Information on EC 6.1.1.20 - phenylalanine-tRNA ligase

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The expected taxonomic range for this enzyme is: Archaea, Bacteria, Eukaryota

EC NUMBER
COMMENTARY hide
6.1.1.20
-
RECOMMENDED NAME
GeneOntology No.
phenylalanine-tRNA ligase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
ATP + L-phenylalanine + tRNAPhe = AMP + diphosphate + L-phenylalanyl-tRNAPhe
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Aminoacylation
esterification
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Aminoacyl-tRNA biosynthesis
-
-
phenylalanine metabolism
-
-
tRNA charging
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-
SYSTEMATIC NAME
IUBMB Comments
L-phenylalanine:tRNAPhe ligase (AMP-forming)
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CAS REGISTRY NUMBER
COMMENTARY hide
9055-66-7
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Q9Y9I6: alpha-subunit, Q9Y9I3: beta-subunit
Q9Y9I6 and Q9Y9I3
SwissProt
Manually annotated by BRENDA team
Aeropyrum pernix DSM 11879
Q9Y9I6: alpha-subunit, Q9Y9I3: beta-subunit
Q9Y9I6 and Q9Y9I3
SwissProt
Manually annotated by BRENDA team
mutant strain UA22 carrying both wild-type and mutant alleles of gene pheS due to polyploidy
UniProt
Manually annotated by BRENDA team
wild-type strain 168, overproduced in Escherichia coli JM109
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-
Manually annotated by BRENDA team
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-
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Manually annotated by BRENDA team
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-
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Manually annotated by BRENDA team
gene pheS
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
2 activities
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-
Manually annotated by BRENDA team
strain K
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-
Manually annotated by BRENDA team
strain K-10
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-
Manually annotated by BRENDA team
strain MRE-600
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Manually annotated by BRENDA team
strain NP37 carrying the thermosensitive point mutation A294G in the active site
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-
Manually annotated by BRENDA team
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-
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Manually annotated by BRENDA team
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-
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Manually annotated by BRENDA team
strain Spain 7
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Manually annotated by BRENDA team
i.e. Lactobacillus amylovorus, several strains, e.g. strains 16698T and AD5, from Finnish porcine isolates, housekeeping gene pheS encoding the alpha-subunit
-
-
Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
Methanobacterium thermoautotrophicus
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-
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Manually annotated by BRENDA team
strain 489
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-
Manually annotated by BRENDA team
strain 489
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-
Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
strain 133
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-
Manually annotated by BRENDA team
strain G9A
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-
Manually annotated by BRENDA team
KOD1, class II enzyme
Q76KA8 and Q76KA8
UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
C9QTZ3
architecture of four helix-bundle interface, characteristic of class IIc heterotetrameric aaRSs, is changed, each of the two long helices belonging to CLM transformed into the coil-short helix structural fragments. The N-terminal domain of the alpha-subunit in EcPheRS forms compact triple helix domain
malfunction
-
mutation of the human mitochondrial phenylalanine-tRNA synthetase causes infantile-onset epilepsy and cytochrome c oxidase deficiency
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
2'-deoxyadenosine 5'-triphosphate + L-phenylalanine + tRNAPhe
2'-deoxyadenosine 5'-monophosphate + diphosphate + L-phenylalanyl-tRNAPhe
show the reaction diagram
2-chloroadenosine 5'-triphosphate + phenylalanine + tRNAPhe
2-chloroadenosine 5'-monophosphate + diphosphate + phenylalanyl-tRNAPhe
show the reaction diagram
3'-deoxyadenosine 5'-triphosphate + L-phenylalanine + tRNAPhe
3'-deoxyadenosine 5'-monophosphate + diphosphate + L-phenylalanyl-tRNAPhe
show the reaction diagram
ATP + 3,4-dihydroxy-L-phenylalanine + tRNAPhe
AMP + diphosphate + 3,4-dihydroxy-L-phenylalanyl-tRNAPhe
show the reaction diagram
ATP + 4-acetyl-L-phenylalanine + tRNAPhe
AMP + diphosphate + 4-acetyl-L-phenylalanyl-tRNAPhe
show the reaction diagram
-
recombinant mutant T251G, no activity with A294G
-
?
