- Synthesis and biological properties of thiazole-analogues of pyochelin, a siderophore of Pseudomonas aeruginosa
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Pyochelin is a siderophore common to all strains of Pseudomonas aeruginosa utilized by this Gram-negative bacterium to acquire iron(III). FptA is the outer membrane transporter responsible of ferric-pyochelin uptake in P. aeruginosa. We describe in this Letter the synthesis and the biological properties ( 55Fe uptake, binding to FptA) of several thiazole analogues of pyochelin. Among them we report in this Letter the two first pyochelin analogues able to bind FptA without promoting any iron uptake in P. aeruginosa.
- No?l, Sabrina,Hoegy, Fran?oise,Rivault, Freddy,Rognan, Didier,Schalk, Isabelle J.,Mislin, Ga?tan L.A.
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p. 132 - 135
(2014/01/17)
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- Bacterial siderophores: Synthesis and biological activities of novel pyochelin analogues
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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
- Zamri,Schalk,Pattus,Abdallah
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p. 1147 - 1150
(2007/10/03)
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- Synthetic studies of thiazoline and thiazolidine-containing natural products. Part 3: Total synthesis and absolute configuration of the siderophore yersiniabactin
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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.
- Ino, Akira,Murabayashi, Akira
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p. 1897 - 1902
(2007/10/03)
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- An improved stereocontrolled synthesis of pyochelin, siderophore of Pseudomonas aeruginosa and Burkholderia cepacia
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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.
- Zamri, Adel,Abdallah, Mohamed A.
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p. 249 - 256
(2007/10/03)
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