BRENDA - Enzyme Database show
show all sequences of 1.14.17.3

Inactivation of peptidylglycine alpha-hydroxylating monooxygenase by cinnamic acid analogs

McIntyre, N.R.; Lowe, E.W.; Battistini, M.R.; Leahy, J.W.; Merkler, D.J.; J. Enzyme Inhib. Med. Chem. 31, 551-562 (2016)

Data extracted from this reference:

Inhibitors
Inhibitors
Commentary
Organism
Structure
(E)-(4-dimethylamino)cinnamic acid
-
Homo sapiens
(E)-3,4-methylenedioxycinnamic acid
-
Homo sapiens
(E)-4-aminocinnamic acid
-
Homo sapiens
2-trifluorocinnamic acid
-
Homo sapiens
2-trifluoromethylcinnamic acid
-
Rattus norvegicus
3,4-methylenedioxycinnamic acid
-
Rattus norvegicus
3-(3-pyridyl)acrylic acid
-
Homo sapiens
3-(3-pyridyl)acrylic acid
-
Rattus norvegicus
4-aminocinnamic acid
-
Rattus norvegicus
4-nitrocinnamic acid
-
Rattus norvegicus
Cinnamic acid
extensive dialysis of bifunctional PAM incubated with cinnamate yielded inactive enzyme unable to catalyze the production of glyoxylate from hippuric acid
Homo sapiens
Cinnamic acid
-
Rattus norvegicus
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
Homo sapiens
N,N-dimethyl-4-aminocinnamic acid
-
Rattus norvegicus
N-dansyl-4-aminocinnamate
a fluorescent molecule, an inactivator
Homo sapiens
N-dansyl-4-aminocinnamic acid
-
Rattus norvegicus
perdeuterated cinnamic acid
-
Homo sapiens
perdeuterated cinnamic acid
-
Rattus norvegicus
phenylpropionic acid
-
Rattus norvegicus
phenylpropynoic acid
i.e. phenylpropiolic acid
Homo sapiens
trans-cinnamic acid
-
Homo sapiens
Urocanic acid
-
Homo sapiens
Urocanic acid
-
Rattus norvegicus
Metals/Ions
Metals/Ions
Commentary
Organism
Structure
Cu2+
dependent on
Homo sapiens
Natural Substrates/ Products (Substrates)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
peptidylglycine + ascorbate + O2
Homo sapiens
-
peptidyl(2-hydroxyglycine) + dehydroascorbate + H2O
-
-
?
peptidylglycine + ascorbate + O2
Rattus norvegicus
the enzyme catalyzes the final reaction in the maturation of alpha-amidated peptide hormones
peptidyl(2-hydroxyglycine) + dehydroascorbate + H2O
-
-
?
Organism
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
Homo sapiens
P19021
-
-
Rattus norvegicus
P14925
-
-
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
acetyl-glycine + ascorbate + O2
-
745459
Rattus norvegicus
?
-
-
-
?
hippuric acid + ascorbate + O2
-
745459
Homo sapiens
glyoxylate + dehydroascorbate + H2O
-
-
-
?
peptidylglycine + ascorbate + O2
-
745459
Homo sapiens
peptidyl(2-hydroxyglycine) + dehydroascorbate + H2O
-
-
-
?
peptidylglycine + ascorbate + O2
-
745459
Rattus norvegicus
peptidyl(2-hydroxyglycine) + dehydroascorbate + H2O
-
-
-
?
peptidylglycine + ascorbate + O2
the enzyme catalyzes the final reaction in the maturation of alpha-amidated peptide hormones
745459
Rattus norvegicus
peptidyl(2-hydroxyglycine) + dehydroascorbate + H2O
-
-
-
?