ATP + 4-azido-L-phenylalanine + tRNAPhe
AMP + diphosphate + 4-azido-L-phenylalanyl-tRNAPhe
show the reaction diagram
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recombinant mutant A294G
-
?
ATP + 4-bromo-L-phenylalanine + tRNAPhe
AMP + diphosphate + 4-bromo-L-phenylalanyl-tRNAPhe
show the reaction diagram
-
recombinant mutant A294G
-
?
ATP + 4-cyano-L-phenylalanine + tRNAPhe
AMP + diphosphate + 4-cyano-L-phenylalanyl-tRNAPhe
show the reaction diagram
-
recombinant mutant A294G
-
?
ATP + 4-ethynyl-L-phenylalanine + tRNAPhe
AMP + diphosphate + 4-ethynyl-L-phenylalanyl-tRNAPhe
show the reaction diagram
-
recombinant mutant A294G
-
?
ATP + 4-iodo-L-phenylalanine + amber tRNAPheCUA
AMP + diphosphate + 4-iodo-L-phenylalanyl-amber tRNAPheCUA
show the reaction diagram
ATP + 4-iodo-L-phenylalanine + tRNAPhe
AMP + diphosphate + 4-iodo-L-phenylalanyl-tRNAPhe
show the reaction diagram
-
recombinant mutant A294G
-
?
ATP + benzofuranylalanine + tRNAPhe
AMP + diphosphate + L-benzofuranylalanyl-tRNAPhe
show the reaction diagram
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benzofuranylalanine is a substrate for aminoacylation of tRNAPhe by mutant enzyme with mutation A294G in the alpha-subunit
-
-
?
ATP + DL-m-tyrosine + tRNAPhe
AMP + diphosphate + DL-m-tyrosyl-tRNAPhe
show the reaction diagram
ATP + L-Phe + tRNAPhe
AMP + diphosphate + L-phenylalanyl-tRNAPhe
show the reaction diagram
ATP + L-phenylalanine + (s-pA)tRNAPhe
AMP + diphosphate + L-phenylalanyl-(s-pA)tRNAPhe
show the reaction diagram
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-
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-
?
ATP + L-phenylalanine + (s-pC)tRNAPhe
AMP + diphosphate + L-phenylalanyl-(s-pC)tRNAPhe
show the reaction diagram
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-
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?
ATP + L-phenylalanine + (s-pG)tRNAPhe
AMP + diphosphate + L-phenylalanyl-(s-pG)tRNAPhe
show the reaction diagram
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?
ATP + L-phenylalanine + (s-pU)tRNAPhe
AMP + diphosphate + L-phenylalanyl-(s-pU)tRNAPhe
show the reaction diagram
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-
-
-
?
ATP + L-phenylalanine + tRNAPhe
AMP + diphosphate + bis-L-phenylalanyl-tRNAPhe
show the reaction diagram
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mechanism, formation of bisphenylalanyl-tRNAPhe with tRNA substrates from Thermus thermophilus, isoacceptor I, and from Escherichia coli, yeast and human, the second phenylalanyl residue is attached to tRNA approximately 50 times more slowly than the first one, the presence of modofoed nucleotides is not necessary for tRNAPhe overcharging
overcharged product cannot be isolated from living cells
ir
ATP + L-phenylalanine + tRNAPhe
AMP + diphosphate + L-phenylalanyl-tRNAPhe
show the reaction diagram
ATP + L-phenylalanine + tRNAPhe-s6 G76
AMP + diphosphate + L-phenylalanyl-tRNAPhe-s6 G76
show the reaction diagram
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tRNAPhe variant, 370fold reduced activity compared to wild-type tRNAPhe
-
?
ATP + L-Tyr + tRNAPhe
AMP + diphosphate + L-tyrosyl-tRNAPhe
show the reaction diagram
-
cytosolic PheRS contains an editing site, which upon disruption abolishes both cis and trans editing of Tyr-tRNAPhe. Wild-type mitochondrial PheRS lacks cis and trans editing and can synthesisze Tyr-tRNAPhe
-
-
?
