Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
(2S,6S)-2,6-diaminoheptanedioate
meso-diaminoheptanedioate
-
-
-
?
DL-3-fluoro-2,6-diaminopimelic acid
tetrahydrodipicolinic acid + HF
-
rapid elimination, enamine product is formed which spontaneously cyclizes to tetrahydrodipicolinic acid
-
?
LL-2,6-Diaminoheptanedioate
?
LL-2,6-Diaminoheptanedioate
meso-Diaminoheptanedioate
LL-2,6-diaminoheptanedioate
meso-diaminopimelate
LL-3-fluoro-2,6-diaminopimelic acid
tetrahydrodipicolinic acid + HF
-
slow elimination of HF
-
?
LL-oxa-diaminopimelic acid
meso-oxa-diaminopimelic acid
-
-
-
?
meso-diaminoheptanedioate
LL-2,6-diaminoheptanedioate
additional information
?
-
LL-2,6-Diaminoheptanedioate

?
-
enzyme active in two of three possible pathways for synthesis of L-Lys, acetyltransferase pathway and succinyltransferase pathway. Not active in D-diaminopimelate dehydrogenase variant
-
-
?
LL-2,6-Diaminoheptanedioate
?
-
enzyme of Lys biosynthesis
-
-
?
LL-2,6-Diaminoheptanedioate
?
-
enzyme of Lys biosynthesis
-
-
?
LL-2,6-Diaminoheptanedioate
?
-
enzyme of the diaminopimelic acid pathway for biosynthesis of Lys
-
-
?
LL-2,6-Diaminoheptanedioate

meso-Diaminoheptanedioate
-
-
-
-
r
LL-2,6-Diaminoheptanedioate
meso-Diaminoheptanedioate
-
-
-
?
LL-2,6-Diaminoheptanedioate
meso-Diaminoheptanedioate
-
-
-
?
LL-2,6-Diaminoheptanedioate
meso-Diaminoheptanedioate
-
-
-
?
LL-2,6-Diaminoheptanedioate
meso-Diaminoheptanedioate
-
-
-
?
LL-2,6-Diaminoheptanedioate
meso-Diaminoheptanedioate
-
-
-
-
r
LL-2,6-Diaminoheptanedioate
meso-Diaminoheptanedioate
Chlamydomonas sp.
-
-
-
?
LL-2,6-Diaminoheptanedioate
meso-Diaminoheptanedioate
-
-
-
?
LL-2,6-Diaminoheptanedioate
meso-Diaminoheptanedioate
-
-
-
r
LL-2,6-Diaminoheptanedioate
meso-Diaminoheptanedioate
-
-
-
r
LL-2,6-Diaminoheptanedioate
meso-Diaminoheptanedioate
-
-
-
?
LL-2,6-Diaminoheptanedioate
meso-Diaminoheptanedioate
-
-
-
?
LL-2,6-Diaminoheptanedioate
meso-Diaminoheptanedioate
-
-
-
?
LL-2,6-Diaminoheptanedioate
meso-Diaminoheptanedioate
-
-
-
?
LL-2,6-Diaminoheptanedioate
meso-Diaminoheptanedioate
-
-
-
?
LL-2,6-Diaminoheptanedioate
meso-Diaminoheptanedioate
-
-
-
?
LL-2,6-Diaminoheptanedioate
meso-Diaminoheptanedioate
-
-
-
?
LL-2,6-Diaminoheptanedioate
meso-Diaminoheptanedioate
-
-
-
?
LL-2,6-Diaminoheptanedioate
meso-Diaminoheptanedioate
-
-
-
?
LL-2,6-Diaminoheptanedioate
meso-Diaminoheptanedioate
-
-
-
?
LL-2,6-Diaminoheptanedioate
meso-Diaminoheptanedioate
-
-
-
-
r
LL-2,6-Diaminoheptanedioate
meso-Diaminoheptanedioate
-
-
-
?
LL-2,6-Diaminoheptanedioate
meso-Diaminoheptanedioate
-
-
-
?
LL-2,6-Diaminoheptanedioate
meso-Diaminoheptanedioate
-
-
-
-
?
LL-2,6-Diaminoheptanedioate
meso-Diaminoheptanedioate
-
-
-
?
LL-2,6-Diaminoheptanedioate
meso-Diaminoheptanedioate
-
-
-
r
LL-2,6-Diaminoheptanedioate
meso-Diaminoheptanedioate
-
-
-
r
LL-2,6-Diaminoheptanedioate
meso-Diaminoheptanedioate
-
-
-
-
?
LL-2,6-Diaminoheptanedioate
meso-Diaminoheptanedioate
-
-
-
-
?
LL-2,6-Diaminoheptanedioate
meso-Diaminoheptanedioate
-
-
-
?
LL-2,6-Diaminoheptanedioate
meso-Diaminoheptanedioate
-
-
-
?
LL-2,6-Diaminoheptanedioate
meso-Diaminoheptanedioate
-
-
-
?
LL-2,6-Diaminoheptanedioate
meso-Diaminoheptanedioate
-
-
-
?
LL-2,6-Diaminoheptanedioate
meso-Diaminoheptanedioate
-
-
-
?
LL-2,6-Diaminoheptanedioate
meso-Diaminoheptanedioate
-
-
-
?
LL-2,6-Diaminoheptanedioate
meso-Diaminoheptanedioate
-
-
-
?
LL-2,6-Diaminoheptanedioate
meso-Diaminoheptanedioate
-
r, between 25°C and 45°C at pH 7.0, the equilibrium mixture contains 65% meso-isomer and 35% LL-isomer
-
?
LL-2,6-Diaminoheptanedioate
meso-Diaminoheptanedioate
-
-
-
?
LL-2,6-Diaminoheptanedioate
meso-Diaminoheptanedioate
-
-
-
?
LL-2,6-Diaminoheptanedioate
meso-Diaminoheptanedioate
-
-
-
?
LL-2,6-Diaminoheptanedioate
meso-Diaminoheptanedioate
-
-
-
?
LL-2,6-Diaminoheptanedioate
meso-Diaminoheptanedioate
-
-
-
?
LL-2,6-diaminoheptanedioate

