3.4.17.11: glutamate carboxypeptidase
This is an abbreviated version!
For detailed information about glutamate carboxypeptidase, go to the full flat file.
Word Map on EC 3.4.17.11
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3.4.17.11
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methotrexate
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prodrugs
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high-dose
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antibody-directed
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leucovorin
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hdmtx
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methotrexate-induced
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gene-directed
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naaladase
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gdept
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antibody-enzyme
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medicine
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anti-cea
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anti-carcinoembryonic
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prodrug-activating
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gcpii
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2-pmpa
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n-acetyl-aspartyl-glutamate
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dampa
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drug development
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diagnostics
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pharmacology
- 3.4.17.11
- methotrexate
-
prodrugs
-
high-dose
-
antibody-directed
- leucovorin
-
hdmtx
-
methotrexate-induced
-
gene-directed
- naaladase
-
gdept
-
antibody-enzyme
- medicine
-
anti-cea
-
anti-carcinoembryonic
-
prodrug-activating
- gcpii
- 2-pmpa
-
n-acetyl-aspartyl-glutamate
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dampa
- drug development
- diagnostics
- pharmacology
Reaction
release of C-terminal glutamate residues from a wide range of N-acylating moieties, including peptidyl, aminoacyl, benzoyl, benzyloxycarbonyl, folyl and pteroyl groups =
Synonyms
carboxypeptidase G, carboxypeptidase G1, carboxypeptidase G2, CPDG2, CPG2, folate hydrolase G2, glucarpidase, glutamate carboxypeptidase, glutamyl carboxypeptidase, N-pteroyl-L-glutamate hydrolase, pteroylmonoglutamic acid hydrolase G2
ECTree
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Natural Substrates Products
Natural Substrates Products on EC 3.4.17.11 - glutamate carboxypeptidase
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REACTION DIAGRAM
(2S,2'S)-2,2'-(pentane-1,5-diylbis[oxy[(11S,11aS)-11-hydroxy-7-methoxy-5-oxo-2,3,11,11a-tetrahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-8,10(5H)-diyl]carbonyloxymethanediylbenzene-4,1-diylcarbamoylimino])dipentanedioic acid + 2 H2O
(11aS,11a'S)-8,8'-[pentane-1,5-diylbis(oxy)]bis(7-methoxy-1,2,3,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one) + ?
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?
(2S,2'S)-2,2'-(pentane-1,5-diylbis[oxy[(11S,11aS)-11-hydroxy-7-methoxy-5-oxo-2,3,11,11a-tetrahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-8,10(5H)-diyl]carbonyloxymethanediylbenzene-4,1-diyloxycarbonylimino])dipentanedioic acid + 2 H2O
3-hydroxybenzyl 4-hydroxybenzyl (11S,11aS,11'S,11a'S)-8,8'-[pentane-1,5-diylbis(oxy)]bis(11-hydroxy-7-methoxy-5-oxo-2,3,11,11a-tetrahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-10(5H)-carboxylate) + 2 N-carboxy-L-glutamate
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?
(4-[bis(2-bromoethyl)amino]-3,5-difluorobenzoyl)-L-glutamic acid + H2O
4-[bis(2-bromoethyl)amino]-3,5-difluorobenzoic acid + L-glutamate
(4-[bis(2-iodoethyl)amino]-3,5-difluorobenzoyl)-L-glutamic acid + H2O
4-[bis(2-iodoethyl)amino]-3,5-difluorobenzoic acid + L-glutamate
(6R,S)-leucovorin + H2O
N-(6R,S)-5-formyl-5,6,7,8-tetrahydropteroic acid + L-glutamate
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inactivation of the antitumor drug
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?
4-([bis(2-iodoethyl)amino]-phenyl)oxycarbonyl-L-glutamic acid + H2O
4-[bis(2-iodoethyl)amino]-phenylcarbonate + L-glutamate
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substrate can be used as a prodrug that is hydrolyzed to yield the active drug in an antibody directed enzyme prodrug therapy
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?
7-hydroxy-methotrexate + H2O
7-hydroxy-4-amino-4-deoxy-N10-methylpteroic acid + L-glutamate
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?
diethylstilbestrol-glutamate + H2O
diethylstilbestrol + L-glutamate
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the water soluble substrate can be used as a prodrug that is hydrolyzed to yield the active drug in an antibody directed enzyme prodrug therapy
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?
methotrexate + H2O
4-amino-4-deoxy-N10-methylpteroic acid + L-glutamate
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highly reduced clearance of the drug in enzyme-defective patients leads to severe neutropenia, mucositis, nephrotoxicity, neurotoxicity, and elevation of liver enzymes in plasma
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?
methotrexate + H2O
4-[(2,4-diamino-6-(pteridinyl)methyl)-methylamino]-benzoic acid + L-glutamate
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related toxicity, overview, rapid inactivation of methotrexate by CPDG2, the product DAMPA is eliminated more raoidly than methotrexate
i.e. DAMPA
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?
N-([4-[([[(11S,11aS)-11-hydroxy-7,8-dimethoxy-5-oxo-2,3,11,11a-tetrahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepin-10(5H)-yl]carbonyl]oxy)methyl]phenoxy]carbonyl)-L-glutamic acid + H2O
(11aS)-7,8-dimethoxy-1,2,3,10,11,11a-hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one + ?
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?
N-([4-[([[(11S,11aS)-11-hydroxy-7,8-dimethoxy-5-oxo-2,3,11,11a-tetrahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepin-10(5H)-yl]carbonyl]oxy)methyl]phenyl]carbamoyl)-L-glutamic acid + H2O
? + L-glutamate
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?
4-[bis(2-bromoethyl)amino]-3,5-difluorobenzoic acid + L-glutamate
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a difluorinated prodrug
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?
(4-[bis(2-bromoethyl)amino]-3,5-difluorobenzoyl)-L-glutamic acid + H2O
4-[bis(2-bromoethyl)amino]-3,5-difluorobenzoic acid + L-glutamate
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a difluorinated prodrug
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?
4-[bis(2-iodoethyl)amino]-3,5-difluorobenzoic acid + L-glutamate
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a difluorinated prodrug
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?
(4-[bis(2-iodoethyl)amino]-3,5-difluorobenzoyl)-L-glutamic acid + H2O
4-[bis(2-iodoethyl)amino]-3,5-difluorobenzoic acid + L-glutamate
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a difluorinated prodrug
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?
?
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synthesis and biological evaluation of pyrrolo[2,1-c][1,4]benzodiazepine prodrugs for use in antibody-directed enzyme prodrug therapy, overview
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additional information
?
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specifically cleaves terminal glutamic acid amines
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additional information
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effects of carboxypeptidase G2 administration to patients with methotrexate-induce renal failure, overview
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additional information
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enzyme is used in enzyme prodrug therapy to treat human breast cancer, the enzyme catalyzes the activation of the di- and trifluorinated prodrugs, overview
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additional information
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specifically cleaves terminal glutamic acid amines
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additional information
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CPG2 cleaves folic acid to pteroic acid and activates a range of bifunctional alkylating agent and antibiotic prodrugs
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additional information
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enzyme is used in enzyme prodrug therapy to treat human breast cancer, the enzyme catalyzes the activation of the di- and trifluorinated prodrugs, overview
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?