ATP + L-tyrosine + tRNAPhe
AMP + diphosphate + L-tyrosinyl-tRNAPhe
show the reaction diagram
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PheRS misactivates Tyr but is able to correct the mistake using a proofreading editing activity, overview, after evading editing by PheRS, Tyr-tRNAPhe is recognized by elongation factor Tu EF-Tu, involved in translational quality control including substrate selection by aminoacyl-tRNA synthetases, as efficiently as the cognate Phe-tRNAPhe, overview
-
-
?
ATP + L-tyrosine + tRNAPhe
AMP + diphosphate + L-tyrosyl-tRNAPhe
show the reaction diagram
GTP + L-phenylalanine + tRNAPhe
GMP + diphosphate + L-phenylalanyl-tRNAPhe
show the reaction diagram
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40fold lower activity compared to ATP
-
?
N6-methyladenosine 5'-triphosphate + L-phenylalanine + tRNAPhe
N6-methyladenosine 5'-monophosphate + diphosphate + L-phenylalanyl-tRNAPhe
show the reaction diagram
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additional information
?
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
ATP + L-phenylalanine + tRNAPhe
AMP + diphosphate + L-phenylalanyl-tRNAPhe
show the reaction diagram
ATP + L-tyrosine + tRNAPhe
AMP + diphosphate + L-tyrosinyl-tRNAPhe
show the reaction diagram
-
PheRS misactivates Tyr but is able to correct the mistake using a proofreading editing activity, overview, after evading editing by PheRS, Tyr-tRNAPhe is recognized by elongation factor Tu EF-Tu, involved in translational quality control including substrate selection by aminoacyl-tRNA synthetases, as efficiently as the cognate Phe-tRNAPhe, overview
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-
?
additional information
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
GTP
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40fold lower activity than with ATP
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Cd2+
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can substitute for Zn2+ in diadenosine 5',5'''-P1,P4-tetraphosphate synthesis
Iron
regulatory function in mutant strain UA22
KCl
-
optimal concentration is 10 mM
Mn2+
-
not bound to the active site, located at the interface of alpha and beta subunits
spermine
optimal at 1 mM, stimulates 2-4fold the second reaction step, the ester bond formation between the 2'-hydroxyl group of the 3'-terminal adenosine base of the tRNA and the carboxylic acid function of phenylalanine
additional information
-
enzyme metal binding site structure, overview
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(2R,3R,3aS,5aR,10R,10aR)-N-(3,4-dichlorophenyl)-10-hydroxy-4-oxo-2-phenyl-2,3,3a,4,5a,10-hexahydrofuro[2,3-c]indeno[1,2-b]furan-3-carboxamide
