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dUDP-N-acetyl-alpha-D-glucosamine + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
?
-
-
-
?
UDP-N-acetyl-alpha-D-glucosamine + biotinylated citronellyl-lipid I
?
-
-
-
-
?
UDP-N-acetyl-alpha-D-glucosamine + C55-lipid I-Nepsilon-C6-dansyl thiourea
UDP + C55-lipid II-Nepsilon-C6-dansyl thiourea
UDP-N-acetylglucosamine + biotin-labelled lipid I analogue
?
-
-
-
-
?
UDP-N-acetylglucosamine + citronellyl-lipid I
UDP + N-acetylglucosamine-citronellyl-lipid I
UDP-N-acetylglucosamine + lipid I
UDP + lipid II
-
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
-
?
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
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
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
-
very poor substrate
-
?
UDP-N-acetylglucosamine + MurNAc(Nepsilon-dansylpentapeptide)-pyrophosphoryl (R,S)-alpha-dihydroheptaprenol
UDP + N-acetylglucosamine-MurNAc(Nepsilon-dansylpentapeptide)-pyrophosphoryl (R,S)-alpha-dihydroheptaprenol
-
-
-
r
UDP-N-acetylglucosamine + MurNAc(Neta-dansylpentapeptide)-diphosphoryl (R,S-alpha-dihydroheptaprenol)
?
-
-
-
?
UDP-N-acetylglucosamine + synthetic substrate analogue 2
?
-
synthetic substrate analogue 2: a 10 carbon citronellyl derivative
-
-
?
UDP-N-acetylglucosamine + synthetic substrate analogue 7
?
-
synthetic substrate analogue 7: a derivative containing a 20 carbon chain with a cis-allylic double bond
-
-
?
additional information
?
-
UDP-N-acetyl-alpha-D-glucosamine + C55-lipid I-Nepsilon-C6-dansyl thiourea

UDP + C55-lipid II-Nepsilon-C6-dansyl thiourea
-
-
-
?
UDP-N-acetyl-alpha-D-glucosamine + C55-lipid I-Nepsilon-C6-dansyl thiourea
UDP + C55-lipid II-Nepsilon-C6-dansyl thiourea
-
-
-
-
?
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
-
undecaprenol replaced with a citronellol group
-
?
UDP-N-acetylglucosamine + citronellyl-lipid I
UDP + N-acetylglucosamine-citronellyl-lipid I
-
synthetic substrate, 55-carbon undecaprenol chain replaced by the 10-carbon chain of citronellol, biotin labeled substrate
-
?
UDP-N-acetylglucosamine + citronellyl-lipid I
UDP + N-acetylglucosamine-citronellyl-lipid I
-
synthetic substrate, 55-carbon undecaprenol chain replaced by the 10-carbon chain of citronellol, biotin labeled substrate
-
?
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 + 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 + GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
-
lipid I
lipid II
-
?
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
-
?
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 + 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 + 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 + 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

?
-
-
sMurG uses UDP-N-acetylglucosamine as substrate
-
-
?
additional information
?
-
-
sMurG uses UDP-N-acetylglucosamine as substrate
-
-
?
additional information
?
-
-
-
-
-
?
additional information
?
-
-
MurG binds significantly better to UDP than to CDP, ADP or GDP, E269 is an important residue in binding the nucleotide-sugar donor
-
-
?
additional information
?
-
-
MurG requires substrates containing an intact amide between the muramyl lactyl ether side-chain and the pentapeptide
-
-
?
additional information
?
-
no substrates: TDP-GlcNAc, C4 hydroxyl of UDP-GalNAc cannot form hydrogen bonds to A264 or N292
-
-
?
additional information
?
-
-
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
-
-
?
additional information
?
-
-
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
-
-
?
additional information
?
-
-
role of enzyme in peptidoglycan biosynthesis pathway
-
-
?
additional information
?
-
-
UDP-N-acetylgalactosamine shows very little donor activity
-
-
?
additional information
?
-
-
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
-
-
?
additional information
?
-
-
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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(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
-
-
(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
-
-
(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
-
-
(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-(carboxyethynyl)-3,4-dihydroxybenzoic acid
-
-
2-(phosphonooxy)butanoic 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
-
-
cephalosporin C
-
50% inhibition at 0.014 mg/ml
Moenomycin
-
50% inhibition at 0.0106 mM
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
-
-
N-p-chlorobiphenyl-vancomycin
-
50% inhibition at 0.00125 mM
NG-p-chlorobiphenyl-vancomycin
-
50% inhibition at 0.0214 mM
nisin
-
50% inhibition at 0.016 mg/ml
[(5E)-5-[(3-bromo-5-chloro-2-hydroxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid
-
-
[1-hydroxy-2-(pyridin-3-yl)ethane-1,1-diyl]bis(phosphonic acid)
-
-
nikkomycin Z