Temperature Optimum [°C]
Temperature Optimum [°C]
Temperature Optimum Maximum [°C]
Commentary
Organism
37
-
assay at
Homo sapiens
pH Optimum
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
6
-
assay at
Homo sapiens
Cofactor
Cofactor
Commentary
Organism
Structure
ascorbate
-
Homo sapiens
Ki Value [mM]
Ki Value [mM]
Ki Value maximum [mM]
Inhibitor
Commentary
Organism
Structure
0.01
-
N-dansyl-4-aminocinnamic acid
37°C, pH 6.0
Rattus norvegicus
0.2
-
2-trifluoromethylcinnamic acid
37°C, pH 6.0
Rattus norvegicus
0.3
-
3,4-methylenedioxycinnamic acid
37°C, pH 6.0
Rattus norvegicus
0.5
-
4-aminocinnamic acid
37°C, pH 6.0
Rattus norvegicus
0.6
-
4-nitrocinnamic acid
37°C, pH 6.0
Rattus norvegicus
2
-
phenylpropionic acid
37°C, pH 6.0
Rattus norvegicus
3
-
N,N-dimethyl-4-aminocinnamic acid
37°C, pH 6.0
Rattus norvegicus
4
-
Cinnamic acid
37°C, pH 6.0
Rattus norvegicus
4
-
perdeuterated cinnamic acid
37°C, pH 6.0
Rattus norvegicus
6
-
3-(3-pyridyl)acrylic acid
37°C, pH 6.0
Rattus norvegicus
Cofactor (protein specific)
Cofactor
Commentary
Organism
Structure
ascorbate
-
Homo sapiens
Inhibitors (protein specific)
Inhibitors
Commentary
Organism
Structure
(E)-(4-dimethylamino)cinnamic acid
-
Homo sapiens
(E)-3,4-methylenedioxycinnamic acid
-
Homo sapiens
(E)-4-aminocinnamic acid
-
Homo sapiens
2-trifluorocinnamic acid
-
Homo sapiens
2-trifluoromethylcinnamic acid
-
Rattus norvegicus
3,4-methylenedioxycinnamic acid
-
Rattus norvegicus
3-(3-pyridyl)acrylic acid
-
Homo sapiens
3-(3-pyridyl)acrylic acid
-
Rattus norvegicus
4-aminocinnamic acid
-
Rattus norvegicus
4-nitrocinnamic acid
-
Rattus norvegicus
Cinnamic acid
extensive dialysis of bifunctional PAM incubated with cinnamate yielded inactive enzyme unable to catalyze the production of glyoxylate from hippuric acid
Homo sapiens
Cinnamic acid
-
Rattus norvegicus
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
Homo sapiens
N,N-dimethyl-4-aminocinnamic acid
-
Rattus norvegicus
N-dansyl-4-aminocinnamate
a fluorescent molecule, an inactivator
Homo sapiens
N-dansyl-4-aminocinnamic acid
-
Rattus norvegicus
perdeuterated cinnamic acid
-
Homo sapiens
perdeuterated cinnamic acid
-
Rattus norvegicus
phenylpropionic acid
-
Rattus norvegicus
phenylpropynoic acid
i.e. phenylpropiolic acid
Homo sapiens
trans-cinnamic acid
-
Homo sapiens
Urocanic acid
-
Homo sapiens
Urocanic acid
-
Rattus norvegicus
Ki Value [mM] (protein specific)
Ki Value [mM]
Ki Value maximum [mM]
Inhibitor
Commentary
Organism
Structure
0.01
-
N-dansyl-4-aminocinnamic acid
37°C, pH 6.0
Rattus norvegicus
0.2
-
2-trifluoromethylcinnamic acid
37°C, pH 6.0
Rattus norvegicus
0.3
-
3,4-methylenedioxycinnamic acid
37°C, pH 6.0
Rattus norvegicus
0.5
-
4-aminocinnamic acid
37°C, pH 6.0
Rattus norvegicus
0.6
-
4-nitrocinnamic acid
37°C, pH 6.0
Rattus norvegicus
2
-
phenylpropionic acid
37°C, pH 6.0
Rattus norvegicus
3
-
N,N-dimethyl-4-aminocinnamic acid
37°C, pH 6.0
Rattus norvegicus
4
-
Cinnamic acid
37°C, pH 6.0
Rattus norvegicus
4
-
perdeuterated cinnamic acid
37°C, pH 6.0
Rattus norvegicus
6
-
3-(3-pyridyl)acrylic acid
37°C, pH 6.0
Rattus norvegicus
Metals/Ions (protein specific)
Metals/Ions
Commentary
Organism
Structure
Cu2+
dependent on
Homo sapiens
Natural Substrates/ Products (Substrates) (protein specific)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
peptidylglycine + ascorbate + O2
Homo sapiens
-
peptidyl(2-hydroxyglycine) + dehydroascorbate + H2O
-
-
?
peptidylglycine + ascorbate + O2
Rattus norvegicus
the enzyme catalyzes the final reaction in the maturation of alpha-amidated peptide hormones
peptidyl(2-hydroxyglycine) + dehydroascorbate + H2O
-
-
?