meso-diaminopimelate
-
stereo-inversion
-
-
?
LL-2,6-diaminoheptanedioate
meso-diaminopimelate
stereo-conversion, the product complex (Enzyme/meso-diaminopimelate) is less stable than the reactant complex (Enzyme/LL-diaminopimelate)
-
-
r
LL-2,6-diaminoheptanedioate
meso-diaminopimelate
stereo-inversion
the meso-isomer of diaminopimelic acid, a precursor of L-lysine, is a key component of the pentapeptide linker in bacterial peptidoglycan
-
?
LL-2,6-diaminoheptanedioate
meso-diaminopimelate
stereo-inversion
the meso-isomer of diaminopimelic acid, a precursor of L-lysine, is a key component of the pentapeptide linker in bacterial peptidoglycan
-
?
meso-diaminoheptanedioate

LL-2,6-diaminoheptanedioate
-
-
-
r
meso-diaminoheptanedioate
LL-2,6-diaminoheptanedioate
-
-
-
r
additional information

?
-
ligand binding to a cleft between the two domains of the enzyme is accompanied by domain closure with strictly conserved cysteine residues, Cys99 and Cys254, positioned to perform acid/base catalysis via a carbanion stabilization mechanism on the stereogenic alpha-carbon atom of the amino acid. Stereochemical control in catalysis is achieved by means of a highly symmetric catalytic site that can accommodate both the L and D stereogenic centers of DAP at the proximal site, whereas specific interactions at the distal site require only the L configuration
-
-
?
additional information
?
-
-
ligand binding to a cleft between the two domains of the enzyme is accompanied by domain closure with strictly conserved cysteine residues, Cys99 and Cys254, positioned to perform acid/base catalysis via a carbanion stabilization mechanism on the stereogenic alpha-carbon atom of the amino acid. Stereochemical control in catalysis is achieved by means of a highly symmetric catalytic site that can accommodate both the L and D stereogenic centers of DAP at the proximal site, whereas specific interactions at the distal site require only the L configuration
-
-
?
additional information
?
-
-
Chlamydia trachomatis dapF encodes a bifunctional enzyme capable of both D-glutamate racemase, EC 5.1.1.3, and diaminopimelate epimerase activities. DAP and glutamate appear to be competitive substrates, indicating that they share an active site despite the racemase reaction requiring the pyridoxal 5'-phosphate cofactor
-
-
?
additional information
?
-
no activity with DD-2,6-diaminoheptanedioate. Development of a simple method using thin-layer chromatography, in methanol/water (64:36) and with ninhydrin detection, and chiral column chromatography to allow preparation of pure diaminopimelate isomers and detect products, respectively, overview
-
-
?
additional information
?
-
no activity with DD-2,6-diaminoheptanedioate. Development of a simple method using thin-layer chromatography, in methanol/water (64:36) and with ninhydrin detection, and chiral column chromatography to allow preparation of pure diaminopimelate isomers and detect products, respectively, overview
-
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
LL-2,6-Diaminoheptanedioate
?
LL-2,6-Diaminoheptanedioate
meso-Diaminoheptanedioate
LL-2,6-diaminoheptanedioate
meso-diaminopimelate
additional information
?
-
-
Chlamydia trachomatis dapF encodes a bifunctional enzyme capable of both D-glutamate racemase, EC 5.1.1.3, and diaminopimelate epimerase activities. DAP and glutamate appear to be competitive substrates, indicating that they share an active site despite the racemase reaction requiring the pyridoxal 5'-phosphate cofactor
-
-
?
LL-2,6-Diaminoheptanedioate

