69772-54-9

Usage

Uses

Used in Pharmaceutical Applications:
Pyochelin is used as an iron-chelating growth promoter for Pseudomonas aeruginosa, facilitating the bacteria's ability to acquire iron from the environment, which is vital for their growth and survival.
Used in Research and Development:
Pyochelin is used as a research tool in the study of bacterial iron acquisition mechanisms, siderophore production, and the development of novel antimicrobial strategies targeting bacterial iron uptake systems.
Used in Microbiology:
Pyochelin is utilized in microbiological research to understand the role of siderophores in bacterial pathogenesis and their potential as targets for new therapeutic interventions against bacterial infections.
Used in Chemical Synthesis:
Pyochelin serves as a starting material or a structural template for the synthesis of novel siderophore-based compounds with potential applications in various fields, including medicine, agriculture, and environmental science.

InChI:InChI=1/C14H16N2O3S2/c1-16-10(14(18)19)7-21-13(16)9-6-20-12(15-9)8-4-2-3-5-11(8)17/h2-5,9-10,13,15H,6-7H2,1H3,(H,18,19)/b12-8+/t9-,10+,13?/m1/s1

Upstream product

• 14344-46-8 (R)-N-methylcysteine hydrochloride 
• 118446-23-4 2-(2-Hydroxyphenyl)-2-thiazoline-4-carboxaldehyde 
• 4026-48-6 N-methyl-L-cysteine 
• 163526-41-8 2'-(2-hydroxyphenyl)-2'-thiazoline-4'-carboxaldehyde 
• 21615-34-9 2-Methoxybenzoyl chloride 
• 611-20-1 salicylonitrile 
• 338461-21-5 (4S)-2-[2-(tert-butyldiphenylsilyloxy)phenyl]-4,5-dihydrothiazole-4-carboxylic acid N-methoxy-N-methylamide 
• 338461-17-9 (2R)-2-tert-butoxycarbonylamino-N-methoxy-3-(2-methoxybenzyloxy)-N-methylpropionamide 
• 338461-19-1 (2R)-3-hydroxy-2-(2-hydroxybenzoylamino)-N-methoxy-N-methylpropionamide 
• 338461-14-6 (2R)-3-hydroxy-2-(2-hydroxythiobenzoylamino)-N-methoxy-N-methylpropionamide 
• 338461-18-0 (2R)-3-hydroxy-N-methoxy-2-(2-methoxybenzoylamino)-N-methylpropionamide 
• 338461-20-4 (4S)-2-(2-hydroxyphenyl)-4,5-dihydrothiazole-4-carboxylic acid N-methoxy-N-methylamide 
• 262419-95-4 2'-(2-t-butyldiphenylsilyloxyphenyl)-2'-thiazoline-4'-carboxaldehyde 
• 262419-96-5 (4R)-2-(2-hydroxyphenyl)-4,5-dihydrothiazole-4-carboxylic acid N-methoxy-N-methylamide 

Relevant academic research and scientific papers

Bacterial siderophores: Synthesis and biological activities of novel pyochelin analogues

The synthesis and biological activities of four pyochelin analogues substituted in different parts of the molecule are reported: 5-NHBoc-pyochelin, 3″N-Boc-pyochelin, 3″-nor-NH-pyochelin and neopyochelin II, the enantiomer of natural pyochelin. All these

Synthetic studies of thiazoline and thiazolidine-containing natural products. Part 3: Total synthesis and absolute configuration of the siderophore yersiniabactin

Total synthesis of yersiniabactin, a siderophore from cultures of the bacterium Yersinia enterocolitica, was accomplished. Chirality at the readily racemizable C-9 carbon was preserved during cyclization of β-hydroxythioamide by means of Burgess reagent leading to thiazoline. Based on its synthesis, the absolute configuration of natural yersiniabactin has been determined as 9R, 10RS, 12R, 13S and 19S.

An improved stereocontrolled synthesis of pyochelin, siderophore of Pseudomonas aeruginosa and Burkholderia cepacia

A considerably improved stereocontrolled synthesis of pyochelin, a hydroxyphenylthiazolinylthiazolidine type of siderophore common to most strains of Pseudomonas aeruginosa and Burkholderia cepacia is described. 2'- (2-Hydroxyphenyl)-2'-thiazoline-4'-carboxaldehyde, a key molecule involved in this synthesis has been prepared by reduction of 2'-(2-hydroxyphenyl)-2'- thiazoline-4'-(N-methoxy,N-methyl) carboxamide with lithium aluminium hydride. The aldehyde was further coupled with (R)-N-methylcysteine to yield pyochelin. Under the conditions reported, epimerization at the C-4' center was considerably diminished.

Stereochemical assignment of the pyochelins

The synthesis of pyochelin has been much improved but gives four stereoisomers. The stereochemistry of the two naturally occurring pyochelins I and II has been assigned, based on (1) the similarity of the NMR spectra of pyochelin I methyl ester to those f