperature not specified in the publication
0.0034
[(5E)-5-[(3-bromo-5-chloro-2-hydroxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid
Escherichia coli
-
pH 7.9, temperature not specified in the publication
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
0.0000141