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(2E)-4-oxo-4-phenylbut-2-enoic acid
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(3E)-4-(4-methoxyphenyl)but-3-enoic acid
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(3E)-4-(4-methylphenyl)but-3-enoic acid
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(3E)-4-[3-(benzyloxy)-4-methoxyphenyl]but-3-enoic acid
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(3E)-4-[4-(benzyloxy)phenyl]but-3-enoic acid
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(acetyloxy)acetic acid
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(decanoylsulfanyl)acetic acid
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(dodecanoyloxy)acetic acid
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(E)-(4-dimethylamino)cinnamic acid
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(E)-3,4-methylenedioxycinnamic acid
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(E)-4-aminocinnamic acid
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(nicotinamidomethyl)phosphonic acid
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(R)-5-acetamido-4-oxo-6-phenyl-2-hexenoic acid
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reversible and irreversible inhibition
(S)-5-acetamido-4-oxo-6-phenyl-2-hexenoic acid
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reversible and irreversible inhibition
(S)-5-acetamido-7-methylthio-4-oxo-2-heptenoic acid
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reversible and irreversible inhibition
(S)-N-CBZ-4-amino-2-hydroxybutyric acid
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([(2S)-2-[(2-aminopropanoyl)amino]-3-phenylpropanoyl]oxy)acetic acid
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([N-[3-(1-leucylpyrrolidin-2-yl)-3-oxopropanoyl]-L-phenylalanyl]oxy)acetic acid
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([N-[3-(1-leucylpyrrolidin-2-yl)-3-oxopropanoyl]glycyl]oxy)acetic acid
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([[(2S)-1-(2-aminopropanoyl)pyrrolidin-2-yl]carbonyl]oxy)acetic acid
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([[(2S)-1-[[(2-aminopropanoyl)amino]acetyl]pyrrolidin-2-yl]carbonyl]oxy)acetic acid
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([[(4-amino-6-methyl-3-oxoheptanoyl)amino]acetyl]oxy)acetic acid
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2-trifluoromethylcinnamic acid
3,4-methylenedioxycinnamic acid
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3-(3-pyridyl)acrylic acid
3-benzoylpropionic acid
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4-phenyl-3-butenoic acid methyl ester
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at 0.01 mg/ml inhibition in vivo of proliferation of Ras-transformed WB rat liver epithelial cells, inhibitor leads to increased gap junction communication in the WB-Ras cells, overview
4-phenylbut-3-enoic acid
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PBA
5-(acetylamino)-4-oxo-6-phenyl-2-hexenoic acid
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5-(acetylamino)-4-oxo-6-phenyl-2-hexenoic acid methyl ester
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6-O-palmitoyl-L-ascorbate
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acetyl-D-Leu-OCH2COOH
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acetyl-D-Phe-OCH2COOH
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acetyl-DL-Phe-OCH2COOH
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acetyl-L-Leu-OCH2COOH
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acetyl-L-Phe-D-Phe-Gly
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acetyl-L-Phe-Gly
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only substrate for alpha-hydroxylation
acetyl-L-Phe-OCH2COOH
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adrenocorticotrophic hormone(1-10)
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alpha-N-acetyl-adrenocorticotrophic hormone(1-14)
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ascorbate
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above 0.4 mM for the purified enzyme, above 1.5 mM for the enzyme in crude extract
Cu2+
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at higher concentration
D-Tyr-Pro-Gly-Gly
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inhibition of activity with D-Tyr-Val-Gly
decanoyloxyacetic acid
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endorphin(51-61)NH2
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i.e. pro-adrenocorticotrophic hormone(1-10)
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endorphins
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and proendorphins
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ferrocyanide
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inhibiting above 0.6 mM
glutathione ethyl ester
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Glyoxylate 2-pyridylhydrazone
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Glyoxylate 4-carboxyphenylhydrazone
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Glyoxylate benzylhydrazone
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glyoxylate phenylhydrazone
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strongly
Glyoxylate phenylsemicarbazone
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Glyoxylate phenylthiosemicarbazone
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Glyoxylate semicarbazone
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glyoxylate thiosemicarbazone
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glyoxylate-N-hexyl-4-carbamoylphenylhydrazone
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strongly
Monoethyl fumarate
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mechanism-based inhibition
N,N-dimethyl-4-aminocinnamic acid
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N,S-dibenzoyl-L-cysteine
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N-(thiobenzoyl)-(D,L)-alanine
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N-acetyl-D-Leu-OCH2COOH
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competitive inhibitor
N-acetyl-L-Leu-OCH2COOH
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competitive inhibitor
N-acetyl-L-Phe-OCH2COOH
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competitive inhibitor
N-Carboxymethyl N'-phenylhydrazone
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weak inhibition
N-dansyl-4-aminocinnamate
a fluorescent molecule, an inactivator
N-dansyl-4-aminocinnamic acid
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N-phenylthiohydantoic acid
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O-(phenylcarbamoyl)glycolic acid
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O-acetyl-D-mandelyl-Gly
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O-benzamidoglycolic acid
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p-hydroxymercuribenzoate
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slightly
peptides
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especially those with COOH-terminal glycine residues
perdeuterated cinnamic acid
phenylpropynoic acid
i.e. phenylpropiolic acid
Pro-Leu-Gly hydroxamic acid
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S-(2-phenylthioacetyl)thioglycolic acid
S-(3-phenylthiopropionyl)thioglycolic acid
S-(4-methylthiobenzoyl)thioglycolic acid
S-(4-methylthiobenzoyl)thioglycolic acid ethyl ester
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S-(phenylthiocarbamoyl)-3-mercaptopropionic acid
S-(phenylthiocarbamoyl)thioglycolic acid
S-(thiobenzoyl)-(R,S)-thiolactic acid
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S-(thiobenzoyl)-4-mercapto-4-cyanopentanoic acid