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
acetyl-glycine + ascorbate + O2
-
745459
Rattus norvegicus
?
-
-
-
?
hippuric acid + ascorbate + O2
-
745459
Homo sapiens
glyoxylate + dehydroascorbate + H2O
-
-
-
?
peptidylglycine + ascorbate + O2
-
745459
Homo sapiens
peptidyl(2-hydroxyglycine) + dehydroascorbate + H2O
-
-
-
?
peptidylglycine + ascorbate + O2
-
745459
Rattus norvegicus
peptidyl(2-hydroxyglycine) + dehydroascorbate + H2O
-
-
-
?
peptidylglycine + ascorbate + O2
the enzyme catalyzes the final reaction in the maturation of alpha-amidated peptide hormones
745459
Rattus norvegicus
peptidyl(2-hydroxyglycine) + dehydroascorbate + H2O
-
-
-
?
Temperature Optimum [°C] (protein specific)
Temperature Optimum [°C]
Temperature Optimum Maximum [°C]
Commentary
Organism
37
-
assay at
Homo sapiens
pH Optimum (protein specific)
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
6
-
assay at
Homo sapiens
General Information
General Information
Commentary
Organism
metabolism
the enzyme catalyzes the final reaction in the maturation of alpha-amidated peptide hormones
Rattus norvegicus
physiological function
peptidylglycine alpha-amidating monooxygenase (PAM) is a bifunctional enzyme that catalyzes the final reaction in the maturation of alpha-amidated peptide hormones. Peptidylglycine alpha-hydroxylating monooxygenase (PHM) is the PAM domain responsible for the copper-, ascorbate- and O2-dependent hydroxylation of glycine-extended precursor peptides to the active alpha-amidated peptide and glyoxylate. Peptidylamidoglycolate lyase, EC 4.3.2.5, is the PAM domain responsible for the Zn(II)-dependent dealkylation of the alpha-hydroxyglycine-containing precursor to the final alpha-amidated peptide
Homo sapiens
General Information (protein specific)
General Information
Commentary
Organism
metabolism
the enzyme catalyzes the final reaction in the maturation of alpha-amidated peptide hormones
Rattus norvegicus
physiological function
peptidylglycine alpha-amidating monooxygenase (PAM) is a bifunctional enzyme that catalyzes the final reaction in the maturation of alpha-amidated peptide hormones. Peptidylglycine alpha-hydroxylating monooxygenase (PHM) is the PAM domain responsible for the copper-, ascorbate- and O2-dependent hydroxylation of glycine-extended precursor peptides to the active alpha-amidated peptide and glyoxylate. Peptidylamidoglycolate lyase, EC 4.3.2.5, is the PAM domain responsible for the Zn(II)-dependent dealkylation of the alpha-hydroxyglycine-containing precursor to the final alpha-amidated peptide
Homo sapiens
Other publictions for EC 1.14.17.3
No.
1st author
Pub Med
title
organims
journal
volume
pages
year
Activating Compound
Application
Cloned(Commentary)
Crystallization (Commentary)
Engineering
General Stability
Inhibitors
KM Value [mM]
Localization
Metals/Ions
Molecular Weight [Da]
Natural Substrates/ Products (Substrates)
Organic Solvent Stability
Organism
Oxidation Stability
Posttranslational Modification
Purification (Commentary)
Reaction
Renatured (Commentary)
Source Tissue
Specific Activity [micromol/min/mg]
Storage Stability
Substrates and Products (Substrate)
Subunits
Temperature Optimum [°C]
Temperature Range [°C]
Temperature Stability [°C]
Turnover Number [1/s]
pH Optimum
pH Range
pH Stability
Cofactor
Ki Value [mM]
pI Value
IC50 Value
Activating Compound (protein specific)
Application (protein specific)
Cloned(Commentary) (protein specific)
Cofactor (protein specific)
Crystallization (Commentary) (protein specific)
Engineering (protein specific)
General Stability (protein specific)
IC50 Value (protein specific)
Inhibitors (protein specific)
Ki Value [mM] (protein specific)
KM Value [mM] (protein specific)
Localization (protein specific)
Metals/Ions (protein specific)
Molecular Weight [Da] (protein specific)
Natural Substrates/ Products (Substrates) (protein specific)
Organic Solvent Stability (protein specific)
Oxidation Stability (protein specific)
Posttranslational Modification (protein specific)
Purification (Commentary) (protein specific)
Renatured (Commentary) (protein specific)
Source Tissue (protein specific)
Specific Activity [micromol/min/mg] (protein specific)
Storage Stability (protein specific)
Substrates and Products (Substrate) (protein specific)
Subunits (protein specific)
Temperature Optimum [°C] (protein specific)
Temperature Range [°C] (protein specific)
Temperature Stability [°C] (protein specific)
Turnover Number [1/s] (protein specific)
pH Optimum (protein specific)
pH Range (protein specific)
pH Stability (protein specific)
pI Value (protein specific)
Expression
General Information
General Information (protein specific)
Expression (protein specific)
KCat/KM [mM/s]
KCat/KM [mM/s] (protein specific)
745055
Yoo
The peptidylglycine-alpha-ami ...
