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IUBMB Comments In the entry, "phthalyl" is used to mean "2-carboxybenzoyl". The enzyme from Xanthobacter agilis hydrolyses phthalylated amino acids, peptides, β-lactams, aromatic and aliphatic amines. The substituent on nitrogen may be an alkyl group, but may also be complex, giving an amino acid or peptide derivative. Substitutions on the phthalyl ring include 6-F, 6-NH2 ortho to the carboxy group attached to the amine. No cofactors are required
Synonyms
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Amidase, phthalyl
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o-Phthalyl amidase
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A phthalylamide + H2O = phthalic acid + a substituted amine
A phthalylamide + H2O = phthalic acid + a substituted amine
mechanism
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A phthalylamide + H2O = phthalic acid + a substituted amine
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hydrolysis of linear amides
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Phthalyl-amide amidohydrolase
In the entry, "phthalyl" is used to mean "2-carboxybenzoyl". The enzyme from Xanthobacter agilis hydrolyses phthalylated amino acids, peptides, beta-lactams, aromatic and aliphatic amines. The substituent on nitrogen may be an alkyl group, but may also be complex, giving an amino acid or peptide derivative. Substitutions on the phthalyl ring include 6-F, 6-NH2, 3-OH, and a nitrogen in the aromatic ring ortho to the carboxy group attached to the amine. No cofactors are required
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2-Carboxybenzoylamine-D-Phe-L-Ala
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Substrates: -
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2-Carboxybenzoylamine-D-phenylglycine-methylester
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Substrates: -
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2-Carboxybenzoylamine-L-Phe-L-Ala
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Substrates: -
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7-Phthalamido-3-chloro-4-carboxy-1-carbadethioceph-3-em
Aspartame + phthalic acid
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Substrates: i.e. phthalamindo carbacephem
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N-Phthalamido-L-Asp-L-Phe methyl ester
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Substrates: -
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o-Phthalyl carbacephem
Loracarbef + phthalic acid
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Substrates: -
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[4-[(2-Carboxybenzoyl)amino]-1H-imidazol-1-yl]octanoic acid
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Substrates: -
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additional information
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additional information
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Substrates: substrate specificity: hydrolyzes phthalylated amino acids, peptides, beta-lactams, aromatic and aliphatic amines. Substitutions allowed on the phthalyl group include 6-F, 6-NH2, 3-OH, and a nitrogen in the aromatic ring ortho to the carboxyl group
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additional information
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Substrates: broad specificity for o-phthalylated amides, absolute requirement for the o-phthalyl protecting group
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p-hydroxymercuribenzoate
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0.16
2-carboxybenzoylamine-D-Phe-L-Ala
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0.56
2-carboxybenzoylamine-D-phenylglycine-methylester
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0.23
2-carboxybenzoylamine-L-Phe-L-Ala
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0.9
7-Phthalamido-3-chloro-4-carboxy-1-carbadethioceph-3-em
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additional information
additional information
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1.8
2-carboxybenzoylamine-D-Phe-L-Ala
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4.7
2-carboxybenzoylamine-D-phenylglycine-methylester
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2.3
2-carboxybenzoylamine-L-Phe-L-Ala
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brenda
Highest Expressing Human Cell Lines
Filter by:
Cell Line Links
Gene Links
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PHAM_XANAG
453
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49856
Swiss-Prot
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49000
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1 * 49000, SDS-PAGE
49724
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1 * 49724, calculation from nucleotide sequence
49900
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electrospray mass spectrometry
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monomer
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1 * 49000, SDS-PAGE
monomer
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1 * 49724, calculation from nucleotide sequence
monomer
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1 * 49900-50000, SDS-PAGE
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25
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below, pH 8.2, 48 h, 10% loss of activity
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pH 8.2, 48 h, 20% loss of activity
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pH 8.2, 48 h, 70% loss of activity
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pH-stability and temperature-stability is improved significantly by increasing ionic strength of the buffer
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stability is dependent on the high ionic strength of the buffer
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the enzyme stability is optimal at salt concentrations of 0.2 M and above
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the substrate phthalimido carbacephem stablilizes the enzyme
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expression in Streptomyces lividans and Escherichia coli
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synthesis
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alternative chemical route in removing the phthalimido protecting group
synthesis
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selective deprotection of phthalyl protected amines
synthesis
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the enzyme catalyzes removal of the phthalyl group from a wide variety of phthalyl-containing compounds with improved yields over processes, exhibits stereochemical selectivity, and eliminates the need for harsh conditions to remove the protecting group
synthesis
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one-step synthesis of the antibiotic loracarbef
synthesis
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synthesis of aspartame
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Black, T.D.; Briggs, B.S.; Evans, R.; Muth, W.L.; Vangala, S.; Zmijewski, M.J.
o-Phthalyl amidase in the synthesis of loracarbef: process development using this novel biocatalyst
Biotechnol. Lett.
18
875-880
1996
Xanthobacter agilis
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brenda
Costello, C.A.; Kreuzman, A.J.; Zmijewski, M.J.
Selective deprotection of phthalyl protected amines
Tetrahedron Lett.
37
7469-7472
1996
Xanthobacter agilis
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brenda
Briggs, B.S.; Kreuzman, A.J.; Whitesitt, C.; Yeh, W.K.; Zmijewski, M.
Discovery, purification, and properties of o-phthalyl amidase from Xanthobacter agilis
J. Mol. Catal. , B Enzym.
2
53-69
1996
Xanthobacter agilis
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brenda
Briggs, B.S.; Zmijewski Jr., M.J.
Enzyme from microbial sources: phthalyl amidase
United States Patent 5,445,959
1995
Xanthobacter agilis
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brenda
Queener, S.W.; Zock, J.M.
Genes encoding and method of expressing a novel enzyme phthalyl amidase
United States Patent 5,543,497
1996
Xanthobacter agilis
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brenda
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