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release of a C-terminal amino acid, but little or no action with -Asp, -Glu, -Arg, -Lys or -Pro
release of a C-terminal amino acid, but little or no action with -Asp, -Glu, -Arg, -Lys or -Pro
mechanism
-
36317, 36319, 36322, 36341, 36344, 36345, 36346, 36349, 36352, 36353, 36356, 36361
release of a C-terminal amino acid, but little or no action with -Asp, -Glu, -Arg, -Lys or -Pro
relationships between structure and mechanism, zinc environment and substrate complexes
-
release of a C-terminal amino acid, but little or no action with -Asp, -Glu, -Arg, -Lys or -Pro
mechanisms elucidated from complex with inactivator 2-benzyl-3-iodo-propanoic acid
-
release of a C-terminal amino acid, but little or no action with -Asp, -Glu, -Arg, -Lys or -Pro
pK values of active site residues, analysis of kinetics and mechanism under alkaline conditions
-
release of a C-terminal amino acid, but little or no action with -Asp, -Glu, -Arg, -Lys or -Pro
molecular dynamics characterization of active cavity
-
release of a C-terminal amino acid, but little or no action with -Asp, -Glu, -Arg, -Lys or -Pro
conceptual model of relationship between activity, mechanism and conformational mobility
-
release of a C-terminal amino acid, but little or no action with -Asp, -Glu, -Arg, -Lys or -Pro
rapid release: Tyr, Phe, Trp, Leu, Ile, Thr, Gln, His, Ala, Val, homoserine, slow release: Asn, Ser, Lys, MetSO2, very slow release: Gly, Asp, Glu, CySO3H, S-carboxymethylcysteine, not released: Pro, Hyp, Arg
-
release of a C-terminal amino acid, but little or no action with -Asp, -Glu, -Arg, -Lys or -Pro
evidence of general base pathway
-
release of a C-terminal amino acid, but little or no action with -Asp, -Glu, -Arg, -Lys or -Pro
relationships between structure and mechanism, different catalytic sites for esters and peptides, role of mechanic strain discussed
-
release of a C-terminal amino acid, but little or no action with -Asp, -Glu, -Arg, -Lys or -Pro
correlations between mechanism, kinetics, and structure, intermediates and rate-determining steps
-
release of a C-terminal amino acid, but little or no action with -Asp, -Glu, -Arg, -Lys or -Pro
evidence for acyl-enzyme intermediates
-
release of a C-terminal amino acid, but little or no action with -Asp, -Glu, -Arg, -Lys or -Pro
relationships between enzyme structure and catalytic properties, catalytic groups, intermediates, and conformational changes during catalysis conform to "induced fit hypothesis"
-
-
-
release of a C-terminal amino acid, but little or no action with -Asp, -Glu, -Arg, -Lys or -Pro
cryospectrokinetic characterization of intermediates, time-course of reaction
-
release of a C-terminal amino acid, but little or no action with -Asp, -Glu, -Arg, -Lys or -Pro
promoted water pathway, mechanistic model
-
release of a C-terminal amino acid, but little or no action with -Asp, -Glu, -Arg, -Lys or -Pro
catalytic mechanism involving the Zn2+ ion and residue Glu270 with ester or protein substrates, the tetrahydrate transition state is stabilized by Arg127, overview
-
release of a C-terminal amino acid, but little or no action with -Asp, -Glu, -Arg, -Lys or -Pro
residues Glu270 and Arg127 are important for activity, the catalytic triad consists of Ile275, Tyr248, and Ala250, residues at positions 202, 254, and 268 are important for substrate specificity
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(Ala)4 + H2O
(Ala)3 + L-Ala
-
-
-
ir
(S)-hippuryl-alpha-MePhe + H2O
?
-
-
-
?
(S)-hippuryl-alpha-methylphenyllactic acid + H2O
?
-
-
-
?
(S)-hippuryl-OPhe + H2O
?
-
-
-
?
3-(2-furyl)acryloyl-L-Phe-L-Ala + H2O
3-(2-furyl)acryloyl-L-Phe + L-Ala
-
-
-
-
?
3-(2-furyl)acryloyl-L-Phe-L-Ile + H2O
3-(2-furyl)acryloyl-L-Phe + L-Ile
-
-
-
-
?