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-
(2R,3R,3aS,5aR,10S,10aR)-N-(3,4-dichlorophenyl)-10-hydroxy-4-oxo-2-phenyl-2,3,3a,4,5a,10-hexahydrofuro[2,3-c]indeno[1,2-b]furan-3-carboxamide
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(2R,3R,3aS,5aS,10aR)-N-(3,4-dichlorophenyl)-4,10-dioxo-2-phenyl-2,3,3a,4,5a,10-hexahydrofuro[2,3-c]indeno[1,2-b]furan-3-carboxamide
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IC50: 0.0026 mM; IC50: 0.0031 mM
(2R,3R,3aS,5aS,10R,10aS)-N-(3,4-dichlorophenyl)-10-hydroxy-4-oxo-2-phenyl-2,3,3a,4,5a,10-hexahydrofuro[2,3-c]indeno[1,2-b]furan-3-carboxamide
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IC50: 0.00047 mM; IC50: 0.00051 mM
(2R,3R,3aS,5aS,10S,10aS)-N-(3,4-dichlorophenyl)-10-hydroxy-4-oxo-2-phenyl-2,3,3a,4,5a,10-hexahydrofuro[2,3-c]indeno[1,2-b]furan-3-carboxamide
-
IC50: 0.00017 mM; IC50: 0.00026 mM
(2Z)-2-(cyclopropylimino)-3-(2-thienylmethyl)-1,3-thiazolidin-4-one
(2Z)-2-[(3-chlorophenyl)imino]-3-(2-thienylmethyl)-1,3-thiazolidin-4-one
(3a'R,6a'S)-5'-(3,4-dichlorophenyl)-3'-phenyl-3a',6a'-dihydro-2'H-spiro[indene-2,1'-pyrrolo[3,4-c]pyrrole]-1,3,4',6'(3'H,5'H)-tetrone
(3a'R,6a'S)-5'-(3-chloro-4-methylphenyl)-3'-phenyl-3a',6a'-dihydro-2'H-spiro[indene-2,1'-pyrrolo[3,4-c]pyrrole]-1,3,4',6'(3'H,5'H)-tetrone
(3a'S,6a'R)-5'-(3,4-dichlorophenyl)-3'-phenyl-3a',6a'-dihydro-2'H-spiro[indene-2,1'-pyrrolo[3,4-c]pyrrole]-1,3,4',6'(3'H,5'H)-tetrone
(3a'S,6a'R)-5'-(3-chloro-4-methylphenyl)-3'-phenyl-3a',6a'-dihydro-2'H-spiro[indene-2,1'-pyrrolo[3,4-c]pyrrole]-1,3,4',6'(3'H,5'H)-tetrone
(3aR,6aS)-5-(3,4-dichlorophenyl)-3-phenyl-3a,6a-dihydrospiro[furo[3,4-c]pyrrole-1,2'-indene]-1',3',4,6(3H,5H)-tetrone
(3aR,6aS)-5-(3-chloro-4-methylphenyl)-3-phenyl-3a,6a-dihydrospiro[furo[3,4-c]pyrrole-1,2'-indene]-1',3',4,6(3H,5H)-tetrone
(3aS,6aR)-5-(3,4-dichlorophenyl)-3-phenyl-3a,6a-dihydrospiro[furo[3,4-c]pyrrole-1,2'-indene]-1',3',4,6(3H,5H)-tetrone
(3aS,6aR)-5-(3-chloro-4-methylphenyl)-3-phenyl-3a,6a-dihydrospiro[furo[3,4-c]pyrrole-1,2'-indene]-1',3',4,6(3H,5H)-tetrone
(3aS,6aR)-5-[4-chloro-3-(trifluoromethyl)phenyl]-3-phenyl-3a,6a-dihydrospiro[furo[3,4-c]pyrrole-1,2'-indene]-1',3',4,6(3H,5H)-tetrone
(3R,3aR,6aS)-5-(3,4-dichlorophenyl)-3-phenyl-3a,6a-dihydrospiro[furo[3,4-c]pyrrole-1,2'-indene]-1',3',4,6(3H,5H)-tetrone
(3R,4S,5R)-4-[(3,4-dichlorophenyl)carbamoyl]-1',3'-dioxo-5-phenyl-1',3',4,5-tetrahydro-3H-spiro[furan-2,2'-indene]-3-carboxylic acid
-
IC50: 0.011 mM; IC50: 0.033 mM
