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2.3.2.B14: L,D-transpeptidase

This is an abbreviated version!
For detailed information about L,D-transpeptidase, go to the full flat file.

Word Map on EC 2.3.2.B14

Reaction

Generates 3->3 cross-links in peptidoglycan, catalyzing the cleavage of the mDap(3)-D-Ala4 bond of a tetrapeptide donor stem and the formation of a bond between the carbonyl of mDap3 of the donor stem and the side chain of mDap3 of the acceptor stem. =

Synonyms

CLIBASIA_01175, IprQ, L,D-transpeptidase, L,D-transpeptidase 2, L,D-transpeptidase 5, LdtB, LdtBS, LdtF, Ldtfm, Ldtfm217, Ldtfs, LdtMt1, LdtMt2, LdtP, MAB_1530, MAB_3165c, MT0125, MT0501, MT2594, Rv1433, Rv2518c, transpeptidase, YcbB

ECTree

     2 Transferases
         2.3 Acyltransferases
             2.3.2 Aminoacyltransferases
                2.3.2.B14 L,D-transpeptidase

Inhibitors

Inhibitors on EC 2.3.2.B14 - L,D-transpeptidase

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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(4R,5S,6S)-3-[[(3S,5R)-5-(aminomethyl)oxolan-3-yl]sulfanyl]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
compound identified by virtual screening, interacts with residues Arg242 and Gly304
(4R,6S)-3-[[(3R,5R)-5-(aminomethyl)oxolan-3-yl]sulfanyl]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
2-[(2S,3S)-2-(2H-1,3-benzodioxol-5-yl)-1-(3-fluoro-4-methylphenyl)-4-oxoazetidin-3-yl]-5-nitro-1H-isoindole-1,3(2H)-dione
inhibitor identified by virtual screening, demonstrates close hydrogen bond interaction between the ligand and two active site residues Asn303 and Cys305, shows the highest binding free energy observed
2-[(2S,3S)-2-(4-fluorophenyl)-1-(3-methylphenyl)-4-oxoazetidin-3-yl]-5-nitro-1H-isoindole-1,3(2H)-dione
6-aminopenicillanic acid
high degree of Cys354 modification, occurrence of a possible coupling reaction
amoxicillin
ampicillin
aztreonam
-
no acylation observed
biapenem
carbapenem beta-32
-
-
cefapirin
-
formation of a covalent comple that undergoes non-hydrolytic fragmentation, resulting in an adduct in which the C3' leaving group is lost
cefdinir
doripenem and cefdinir exhibit synergy against Mycobacterium abscessus
cefotaxime
ceftriaxone
cephalexin
minimal inhibition; minimal inhibition
cephalothin
doripenem
ertapenem
faropenem
faropenem daloxate
high degree of Cys354 modification, fast degradation following the initial acylation event
Imipenem
meropenem
moxalactam
-
no acylation observed
Oxacillin
panipenem
panipenem is not degraded after binding. The presence of the 1-beta-methyl group in carbapenems is related to the ligand affinity of LdtB and the presence of the Y308 and Y318 residues in LdtB stabilizes the conformation of the LdtB-carbepenem adduct
penicillin-G
no covalent adduct observed
piperacillin
pivmecillinam
no covalent adduct observed
sulopenem
-
formation of a covalent comple that undergoes non-hydrolytic fragmentation, yielding LdtB acylated with a 3-hydroxybutanoate fragment
tebipenem
ticarcillin
-
formation of a covalent comple that undergoes non-hydrolytic fragmentation
ZINC02475683
simulation of complex with isoform IprQ. The DELTAG# for the acylation is calculated as 28.26 kcal/mol
ZINC03784242
simulation of complex with isoform IprQ. The DELTAG# for the acylation is calculated as 27.86 kcal/mol
ZINC03788344
simulation of complex with isoform IprQ. The DELTAG# for the acylation is calculated as 13.67 kcal/mol
ZINC03791246
simulation of complex with isoform IprQ. The DELTAG# for the acylation is calculated as 22.88 kcal/mol
additional information
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