3-(2-furyl)acryloyl-L-Phe-L-Leu + H2O
3-(2-furyl)acryloyl-L-Phe + L-Leu
-
-
-
-
?
3-(2-furyl)acryloyl-L-Phe-L-Met + H2O
3-(2-furyl)acryloyl-L-Phe + L-Met
-
-
-
-
?
3-(2-furyl)acryloyl-L-Phe-L-Phe + H2O
3-(2-furyl)acryloyl-L-Phe + L-Phe
-
-
-
-
?
3-(2-furyl)acryloyl-L-Phe-L-Trp + H2O
3-(2-furyl)acryloyl-L-Phe + L-Trp
-
-
-
-
?
3-(2-furyl)acryloyl-L-Phe-L-Val + H2O
3-(2-furyl)acryloyl-L-Phe + L-Val
-
-
-
-
?
4-chlorocinnamoyl-L-beta-phenyllactate + H2O
4-chlorocinnamic acid + L-beta-phenyllactate
-
-
-
-
?
5-dimethyl-aminonaphthalene-1-sulfonyl-Ala-Ala-L-beta-phenyllactate + H2O
5-dimethyl-aminonaphthalene-1-sulfonyl-Ala-Ala + L-beta-phenyllactate
-
-
-
ir
5-dimethyl-aminonaphthalene-1-sulfonyl-Ala-Ala-Phe + H2O
5-dimethyl-aminonaphthalene-1-sulfonyl-Ala-Ala + L-Phe
-
-
-
ir
Ac-Phe-ThiaPhe + H2O
Phe + ThiaPhe
-
-
-
-
?
angiotensin I + H2O
angiotensin II + His-Leu
angiotensin I + H2O
Asp-Arg-Val-Tyr-Ile-His-Pro-Phe-His + Leu
-
-
-
ir
angiotensin I + H2O
des-Leu10 angiotensin I + Leu
anisylazoformyl-L-Phe + H2O
anisylazoformic acid + L-Phe
-
-
-
?
apolipoprotein B + H2O
?
-
-
-
-
?
benzoyl-Gly-Gly-L-alpha-hydroxy-beta-phenyllactate + H2O
benzoyl-Gly-Gly-L-alpha-hydroxy-beta-phenyllactate + ?
-
-
-
ir
benzoyl-Gly-Gly-L-Phe + H2O
benzoyl-Gly-Gly + L-Phe
benzoyl-Gly-L-alpha-hydroxy-beta-phenyllactate + H2O
?
-
-
-
-
?
benzoyl-Gly-L-Phe + H2O
benzoyl-Gly + L-Phe
benzoyl-Gly-phenyllactate + H2O
benzoyl-Gly-phenyllactate + ?
-
-
-
ir
Benzyloxycarbonyl-Ala-Phe + H2O
Benzyloxycarbonyl-Ala + Phe
-
-
-
ir
Benzyloxycarbonyl-Gly-Phe + H2O
Benzyloxycarbonyl-Gly + Phe
-
-
-
ir
benzyloxycarbonyl-Phe-Leu + H2O
benzyloxycarbonyl-Phe + Leu
-
-
-
ir
beta-actin (169-177) + H2O
?
-
weak substrate
-
-
?
big SAAS + H2O
?
-
good substrate
-
-
?
carbobenzoxy-Gly-Gly-L-Tyr + H2O
carbobenzoxy-Gly-Gly + L-Tyr
-
-
-
ir
carbobenzoxy-Gly-Gly-Leu + H2O
carbobenzoxy-Gly-Gly + Leu
-
-
-
ir
carbobenzoxy-Gly-Gly-Phe + H2O
carbobenzoxy-Gly-Gly + Phe
-
-
-
ir
carbobenzoxy-Gly-Gly-Val + H2O
carbobenzoxy-Gly-Gly + Val
-
-
-
ir
carbobenzoxy-Gly-L-Leu + H2O
carbobenzoxy-Gly + L-Leu
carbobenzoxy-Gly-L-Phe + H2O
carbobenzoxy-Gly + L-Phe
carbobenzoxy-Gly-L-Trp + H2O
carbobenzoxy-Gly + L-Trp
carbobenzyloxy-Gly-hippuryl-L-Phe + H2O
carbobenzyloxy-Gly-hippuric acid + L-Phe
-
-
-
ir
carboxypeptidase A5 C-terminus + H2O
?