(3S,3aR,6aS)-5-(3,4-dichlorophenyl)-3-phenyl-3a,6a-dihydrospiro[furo[3,4-c]pyrrole-1,2'-indene]-1',3',4,6(3H,5H)-tetrone
(4-[4-[(3-chlorobenzyl)oxy]-3-methylbenzoyl]piperazin-1-yl)(tetrahydrofuran-2-yl)methanone
(4-[4-[2-(3-chlorophenyl)-2-hydroxyethyl]-3-methylbenzoyl]piperazin-1-yl)(tetrahydrofuran-2-yl)methanone
(5-[3-chloro-4-[(3-chlorobenzyl)oxy]phenyl]-1,3,4-oxadiazol-2-yl)acetic acid
1-(3-bromophenyl)-2-[(2-methoxybenzyl)amino]ethanol
-
IC50: 110 nM
1-(3-chlorophenyl)-2-[(2-phenoxybenzyl)amino]ethanol
-
IC50: 31 nM
1-(3-iodophenyl)-2-[(2-phenoxybenzyl)amino]ethanol
-
IC50: 32 nM
1-(3-methoxyphenyl)-2-[(2-phenoxybenzyl)amino]ethanol
-
IC50: 83 nM
1-(3-[[4-(3,5-dichlorophenyl)piperazin-1-yl]sulfonyl]phenyl)-3-(1,3-thiazol-2-yl)urea
1-(4-bromothiophen-2-yl)-2-[(2-methoxybenzyl)amino]ethanol
-
IC50: 50 nM
1-(4-bromothiophen-2-yl)-2-[(2-phenoxybenzyl)amino]ethanol
-
IC50: 120 nM
1-(4-bromothiophen-2-yl)-2-[(2-[[4-(methylsulfonyl)benzyl]oxy]benzyl)amino]ethanol
-
IC50: 26 nM
1-(4-bromothiophen-2-yl)-2-[[2-(2-hydroxyethoxy)benzyl]amino]ethanol
-
IC50: 8 nM
1-(4-bromothiophen-2-yl)-2-[[2-(but-3-en-1-yloxy)benzyl]amino]ethanol
-
IC50: 18 nM
1-(4-bromothiophen-2-yl)-2-[[2-(methoxymethoxy)benzyl]amino]ethanol
-
IC50: 35 nM
1-(4-bromothiophen-2-yl)-2-[[2-(pyridin-2-ylmethoxy)benzyl]amino]ethanol
-
IC50: 43 nM
1-(4-bromothiophen-2-yl)-2-[[2-(pyridin-3-ylmethoxy)benzyl]amino]ethanol
-
IC50: 18 nM
1-(4-bromothiophen-2-yl)-2-[[2-(pyridin-4-ylmethoxy)benzyl]amino]ethanol
-
IC50: 16 nM
1-[3-(hydroxymethyl)phenyl]-2-[(2-phenoxybenzyl)amino]ethanol
-
IC50: 570 nM
1-[3-[(4-pyridin-2-ylpiperazin-1-yl)sulfonyl]phenyl]-3-(1,3-thiazol-2-yl)urea
-
binding structure and inhibition mechanism, the inhibitor molecule binds with ring A deep inside the enzyme, and ring B in the place that is occupied by the aromatic ring of phenylalanine, overview
1-[4-[(3-chlorobenzyl)oxy]-3-methylbenzoyl]piperidine-4-carboxamide
1-[4-[2-(3-chlorophenyl)ethyl]-3-methylbenzoyl]piperidine-4-carboxamide
1-[[2-(3-chlorophenyl)-1-methyl-4-oxo-1,4-dihydroquinazolin-6-yl]carbonyl]piperidine-4-carboxamide
2',3'-Ribodeoxy-ATP
2-(5-[3-chloro-4-[(3-chlorobenzyl)oxy]phenyl]-1,3,4-oxadiazol-2-yl)acetamide
2-(5-[3-chloro-4-[(3-chlorobenzyl)oxy]phenyl]-1,3,4-oxadiazol-2-yl)ethanol
2-chloro-N-(3-chlorophenyl)-4-[(4-methyl-3-oxopiperazin-1-yl)carbonyl]benzenesulfonamide
2-phenylacetamidine
-
competitive with respect to phenylalanine
2-[(2-methoxybenzyl)amino]-1-(3-methylphenyl)ethanol
-
IC50: 110 nM
2-[(2-methoxybenzyl)amino]-1-[3-(trifluoromethoxy)phenyl]ethanol
-
IC50: 190 nM
2-[(2-methoxybenzyl)amino]-1-[3-(trifluoromethyl)phenyl]ethanol
-
IC50: 160 nM
