A1880
(±)-2-Aminopimelic acid
≥99%
Synonym(s):
(±)-2-Aminoheptanedioic acid
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About This Item
Empirical Formula (Hill Notation):
C7H13NO4
CAS Number:
Molecular Weight:
175.18
EC Number:
211-011-7
UNSPSC Code:
12352200
PubChem Substance ID:
Beilstein/REAXYS Number:
1722015
MDL number:
assay
≥99%
SMILES string
NC(CCCCC(O)=O)C(O)=O
InChI
1S/C7H13NO4/c8-5(7(11)12)3-1-2-4-6(9)10/h5H,1-4,8H2,(H,9,10)(H,11,12)
InChI key
JUQLUIFNNFIIKC-UHFFFAOYSA-N
Biochem/physiol Actions
2-Aminopimelic acid may be used to create peptides that are antibacterial agents that inhibit diaminopimelic acid biosynthesis required for cell wall biosynthesis.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Regulatory Information
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Peptides containing 2-aminopimelic acid. Synthesis and study of in vitro effects on bacterial cells.
P Le Roux et al.
International journal of peptide and protein research, 37(2), 103-111 (1991-02-01)
Taking advantage of the peptide transport strategy, we have designed and synthesized several new peptides containing 2-aminopimelic acid (Apm), an inhibitor of the diaminopimelate pathway in bacteria: L-Lys-ambo-Apm, ambo-Apm-L-Lys, L-Lys-L-Ala-ambo-Apm, ambo-Apm-L-Ala-L-Lys, L-Ala(Cl)-ambo-Apm and ambo-Apm-L-Ala(Cl). In the two latter cases, Apm
Peptides of 2-aminopimelic acid: antibacterial agents that inhibit diaminopimelic acid biosynthesis.
D A Berges et al.
Journal of medicinal chemistry, 29(1), 89-95 (1986-01-01)
Succinyl-CoA:tetrahydrodipicolinate-N-succinyltransferase is a key enzyme in the biosynthesis of diaminopimelic acid (DAP), a component of the cell wall peptidoglycan of nearly all bacteria. This enzyme converts the cyclic precursor tetrahydrodipicolinic acid (THDPA) to a succinylated acyclic product. L-2-Aminopimelic acid (L-1)
Gabriele Netzel et al.
Toxins, 11(3) (2019-03-22)
In vitro experiments have demonstrated that camel foregut-fluid has the capacity to metabolize indospicine, a natural toxin which causes hepatotoxicosis, but such metabolism is in competition with absorption and outflow of indospicine from the different segments of the digestive system.