-
Polyoxin D

-
ramoplanin

-
-
ramoplanin
-
90% inhibition at 0.02 mM
ramoplanin A2

-
ristocetin A

strong antimycobacterial MurG inhibitor
ristocetin A
-
strong antimycobacterial MurG inhibitor
tunicamycin

-
-
tunicamycin
-
50% inhibition at 0.0003 mg/ml
UDP

-
competitive inhibitor of UDP-GlcNAc donor, noncompetitive inhibitor of lipid I acceptor analogue
Vancomycin

-
50% inhibition at 0.009 mg/ml
Vancomycin
-
50% inhibition at 0.0157 mM
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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1.5
2'-dUDP-N-acetyl-alpha-D-glucosamine
-
0.0028 - 0.037
biotin-labelled lipid I analogue
-
0.036 - 0.044
biotinylated citronellyl-lipid I
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)
0.553
synthetic substrate analogue 2
-
10 carbon citronellyl derivative
-
0.053
synthetic substrate analogue 7
-
0.045 - 0.15
UDP-N-acetylglucosamine
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
-
0.037
biotin-labelled lipid I analogue
-
in the presence of MgCl2
-
0.036
biotinylated citronellyl-lipid I

-
in the presence of Mn2+
0.037
biotinylated citronellyl-lipid I
-
in the presence of Mg2+
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

-
-
0.053
synthetic substrate analogue 7
-
derivative containing a 20 carbon chain with a cis-allylic double bond
-
0.0098
UDP-GlcNAc

mutant N291A
0.012
UDP-GlcNAc
mutant E125A
0.027
UDP-GlcNAc
wild-type enzyme
0.033
UDP-GlcNAc
mutant R260A
0.038
UDP-GlcNAc
mutant T15A
0.047
UDP-GlcNAc
mutant H124A
0.05
UDP-GlcNAc
mutant Y105A
0.056
UDP-GlcNAc
mutant N198A
1.03
UDP-GlcNAc
mutant S191A
0.045
UDP-N-acetylglucosamine

-
in the absence of additional metal ions
0.046
UDP-N-acetylglucosamine
-
in the presence of Mn2+
0.058
UDP-N-acetylglucosamine
-
in the presence of Mg2+
0.058
UDP-N-acetylglucosamine
-
in the presence of MgCl2
0.15
UDP-N-acetylglucosamine
-
-
0.15
UDP-N-acetylglucosamine
-
in the presence of high concentration (35%) of dimethylsulfoxide
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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
0.0087 - 0.0095
nikkomycin Z
0.0508 - 0.055
Polyoxin D
0.0035
PyDT-1
Mycolicibacterium smegmatis
-
pH 8.0, 37°C
0.0224 - 0.0235
ramoplanin A2
0.00096 - 0.0014
ristocetin A
0.002
ToXa-1
Mycolicibacterium smegmatis
-
pH 8.0, 37°C
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
0.0087
nikkomycin Z

Hydrogenivirga sp. 128-5-R1-1
pH 8.0, 37°C
0.0095
nikkomycin Z
Mycolicibacterium smegmatis
-
pH 8.0, 37°C
0.0508
Polyoxin D

Hydrogenivirga sp. 128-5-R1-1
pH 8.0, 37°C
0.055
Polyoxin D
Mycolicibacterium smegmatis
-
pH 8.0, 37°C
0.0224
ramoplanin A2

Hydrogenivirga sp. 128-5-R1-1
pH 8.0, 37°C
0.0235
ramoplanin A2
Mycolicibacterium smegmatis
-
pH 8.0, 37°C
0.00096
ristocetin A

Hydrogenivirga sp. 128-5-R1-1
pH 8.0, 37°C
0.0014
ristocetin A
Mycolicibacterium smegmatis
-
pH 8.0, 37°C
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