Homo sapiens
Hum. Genomics
11
29
2017
-
-
1
-
1
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
2
2
-
-
-
744349
Chauhan
Stopped-flow studies of the r ...
Rattus norvegicus
Biochemistry
55
2008-2021
2016
-
-
1
-
6
-
-
1
-
1
-
1
-
1
-
-
1
1
-
-
-
-
2
-
1
-
-
-
1
-
-
1
-
-
-
-
-
1
1
-
6
-
-
-
-
1
-
1
-
1
-
-
-
1
-
-
-
-
2
-
1
-
-
-
1
-
-
-
-
-
-
-
-
-
744361
Kline
Substrate-induced carbon mono ...
Rattus norvegicus
Biochemistry
55
6652-6661
2016
1
-
1
-
7
-
-
-
-
1
-
1
-
1
-
-
1
1
-
-
-
-
1
-
-
-
-
-
-
-
-
1
-
-
-
1
-
1
1
-
7
-
-
-
-
-
-
1
-
1
-
-
-
1
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
1
1
-
-
-
745068
Martin-Diaconescu
Kbeta valence to core X-ray e ...
Rattus norvegicus
Inorg. Chem.
55
3431-3439
2016
-
-
-
-
2
-
-
-
-
1
-
-
-
1
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
2
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
745459
McIntyre
Inactivation of peptidylglyci ...
Homo sapiens, Rattus norvegicus
J. Enzyme Inhib. Med. Chem.
31
551-562
2016
-
-
-
-
-
-
23
-
-
1
-
2
-
2
-
-
-
-
-
-
-
-
5
-
1
-
-
-
1
-
-
1
10
-
-
-
-
-
1
-
-
-
-
23
10
-
-
1
-
2
-
-
-
-
-
-
-
-
5
-
1
-
-
-
1
-
-
-
-
2
2
-
-
-
746370
Zielinski
Expression of recombinant hum ...
Homo sapiens
Protein Expr. Purif.
119
102-109
2016
-
1
1
-
-
-
-
-
-
1
-
1
-
1
-
-
1
-
-
-
-
-
2
-
1
-
-
-
1
-
-
1
-
-
-
-
1
1
1
-
-
-
-
-
-
-
-
1
-
1
-
-
-
1
-
-
-
-
2
-
1
-
-
-
1
-
-
-
-
1
1
-
-
-
745327
Bonnemaison
Adaptor protein-1 complex aff ...
Homo sapiens, Rattus norvegicus
J. Biol. Chem.
290
21264-21279
2015
-
-
2
-
-
-
-
-
4
2
-
4
-
2
-
-
-
-
-
5
-
-
6
-
2
-
-
-
2
-
-
2
-
-
-
-
-
2
2
-
-
-
-
-
-
-
4
2
-
4
-
-
-
-
-
5
-
-
6
-
2
-
-
-
2
-
-
-
-
4
4
-
-
-
745332
Simpson
Striking oxygen sensitivity o ...
Drosophila melanogaster, Homo sapiens, Mus musculus
J. Biol. Chem.
290
24891-24901
2015
-
3
-
-
1
-
3
-
3
3
-
3
-
3
3
-
-
-
-
7
-
-
6
-
-
-
-
-
-
-
-
3
-
-
-
-
3
-
3
-
1
-
-
3
-
-
3
3
-
3
-
3
-
-
-
7
-
-
6
-
-
-
-
-
-
-
-
-
-
3
3
-
-
-
744315
Chauhan
Binding of copper and silver ...