2-[(2-methylbenzyl)amino]-1-[3-(trifluoromethyl)phenyl]ethanol
-
IC50: 790 nM
2-[([2-hydroxy-2-[3-(trifluoromethyl)phenyl]ethyl]amino)methyl]benzoic acid
-
IC50: 2500 nM
2-[([2-hydroxy-2-[3-(trifluoromethyl)phenyl]ethyl]amino)methyl]phenol
-
IC50: 100 nM
2-[2-([[2-(4-bromothiophen-2-yl)-2-hydroxyethyl]amino]methyl)phenoxy]-N-(3-hydroxypropyl)acetamide
-
IC50: 110 nM
2-[2-([[2-(4-bromothiophen-2-yl)-2-hydroxyethyl]amino]methyl)phenoxy]-N-ethylacetamide
-
IC50: 32 nM
2-[2-([[2-(4-bromothiophen-2-yl)-2-hydroxyethyl]amino]methyl)phenoxy]acetamide
-
IC50: 42 nM
2-[3-chloro-4-[(3-chlorobenzyl)oxy]phenyl]-1,3,4-oxadiazole
2-[3-chloro-4-[(3-chlorobenzyl)oxy]phenyl]-5-(methylsulfanyl)-1,3,4-oxadiazole
2-[3-chloro-4-[(3-chlorobenzyl)oxy]phenyl]-5-(methylsulfinyl)-1,3,4-oxadiazole
2-[3-chloro-4-[(3-chlorobenzyl)oxy]phenyl]-5-(methylsulfonyl)-1,3,4-oxadiazole
2-[3-chloro-4-[(3-chlorobenzyl)oxy]phenyl]-5-ethyl-1,3,4-oxadiazole
2-[3-chloro-4-[(3-chlorobenzyl)oxy]phenyl]-5-methyl-1,3,4-oxadiazole
2-[4-[2-([[2-(4-bromothiophen-2-yl)-2-hydroxyethyl]amino]methyl)phenoxy]butyl]-1H-isoindole-1,3(2H)-dione
-
IC50: 22 nM
2-[[2-(1H-benzimidazol-2-ylmethoxy)benzyl]amino]-1-(4-bromothiophen-2-yl)ethanol
-
IC50: 26 nM
2-[[2-(2-aminoethoxy)benzyl]amino]-1-(4-bromothiophen-2-yl)ethanol
-
IC50: 220 nM
2-[[2-(4-aminobutoxy)benzyl]amino]-1-(4-bromothiophen-2-yl)ethanol
-
IC50: 22 nM
2-[[2-(benzyloxy)benzyl]amino]-1-(4-bromothiophen-2-yl)ethanol
-
IC50: 10 nM
2-[[2-(benzyloxy)benzyl]amino]-1-[3-(trifluoromethyl)phenyl]ethanol
-
IC50: 50 nM
2-[[2-(difluoromethoxy)benzyl]amino]-1-[3-(trifluoromethyl)phenyl]ethanol
-
IC50: 260 nM
2-[[2-(prop-2-en-1-yloxy)benzyl]amino]-1-[3-(trifluoromethyl)phenyl]ethanol
-
IC50: 58 nM
3'-Deoxyadenosine 5'-triphosphate
3'-Methoxy-ATP
-
-
3'-Methyladenosine 5'-triphosphate
3-chloro-4-[(3-chlorobenzyl)oxy]-N-(1-hydroxypropan-2-yl)benzamide
3-chloro-4-[(3-chlorobenzyl)oxy]-N-(4-hydroxybutyl)benzamide
3-chloro-4-[(3-chlorobenzyl)oxy]-N-(cyclopropylmethyl)benzamide
3-chloro-4-[(3-chlorobenzyl)oxy]-N-[2-(ethylamino)ethyl]-N-methylbenzenesulfonamide
3-chloro-4-[(3-chlorobenzyl)oxy]-N-[2-(morpholin-4-yl)ethyl]benzamide
3-chloro-N-[2-methyl-4-[(4-methyl-3-oxopiperazin-1-yl)carbonyl]phenyl]benzenesulfonamide
3-[2-([[2-(4-bromothiophen-2-yl)-2-hydroxyethyl]amino]methyl)phenoxy]-N-(3-hydroxypropyl)propanamide
-
IC50: 25 nM
3-[2-([[2-(4-bromothiophen-2-yl)-2-hydroxyethyl]amino]methyl)phenoxy]-N-[2-(methylamino)-2-oxoethyl]propanamide
-
IC50: 36 nM
3-[2-([[2-(4-bromothiophen-2-yl)-2-hydroxyethyl]amino]methyl)phenoxy]propanoic acid
-
IC50: 58 nM
4-(3-chloro-4-[[(3-chlorophenyl)sulfinyl]methyl]benzoyl)-1-methylpiperazin-2-one