-
requires an overnight incubation for a partial digestion by CPA4
-
-
?
cathepsin D (138-155) + H2O
?
-
weak substrate
-
-
?
chromogranin A (374-388) + H2O
?
-
good substrate
-
-
?
chromogranin A (374-390) + H2O
?
-
weak substrate
-
-
?
chromogranin B + H2O
?
-
good substrate
-
-
?
cinnamoyl-L-phenyllactate + H2O
cinnamic acid + L-phenyllactate
-
-
-
ir
clathrin light chain A C-terminus + H2O
?
-
weak substrate
-
-
?
dansylglycylglycyl-L-tryptophan + H2O
?
-
assay substrate
-
-
?
des-Asp1-angiotensin + H2O
?
-
partially cleaved in 2 h
-
-
?
dynorphin A8 + H2O
?
-
weak substrate
-
-
?
elongation factor 1 beta 2 N-terminus + H2O
?
-
good substrate
-
-
?
endothelin + H2O
?
-
removal of the C-terminal tryptophan
-
-
?
endothelin-1 + H2O
?
-
-
-
-
?
gamma-actin + H2O
?
-
weak substrate
-
-
?
Gly-L-Tyr + H2O
Gly + L-Tyr
glycyl-L-serylglycyl-L-seryl-N-(2,3-diazabicyclo[2.2.2]oct-2-en-1-ylmethyl)-L-asparaginylglycyl-L-seryl-L-tryptophan + H2O
glycyl-L-serylglycyl-L-seryl-N-(2,3-diazabicyclo[2.2.2]oct-2-en-1-ylmethyl)-L-asparaginylglycyl-L-serine + L-tryptophan
-
2,3-diazabicyclo[2.2.2]oct-2-ene-labeled asparagine as a fluorescent amino acid
-
-
?
hippuryl-DL-beta-phenylacetic acid + H2O
hippuric acid + DL-phenylacetic acid
-
-
-
-
?
hippuryl-DL-beta-phenyllactate + H2O
?
-
-
-
?
hippuryl-DL-beta-phenyllactic acid + H2O
hippuric acid + 3-phenyllactic acid
-
-
-
ir
hippuryl-DL-phenylalanine + H2O
hippuric acid + DL-phenylalanine
-
-
-
-
?
hippuryl-DL-phenyllactate + H2O
hippuric acid + DL-phenyllactate
hippuryl-DL-phenyllactic acid + H2O
hippuric acid + DL-phenyllactic acid
Hippuryl-L-Arg + H2O
Hippuric acid + L-Arg
-
-
-
ir
hippuryl-L-Phe + H2O
hippuric acid + L-Phe
hippuryl-L-Phe + H2O
hippuric acid + L-phenylalanine
the hydrolysis of the hippuryl-L-Phe molecule by carboxypeptidase A is investigated using both density functional theory and a hybrid quantum mechanical/molecular mechanical approach. The enzymatic reaction is found to proceed via a promoted water pathway with Glu270 serving as the general base and general acid. Free-energy calculations indicate that the first nucleophilic addition step is rate-limiting, with a barrier of 17.9 kcal/mol. Besides activating the zinc-bound water nucleophile, the zinc cofactor also serves as an electrophilic catalyst that stabilizes the substrate carbonyl oxygen during the formation of the tetrahedral intermediate. In the Michaelis complex, Arg127, rather than Zn(II), is responsible for the polarization of the substrate carbonyl and it also serves as the oxyanion hole
-
-
?
hippuryl-L-Phe + H2O
hippuric acid + Phe
hippuryl-L-phenylalanine + H2O
?
-
-
-
-
?
hippuryl-L-phenylalanine + H2O
hippuric acid + L-phenylalanine
hippuryl-L-phenyllactate + H2O
hippuric acid + L-phenyllactate
hippuryl-Phe + H2O
hippuric acid + Phe
kinetensin + H2O
?
-
-
-
-
?
