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A1880

Sigma-Aldrich

(±)-2-Aminopimelic acid

≥99%

Synonym(s):

(±)-2-Aminoheptanedioic acid

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About This Item

Empirical Formula (Hill Notation):
C7H13NO4
CAS Number:
627-76-9
Molecular Weight:
175.18
Beilstein/REAXYS Number:
1722015
EC Number:
211-011-7
MDL number:
MFCD00053314
UNSPSC Code:
12352200
PubChem Substance ID:
24890596

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

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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.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H319,H335

Hazard Classifications

Eye Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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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)
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
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.
Jie Zhao et al.
Biomedical chromatography : BMC, 32(10), e4299-e4299 (2018-05-26)
Triptolide, a major active constitute of Tripterygium wilfordii Hook. F, is prescribed for the treatment of autoimmune diseases in China. One of its most severe adverse effects observed in the clinical use is hepatotoxicity, but the mechanism is still unknown.
Hui-Chang Bi et al.
Carcinogenesis, 35(10), 2264-2272 (2014-08-15)
The cell metabolome comprises abundant information that may be predictive of cell functions in response to epigenetic or genetic changes at different stages of cell proliferation and metastasis. An unbiased ultra-performance liquid chromatography-mass spectrometry-based metabolomics study revealed a significantly altered

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