4-(3-chloro-4-[[(3-chlorophenyl)sulfonyl]methyl]benzoyl)-1-methylpiperazin-2-one
4-chloro-5-[(3-chlorobenzyl)oxy]-2-(1,3,4-oxadiazol-2-yl)pyridine
4-chloro-5-[(3-chlorobenzyl)oxy]-N-(1-ethyl-1H-pyrazol-5-yl)pyridine-2-carboxamide
4-chloro-5-[(3-chlorobenzyl)oxy]-N-(1-hydroxypropan-2-yl)pyridine-2-carboxamide
4-chloro-5-[(3-chlorobenzyl)oxy]-N-(4-hydroxybutyl)pyridine-2-carboxamide
4-chloro-5-[(3-chlorobenzyl)oxy]-N-(4-hydroxycyclohexyl)pyridine-2-carboxamide
4-chloro-5-[(3-chlorobenzyl)oxy]-N-(cyclopropylmethyl)pyridine-2-carboxamide
4-chloro-5-[(3-chlorobenzyl)oxy]-N-[2-(morpholin-4-yl)ethyl]pyridine-2-carboxamide
4-[2-([[2-(4-bromothiophen-2-yl)-2-hydroxyethyl]amino]methyl)phenoxy]-N-(3-hydroxypropyl)butanamide
-
IC50: 26 nM
4-[2-([[2-(4-bromothiophen-2-yl)-2-hydroxyethyl]amino]methyl)phenoxy]-N-[2-(methylamino)-2-oxoethyl]butanamide
-
IC50: 30 nM
4-[2-([[2-(4-bromothiophen-2-yl)-2-hydroxyethyl]amino]methyl)phenoxy]butanoic acid
-
IC50: 43 nM
4-[3-chloro-4-[(3-chlorobenzyl)oxy]benzoyl]-1-methylpiperazin-2-one
5-[3-chloro-4-[(3-chlorobenzyl)oxy]phenyl]-1,3,4-oxadiazol-2-amine
5-[3-chloro-4-[(3-chlorobenzyl)oxy]phenyl]-1,3,4-oxadiazole-2-carboxamide
5-[4-chloro-5-[(3-chlorobenzyl)oxy]pyridin-2-yl]-1,3,4-oxadiazol-2-amine
5-[4-chloro-5-[(3-chlorobenzyl)oxy]pyridin-2-yl]-1,3,4-oxadiazole-2-carboxamide
Alkylamides of phenylalanine
-
the inhibitor constant decreases with increasing length of the alkyl chain
benzylguanidine
-
competitive with respect to phenylalanine
Chloramphenicol
CTP
-
-
diphosphate
-
-
DL-m-tyrosine
-
;
DTT
-
-
E. coli tRNAPhe
-
inhibition by formation of a tight complex of the enzyme with the diphosphate formed during the aminoacylation
-
GTP
-
-
L-phenylalanyl-5'-adenylate
-
-
L-phenylalanyl-adenylate
-
-
L-tyrosine
-
-
L-tyrosyl-adenylate
-
-
Methicillin
methyl 3-chloro-4-[(3,4-difluorobenzyl)oxy]benzoate
methyl 3-chloro-4-[(3-chlorobenzyl)oxy]benzoate
methyl 3-chloro-4-[(3-fluorobenzyl)oxy]benzoate
methyl 4-[(1R,2R)-2-(3-chlorophenyl)-1,2-dihydroxyethyl]-3-methylbenzoate
methyl 4-[(1S,2S)-2-(3-chlorophenyl)-1,2-dihydroxyethyl]-3-methylbenzoate
methyl 4-[(3-chlorobenzoyl)amino]-3-methylbenzoate
methyl 4-[(3-chlorobenzyl)(methyl)amino]-3-methylbenzoate
methyl 4-[(3-chlorobenzyl)amino]-3-methylbenzoate
methyl 4-[(3-chlorobenzyl)oxy]-3-methylbenzoate
methyl 4-[(3-chlorobenzyl)oxy]benzoate
methyl 4-[(3-chlorophenyl)carbamoyl]benzoate
methyl 4-[(E)-2-(3-chlorophenyl)ethenyl]-3-methylbenzoate
methyl 4-[[(3-chlorophenyl)(methyl)amino]methyl]benzoate
methyl 4-[[(3-chlorophenyl)amino]methyl]benzoate
muciproin