?
-
enzyme active in two of three possible pathways for synthesis of L-Lys, acetyltransferase pathway and succinyltransferase pathway. Not active in D-diaminopimelate dehydrogenase variant
-
-
?
LL-2,6-Diaminoheptanedioate
?
-
enzyme of Lys biosynthesis
-
-
?
LL-2,6-Diaminoheptanedioate
?
-
enzyme of Lys biosynthesis
-
-
?
LL-2,6-Diaminoheptanedioate
?
-
enzyme of the diaminopimelic acid pathway for biosynthesis of Lys
-
-
?
LL-2,6-Diaminoheptanedioate

meso-Diaminoheptanedioate
-
-
-
-
r
LL-2,6-Diaminoheptanedioate
meso-Diaminoheptanedioate
-
-
-
-
r
LL-2,6-Diaminoheptanedioate
meso-Diaminoheptanedioate
-
-
-
r
LL-2,6-Diaminoheptanedioate
meso-Diaminoheptanedioate
-
-
-
r
LL-2,6-Diaminoheptanedioate
meso-Diaminoheptanedioate
-
-
-
-
r
LL-2,6-Diaminoheptanedioate
meso-Diaminoheptanedioate
-
-
-
r
LL-2,6-Diaminoheptanedioate
meso-Diaminoheptanedioate
-
-
-
r
LL-2,6-diaminoheptanedioate

meso-diaminopimelate
-
stereo-inversion
-
-
?
LL-2,6-diaminoheptanedioate
meso-diaminopimelate
stereo-conversion, the product complex (Enzyme/meso-diaminopimelate) is less stable than the reactant complex (Enzyme/LL-diaminopimelate)
-
-
r
LL-2,6-diaminoheptanedioate
meso-diaminopimelate
stereo-inversion
the meso-isomer of diaminopimelic acid, a precursor of L-lysine, is a key component of the pentapeptide linker in bacterial peptidoglycan
-
?
LL-2,6-diaminoheptanedioate
meso-diaminopimelate
stereo-inversion
the meso-isomer of diaminopimelic acid, a precursor of L-lysine, is a key component of the pentapeptide linker in bacterial peptidoglycan
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
(2-(4-amino-4-carboxybutyl) aziridine-2-carboxylic acid)
AziDAP
1,2-benzisothiazolidine 3-one
30 nM, complete inhibition
2-(4-amino-4-carboxybutyl)-aziridine-2-carboxylate
substrate mimic, irreversible inhibition
2-(4-amino-4-carboxybutyl)aziridine-2-carboxylic acid
-
irreversible
2-nitro-5-thiocyanatobenzoate
30 nM, complete inhibition
3-Chlorodiaminopimelate
-
the inhibitor is converted to a tight-binding transition state analog at the active site of this enzyme
3-fluoro analogs of diaminopimelate
-
potent competitive inhibitors
-
4-Oxo-1,2,3,4-tetrahydro-pyridine-2,6-dicarboxylic acid
-
very poor inhibitor
5,5'-dithiobis(2-nitrobenzoic acid)
30 nM, complete inhibition
acetone
inactivation by 50% acetone
dilithium (2Z,6S)-2,6-diamino-4-oxohept-2-enedioate
-
competitive, IC50: 0.5 mM
DL-aziridino analogues of diaminoheptanedioate
DL-aziridino diaminopimelic acid, irreversible inhibitor
DL-aziridino-diaminopimelate
product-like inhibitor, inhibitor mimics the natural substrate, the methylene carbon of the aziridine ring of the 2 diastereomeric inhibitors is covalently bonded to the sulfur atom of Cys73 or Cys217 after the nucleophilic attack of the sulfur on the aziridine ring that irreversibly inhibits the enzyme
Lanthionine isomers
-
-
-
Lanthionine sulfoxide
-
-
LL-aziridino analogues of diaminoheptanedioate
LL-aziridino diaminopimelic acid, irreversible inhibitor
LL-aziridino-diaminopimelate
reactant-like inhibitor, inhibitor mimics the natural substrate, the methylene carbon of the aziridine ring of the 2 diastereomeric inhibitors is covalently bonded to the sulfur atom of Cys73 or Cys217 after the nucleophilic attack of the sulfur on the aziridine ring that irreversibly inhibits the enzyme
N-Aminodiaminopimelate
-
-
N-Hydroxydiaminopimelate
-
-
Phosphonate analogs of diaminopimelate
-
-
-
hydroxylamine

-
no inhibition
hydroxylamine
-
no inhibition
iodoacetamide

-
half-life for inactivation with 0.25 mM iodoacetamide is 9.6 min
Semicarbazide

-
-
Semicarbazide
-
no inhibition
additional information

-
-
-
additional information
-
none of the following compounds shows significant inhibition: (2S)-2-amino-3-(4-carboxyimidazol-1-yl)propanoic acid, (2S,5'R)-2-amino-3-(3-carboxy-2-isoxazolin-5-yl)propanoic acid and its 5'S diastereomer, 2-isoxazoline-3-carboxylic acid, and 2-isoxazoline-3,5-dicarboxylic acid
-
additional information
-
no inhibition by deoxypyridioxine
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.