L-beta-phenyllactate-alpha-((2-naphthoyl)amino)-cinnamoyl ester + H2O
L-beta-phenyllactate + alpha-((2-naphthoyl)amino) cinnamate
-
-
-
ir
L-beta-phenyllactate-alpha-(acetylamino)-cinnamoyl ester + H2O
L-beta-phenyllactate + alpha-(acetylamino)cinnamate
-
-
-
ir
L-beta-phenyllactate-alpha-(benzoylylamino)-cinnamoyl ester + H2O
L-beta-phenyllactate + alpha-(benzoylamino)-cinnamate
-
-
-
ir
Leu-enkephalin + H2O
?
-
partially cleaved in 2 h
-
-
?
little SAAS + H2O
?
-
small percentage of cleavage
-
-
?
Met-enkephalin + H2O
?
-
requires an overnight incubation for a partial digestion by CPA4
-
-
?
Met-enkephalin-L-Arg-L-Phe + H2O
Met-enkephalin-L-Arg + L-Phe
-
-
-
-
?
methotrexate-alpha-(1-naphthyl)alanine + H2O
methotrexate + (1-naphthyl)alanine
-
low activity
-
-
?
methotrexate-alpha-phenylalanine + H2O
methotrexate + phenylalanine
-
high activity
-
-
?
methotrexate-phenylalanine + H2O
methotrexate + phenylalanine
N-(2,3-diazabicyclo[2.2.2]oct-2-en-1-ylmethyl)-L-asparaginylglycyl-L-tryptophan + H2O
N-(2,3-diazabicyclo[2.2.2]oct-2-en-1-ylmethyl)-L-asparaginylglycine + L-tryptophan
-
2,3-diazabicyclo[2.2.2]oct-2-ene-labeled asparagine as a fluorescent amino acid
-
-
?
N-(2,3-diazabicyclo[2.2.2]oct-2-en-1-ylmethyl)-L-asparaginylglycylglycyl-L-tryptophan + H2O
N-(2,3-diazabicyclo[2.2.2]oct-2-en-1-ylmethyl)-L-asparaginylglycylglycine + L-tryptophan
-
2,3-diazabicyclo[2.2.2]oct-2-ene-labeled asparagine as a fluorescent amino acid
-
-
?
N-(2-furanacryloyl)-Phe-Phe + H2O
N-(2-furanacryloyl)-Phe + Phe
-
-
-
ir
N-(3-[2-furyl]acryloyl)-L-Phe-L-Phe + H2O
N-(3-[2-furyl]acryloyl)-L-Phe + L-Phe
-
-
-
-
?
N-(3-[2-furyl]acryloyl)-Phe-Phe
?
-
-
-
?
N-(3-[2-furyl]acryloyl)-Phe-Phe + H2O
?
substrate of carboxypeptidase activity assay
-
-
?
N-(3-[2-furyl]acryloyl)-Phe-Phe + H2O
N-(3-[2-furyl]acryloyl)-Phe + Phe
-
-
-
-
?
N-(4-methoxyphenyl-azoformyl)-L-Phe + H2O
?
-
-
-
?
N-(4-methoxyphenylazoformyl)-L-phenylalanine + H2O
?
-
-
-
-
?
N-(4-methoxyphenylazoformyl)-Phe + H2O
?
-
-
-
?
N-(4-methoxyphenylazoformyl)-Phe-OH + H2O
?
-
substrate for inhibition assay
-
-
?
N-(methoxyphenyl-azoformyl)-Phe-OH + H2O
?
-
-
-
-
?
N-(trans-3-indoleacryloyl)-L-Phe + H2O
trans-3-indoleacrylate + L-Phe
-
-
-
ir
N-acetyl-Gly-L-phenyllactic acid + H2O
N-acetyl-Gly + L-phenyllactic acid
-
-
-
ir
N-acetyl-L-aspartate
acetate + L-aspartate
-
-
-
-
?
N-acetyl-phenylalanyl-L-3-thiaphenylalanine + H2O
?
-
assay substrate
-
-
?
N-carbobenzoxy-Gly-Gly-L-Leu + H2O
N-carbobenzoxy-Gly-Gly + L-Leu
-
-
-
ir
N-carbobenzoxy-Gly-Gly-L-Phe + H2O
N-carbobenzoxy-Gly-Gly + L-Phe
-
-
-
ir
N-carbobenzoxy-Gly-L-Phe + H2O
N-carbobenzoxy-Gly + L-Phe
-
-
-
ir
N-carbobenzoxy-Gly-L-Tyr + H2O
N-carbobenzoxy-Gly + L-Tyr
-
-
-
ir
N-[3-(2-furyl)acryloyl]-Phe-Phe + H2O
?