N-(1-[3-chloro-4-[(4-chlorobenzyl)oxy]benzyl]pyrrolidin-3-yl)acetamide
N-(5-[3-chloro-4-[(3-chlorobenzyl)oxy]phenyl]-1,3,4-oxadiazol-2-yl)acetamide
N-benzyl-D-amphetamine
-
most potent competitive inhibitor, selectivity for bacterial enzyme
N-benzylbenzamidine
-
competitive with respect to phenylalanine
N-[2-(1H-indol-3-yl)ethyl]-3-[(1,3-thiazol-2-ylcarbamoyl)amino]benzenesulfonamide
N2-[[2-([[2-(4-bromothiophen-2-yl)-2-hydroxyethyl]amino]methyl)phenoxy]acetyl]-N-methylglycinamide
-
IC50: 120 nM
N6-Benzyladenosine 5'-triphosphate
ochratoxin A
-
-
Ochratoxine
-
-
Ochrotoxine A
-
cometitive
phenyl-thiazolylurea-sulfonamides
phenyl-thiazolylurea-sulfonamido-aminoethyl-chloroindol
phenyl-thiazolylurea-sulfonamido-aminoethyl-chloroindole
-
-
phenyl-thiazolylurea-sulfonamido-aminoethylindol
phenyl-thiazolylurea-sulfonamido-aminoethylindole
-
strong inhibition, competitive to L-phenylalanine, cytotoxic effects on CHO cells and bacteria
PheOH-AMP
tRNAPhe Cp75
-
tRNAPhe with cytosine phosphate residue at position 75
-
tRNAPhe s4-U75
-
tRNAPhe with 4-thiouridine residue at position 75
-
tRNAPhe s4-U76
-
tRNAPhe with 4-thiouridine residue at position 76
-
tRNAPhe s4-U77
-
tRNAPhe with 4-thiouridine residue at position 77
-
tRNAPhe s4-Up77
-
tRNAPhe with 4-thiouridine phosphate residue at position 77
-
[2-([[2-(4-bromothiophen-2-yl)-2-hydroxyethyl]amino]methyl)phenoxy]acetonitrile
-
IC50: 49 nM
[3-chloro-4-[(3-chlorobenzyl)oxy]phenyl](4-methylpiperazin-1-yl)methanone
[3-chloro-4-[(3-chlorophenoxy)methyl]phenyl](4-methylpiperazin-1-yl)methanone
[4-([3-chloro-4-[(3-chlorobenzyl)oxy]phenyl]sulfonyl)piperazin-1-yl](4-methylphenyl)methanone
[4-[1-(3-chlorophenyl)-2-hydroxyethyl]-3-methylphenyl](4-methylpiperazin-1-yl)methanone
additional information
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
DTT
-
activates
elongation factor 1alpha
-
interaction enhances the activity
-
additional information
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00016
(s-pA)tRNAPhe
-
-
-
0.00017
(s-pG)tRNAPhe
-
-
-
0.085 - 0.4
2'-deoxyadenosine 5'-triphosphate
0.05 - 0.2
2-Chloroadenosine 5'-triphosphate
1.54
2-deoxyadenosine 5'-triphosphate
-
aminoacylation
0.3
3'-deoxadenosine 5'-triphosphate
-
cytoplasmic
0.82 - 1
3'-Deoxyadenosine 5'-triphosphate
0.38 - 0.65
3,4-dihydroxy-L-phenylalanine
0.0058 - 2.5
ATP
923
benzofuranylalanine
-
-
0.012 - 0.13
DL-m-tyrosine
0.0018 - 0.05
L-Phe
0.00048 - 0.233
L-phenylalanine
0.86
L-Tyr
-
pH 7.2, 37C, cytosolic enzyme
0.32 - 3
L-tyrosine
0.81
N6-methyladenosine 5'-triphosphate
-
aminoacylation
0.00045 - 0.083
Phe
0.000066 - 0.018
tRNAPhe
additional information
additional information