Agrochelin

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Category Antibiotics
Catalog number BBF-00391
CAS
Molecular Weight 466.66
Molecular Formula C23H34N2O4S2

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Description

It is produced by the strain of Agrobacterium sp. ALET-304. The IC50 of soil bactericin against P-388 was 0.053 ㎛ol/L, and the IC50 of cell a1-549, HT-29 and MEL 38 was between 0.107-0.268 ㎛ol/L.

Specification

Synonyms (3S)-3-hydroxy-3-{(2S,4R)-2-[(4R)-2-(2-hydroxy-6-pentylphenyl)-4,5-dihydro-1,3-thiazol-4-yl]-3-methyl-1,3-thiazolidin-4-yl}-2,2-dimethylpropanoic acid; CHEBI:65375; Q27133819
IUPAC Name (3S)-3-hydroxy-3-[(2S,4R)-2-[(4R)-2-(2-hydroxy-6-pentylphenyl)-4,5-dihydro-1,3-thiazol-4-yl]-3-methyl-1,3-thiazolidin-4-yl]-2,2-dimethylpropanoic acid
Canonical SMILES CCCCCC1=C(C(=CC=C1)O)C2=NC(CS2)C3N(C(CS3)C(C(C)(C)C(=O)O)O)C
InChI InChI=1S/C23H34N2O4S2/c1-5-6-7-9-14-10-8-11-17(26)18(14)20-24-15(12-30-20)21-25(4)16(13-31-21)19(27)23(2,3)22(28)29/h8,10-11,15-16,19,21,26-27H,5-7,9,12-13H2,1-4H3,(H,28,29)/t15-,16+,19-,21+/m1/s1
InChI Key QZBCDLLHQSDFIG-ZEVBXJOLSA-N

Properties

Appearance Pale Yellow Oily Matter
Solubility Soluble in Chloroform, Methanol

Reference Reading

1. Agrochelin, a new cytotoxic antibiotic from a marine Agrobacterium. Taxonomy, fermentation, isolation, physico-chemical properties and biological activity
C Acebal, L M Cañedo, J L Puentes, J P Baz, F Romero, F de la Calle, M D Grávalos, P Rodriguez J Antibiot (Tokyo). 1999 Nov;52(11):983-7. doi: 10.7164/antibiotics.52.983.
Agrochelin, a new alkaloid cytotoxic substance, was produced by the fermentation of Agrobacterium sp. The compound was obtained from the bacterial cells by solvent extraction and purified by silica gel chromatography. Agrochelin (1) and its acetyl derivative (2) exhibited cytotoxic activity.
2. Genomics-inspired discovery of massiliachelin, an agrochelin epimer from Massilia sp. NR 4-1
Jan Diettrich, Hirokazu Kage, Markus Nett Beilstein J Org Chem. 2019 Jun 13;15:1298-1303. doi: 10.3762/bjoc.15.128. eCollection 2019.
A putative siderophore locus was detected in the genome of the violacein-producing bacterium Massilia sp. NR 4-1 and predicted to direct the biosynthesis of a molecule that is structurally related to the thiazoline-containing siderophore micacocidin. In order to track this compound, we analyzed the metabolic profiles of Massilia cultures grown under different iron concentrations. A compound which was found to be predominantly produced under iron deficiency was subsequently isolated. Its structural characterization by spectroscopic and bioinformatic analyses revealed a previously not known diastereomer of the cytotoxic alkaloid agrochelin. The structure of this natural product, which was named massiliachelin, corresponds to the assembly line encoded by the identified siderophore locus.

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