Aladapcin

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Aladapcin
Category Others
Catalog number BBF-00398
CAS 114540-27-1
Molecular Weight 331.37
Molecular Formula C13H25N5O5
Purity 95%

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Description

It is produced by the strain of Nocardia sp. SANK 60484. Alanine in 1-100 ㎍/kg can enhance the resistance of mice against experimental E. coli infection.

Specification

Synonyms SCHEMBL4061749; DTXSID90921412; N-{2-[(2,6-Diamino-1,7-dihydroxy-7-iminoheptylidene)amino]-1-hydroxypropylidene}alanine
IUPAC Name 2-[2-[(2,6,7-triamino-7-oxoheptanoyl)amino]propanoylamino]propanoic acid
Canonical SMILES CC(C(=O)NC(C)C(=O)O)NC(=O)C(CCCC(C(=O)N)N)N
InChI InChI=1S/C13H25N5O5/c1-6(11(20)18-7(2)13(22)23)17-12(21)9(15)5-3-4-8(14)10(16)19/h6-9H,3-5,14-15H2,1-2H3,(H2,16,19)(H,17,21)(H,18,20)(H,22,23)
InChI Key JPUODCQOVNYKMH-UHFFFAOYSA-N

Properties

Appearance White Powder
Boiling Point 772.6 °C at 760 mmHg
Density 1.278 g/cm3
Solubility Soluble in Methanol, Water; Insoluble in Chloroform, Acetone

Reference Reading

1. Aladapcin, a new microbial metabolite that enhances host resistance against bacterial infection. Production, isolation, physico-chemical properties and biological activities
A Shiraishi, M Nakajima, T Katayama, T Matsuda, T Niwa, T Okazaki, Y Takamatsu, H Nagaki, T Kinoshita, T Takatsu, et al. J Antibiot (Tokyo). 1990 Jun;43(6):634-8. doi: 10.7164/antibiotics.43.634.
We have constructed a new screening system for detecting microbial products that enhance host resistance against bacterial infection. It was found that a new compound with such activity is produced by a soil isolate classified as Nocardia sp. SANK 60484. The compound was isolated from the culture filtrate of the organism and named aladapcin after its amino acid composition. Aladapcin was obtained as an amphoteric white amorphous powder with the molecular formula, C13H25N5O5. It consists of 2 mol of D-alanine and 1 mol of meso-diaminopimelic acid. From the analysis of IR, 1H NMR and FAB-MS spectra, the structure was assigned to be a tripeptide. Aladapcin enhanced host resistance against an experimental Escherichia coli infection in mice at doses ranging between 1 and 100 micrograms/kg.

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