Rattus norvegicus
Biochemistry
53
1069-1080
2014
-
-
-
-
5
-
-
-
-
2
-
-
-
1
-
-
-
-
-
-
-
-
1
-
1
-
-
-
1
-
-
1
-
-
-
-
-
-
1
-
5
-
-
-
-
-
-
2
-
-
-
-
-
-
-
-
-
-
1
-
1
-
-
-
1
-
-
-
-
1
1
-
-
-
745296
Vishwanatha
A histidine-rich linker regio ...
Mus musculus
J. Biol. Chem.
289
12404-12420
2014
-
-
1
-
1
-
-
-
3
-
-
-
-
1
-
-
1
-
-
2
-
-
-
1
-
-
-
-
1
1
-
-
-
-
-
-
-
1
-
-
1
-
-
-
-
-
3
-
-
-
-
-
-
1
-
2
-
-
-
1
-
-
-
-
1
1
-
-
-
3
3
-
-
-
745298
Abad
Reaction mechanism of the bic ...
Rattus norvegicus
J. Biol. Chem.
289
13726-13738
2014
-
-
-
-
-
-
-
-
-
1
-
5
-
1
-
-
-
1
-
-
-
-
5
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
1
-
5
-
-
-
-
-
-
-
-
5
-
-
-
-
-
-
-
-
-
-
2
2
-
-
-
727016
Kline
HHM motif at the CuH-site of p ...
Homo sapiens
Biochemistry
52
2586-2596
2013
-
-
1
-
3
-
-
4
-
1
-
1
-
1
-
-
-
-
-
-
-
-
3
-
-
-
-
4
1
-
-
1
-
-
-
-
-
1
1
-
3
-
-
-
-
4
-
1
-
1
-
-
-
-
-
-
-
-
3
-
-
-
-
4
1
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697630
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McIntyre
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Merkler
Substituted hippurates and hip ...
Blattella germanica, Homo sapiens, Rattus norvegicus
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699036
Trendel
Catalytically active peptidylg ...
Homo sapiens
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Bauer
Anti-inflammatory effects of 4 ...
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2007
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676976
Bauman
Large scale production of the ...
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687277
de la Lande
Long distance electron-transfe ...
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Bauman
pH Dependence of peptidylglyci ...
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Biochemistry
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672113
Evans
The catalytic role of the copp ...
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Biochemistry
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673155
Prohaska
Plasma peptidylglycine alpha-a ...
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Comp. Biochem. Physiol. B
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2006
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Crespo
The catalytic mechanism of pep ...
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Klinman
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The hydrogen peroxide reactivi ...
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676299
Driscoll
Murine atrial HL-1 cells expre ...
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Peptides
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Asada
Planarian peptidylglycine-hydr ...
Dugesia japonica
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Jaron
The catalytic role of the copp ...
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Jaron
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Francisco
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Structural and functional inve ...
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Identification, purification, ...
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Merkler
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Chikuma
Characterization of peptidylgl ...
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1
1
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1
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1
1
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1
1
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1
1
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3
1
1
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2
1
1
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-
-
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1
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1
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3
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438578
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1
4
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1
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4
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5
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The reaction product of peptid ...
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6
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1
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1
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1
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1
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6
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1
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1
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1
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1
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1
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1
1
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1
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2
1
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3
1
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438565
Gale
Peptidyl-glycine alpha-amidati ...
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5
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1
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6
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4
1
1
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1
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5
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4
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1
1
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4
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Purification of a peptidylglyc ...
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1988
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1
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2
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1
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1
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1
1
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1
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1
1
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3
2
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5
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2
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1
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11
2
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1
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5
1
1
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Murthy
Purification and characterizat ...
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3
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3
1
1
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2
1
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1
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1
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1
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1
1
1
3
1
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1
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1
3
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3
1
1
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2
1
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Mizuno
Peptide C-terminal alpha-amida ...
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1986
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2
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1
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3
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1
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1
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1
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2
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1
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1
1
1
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1
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1
1
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3
1
1
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Bendig
Post-translational processing ...
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2
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Sakata
Tissue distribution and charac ...
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6
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1
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6
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438575
Bradbury
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C-Terminal amide formation in ...
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Glembotski
Characterization of a peptide ...
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8
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1
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3
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8
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1
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Bradbury
Mechanism of C-terminal amide ...
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1
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