-
-
-
-
?
N-[3-(2-furyl)acryloyl]-Phe-Phe + H2O
N-[3-(2-furyl)acryloyl]-Phe + Phe
-
-
-
?
N-[3-(2-furyl)]acryloyl-L-Phe-L-Phe + H2O
N-[3-(2-furyl)]acryloyl-L-Phe + L-Phe
-
-
-
?
N-[4-methoxyphenylazoformyl]-Phe-OH + H2O
?
N2acetyl-N-(2,3-diazabicyclo[2.2.2]oct-2-en-1-ylmethyl)-L-asparaginyl-L-tryptophan + H2O
N2-acetyl-N-(2,3-diazabicyclo[2.2.2]oct-2-en-1-ylmethyl)-L-asparagine + L-tryptophan
-
2,3-diazabicyclo[2.2.2]oct-2-ene-labeled asparagine as a fluorescent amino acid
-
-
?
O-(trans-4-chlorocinnamoyl)-L-beta-phenyllactate + H2O
trans-4-chlorocinnamic acid + L-phenyllactic acid
-
-
-
?
O-(trans-4-chlorocinnamoyl)-L-phenyllactic acid + H2O
trans-4-chlorocinnamic acid + L-phenyllactic acid
-
-
-
-
?
O-(trans-p-chlorocinnamoyl)-L-beta-phenyllactate + H2O
?
O-(trans-p-chlorocinnamoyl)-L-phenylacetic acid + H2O
?
-
-
-
?
O-(trans-p-chlorocinnamoyl)-L-phenyllactic acid + H2O
?
-
-
?
O-(trans-p-chlorocinnamyl)-L-beta-phenyllactate + H2O
?
-
-
-
?
ochratoxin A + H2O
ochratoxin alpha + L-beta-phenylalanine
p-nitrophenyl acetate + H2O
nitrophenolate + acetate
-
-
-
-
?
peptidyl-L-amino acid + H2O
?
-
rapid release: Tyr, Phe, Trp, Leu, Ile, Thr, Gln, His, Ala, Val, homoserine, slow release: Asn, Ser, Lys, MetSO2, very slow release: Gly, Asp, Glu, CysSO3, S-carboxymethylcysteine, not released: Pro, hydroxyproline, Arg, enzyme generally releases C-terminal amino acids, with the exception of C-terminal arginine, lysine and proline
-
-
?
peptidylprolyl isomerase A (118-129) + H2O
?
-
good substrate
-
-
?
peptidylprolyl isomerase A (23-39) + H2O
?
-
weak substrate
-
-
?
peptidylprolyl isomerase A (26-39) + H2O
?
-
weak substrate
-
-
?
peptidylprolyl isomerase A (84-100) + H2O
?
-
weak substrate
-
-
?
peptidylprolyl isomerase A (84-92) + H2O
?
-
weak substrate
-
-
?
peroxiredoxin V N-terminus + H2O
?
-
good substrate
-
-
?
Phe-Asn-Arg-Pro-Val + H2O
?
used as substrate in the activity assay
-
-
?
Phe-Asn-Arg-Pro-Val-Asp + H2O
?
used as substrate in the activity assay
-
-
?
Phe-Asn-Arg-Pro-Val-Val + H2O
?
used as substrate in the activity assay
-
-
?
procholecystokinin (46-62) + H2O
?
-
weak substrate
-
-
?
procholecystokinin (46-63) + H2O
?
-
weak substrate
-
-
?
proenkenphalin octapeptide + H2O
?
-
weak substrate
-
-
?
proenkephalin + H2O
?
-
good substrate
-
-
?
propeptidyl-amidating monooxygenase + H2O
?
-
good substrate
-
-
?
proteasome subunit beta type 6 (34-41) + H2O
?
-
weak substrate
-
-
?
protein PEN + H2O
?
-
good substrate
-
-
?
protein PEN-20 + H2O
?
-
good substrate
-
-
?
provasopressin (151-end) + H2O
?
-
weak substrate
-
-
?
ribosomal protein S21 C-terminus + H2O
?
3.4.17.1 carboxypeptidase A
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