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S-(thiobenzoyl)thioglycolic acid
S-(thiolauroyl)thioglycolic acid
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S-phenylmercaptoacetic acid
sulfite
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irreversible inactivation is Cu2+-dependent
trans-Benzoylacrylic acid
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mechanism-based inhibition
[(1R,2S)-2-phenylcyclopropyl]acetic acid
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[(4-Methoxybenzoyl)oxy]acetic acid
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[(phenylacetyl)oxy]acetic acid
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[(phenylacetyl)sulfanyl]acetic acid
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[[(2S)-2-(acetylamino)-3-phenylpropanoyl]oxy]acetic acid
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[[(2S)-2-(acetylamino)-3-phenylpropanoyl]sulfanyl]acetic acid
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[[(2S)-2-([[(2-aminopropanoyl)amino]acetyl]amino)-3-phenylpropanoyl]oxy]acetic acid
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[[(2S)-2-amino-3-phenylpropanoyl]oxy]acetic acid
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[[(2S)-pyrrolidin-2-ylcarbonyl]oxy]acetic acid
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[[(acetylamino)acetyl]oxy]acetic acid
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[[N-(4-amino-6-methyl-3-oxoheptanoyl)-L-phenylalanyl]oxy]acetic acid
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2-trifluoromethylcinnamic acid
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2-trifluoromethylcinnamic acid
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3-(3-pyridyl)acrylic acid
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3-(3-pyridyl)acrylic acid
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4-Phenyl-3-butenoic acid
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mechanism-based inhibition
4-Phenyl-3-butenoic acid
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irreversible turnover-dependent inhibition of the enzyme in vitro, at 0.1 mg/ml inhibition in vivo of proliferation of lung cancer cells and Ras-transformed WB rat liver epithelial cells, inhibitor leads to increased gap junction communication in the WB-Ras cells, overview
4-Phenyl-3-butenoic acid
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binds to the lumenal side of the enzyme where the peptidylglycine alpha-hydroxylating PHM activity is localized
4-Phenyl-3-butenoic acid
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4-Phenyl-3-butenoic acid
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Cinnamic acid
extensive dialysis of bifunctional PAM incubated with cinnamate yielded inactive enzyme unable to catalyze the production of glyoxylate from hippuric acid
D-Tyr-Val-Gly
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inhibition of activity with D-Tyr-Pro-Gly
D-Tyr-Val-Gly
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at 2 mM 82% inhibition, at 0.1 mM 45% inhibition
D-Tyr-Val-Gly
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inhibition above 20 mM of hydroxylation
diethyldithiocarbamate
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diethyldithiocarbamate
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copper chelator
diethyldithiocarbamate
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DDC
diethyldithiocarbamate
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copper chelator
EDTA
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EDTA
recombinant enzyme, alpha-hydroxylation activity can be restored by Mn2+, Zn2+, Cd2+, and Co2+, but not by Ca2+, Cu2+, Mg2+, and Fe3+
perdeuterated cinnamic acid
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perdeuterated cinnamic acid
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S-(2-phenylthioacetyl)thioglycolic acid
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S-(2-phenylthioacetyl)thioglycolic acid
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S-(2-phenylthioacetyl)thioglycolic acid
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S-(3-phenylthiopropionyl)thioglycolic acid
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S-(3-phenylthiopropionyl)thioglycolic acid
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S-(4-methylthiobenzoyl)thioglycolic acid
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S-(4-methylthiobenzoyl)thioglycolic acid
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S-(phenylthiocarbamoyl)-3-mercaptopropionic acid
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S-(phenylthiocarbamoyl)-3-mercaptopropionic acid
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S-(phenylthiocarbamoyl)thioglycolic acid
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S-(phenylthiocarbamoyl)thioglycolic acid
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S-(thiobenzoyl)thioglycolic acid
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S-(thiobenzoyl)thioglycolic acid
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S-phenylmercaptoacetic acid
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S-phenylmercaptoacetic acid
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Urocanic acid
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additional information
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activity is not affected by pepstatin A, phenylmethylsulfonyl fluoride, and soybean trypsin inhibitor
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additional information
peptide substrate amidation is strikingly sensitive to the exposure of cells to moderate hypoxia
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additional information
peptide substrate amidation is strikingly sensitive to the exposure of cells to moderate hypoxia
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additional information
cinnamic acid and cinnamic acid analogues are inhibitors or inactivators of PHM. The inactivation chemistry of the cinnamates exhibits all the attributes of a suicide-substrate. But no formation of an irreversible linkage between cinnamate and PHM in the inactivated enzyme is detected. Instead reversible formation of a Michael adduct between an active site nucleophile and cinnamate occurs that leads to inactive enzyme. Cinnamates are found in fruits, fruit juices, vegetables and flowers. Protection of PHM against the cinnamate-mediated inactivation by tiopronin. Molecular docking studies, overview
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additional information
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copper-deficiency decreases the enzyme activity
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additional information
peptide substrate amidation is strikingly sensitive to the exposure of cells to moderate hypoxia, hypoxia inhibits amidation of constitutively secreted POMC 18-kDa fragment
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additional information
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copper-deficiency decreases the enzyme activity
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additional information
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inhibition of peptidylglycine alpha-amidating monooxygenase by exploitation of factors affecting the stability and ease of formation of glycyl radicals, diverse glycine derivatives or substitutes, overview
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additional information
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form 1, AE-I, competitive inhibition by tripeptides with C-terminal glycine, most effective is methione within these peptides
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