338461-20-4Relevant academic research and scientific papers
Convergent Total Synthesis of the Siderophore Piscibactin as Its Ga3+Complex
De La Fuente, M. Carmen,Jiménez, Carlos,Rodríguez, Jaime,Segade, Yuri,Valderrama, Katherine
supporting information, p. 340 - 345 (2021/01/13)
The siderophore piscibactin is a key virulence factor involved in the iron uptake of pathogenic bacteria Photobacterium damselae subsp. piscicida and Vibrio anguillarum, responsible for the fish diseases photobacterioisis (pasteurellosis) and vibriosis, respectively. A convergent total synthesis of its Ga3+ complex using l-/d-cysteine as chiral agents and Meldrum's acid is described. A Staudinger reduction/Aza-Wittig process in the synthesis of the acid-sensitive β-hydroxy-2,4-disubstituted thiazoline moiety and the convenient protecting groups was a key step in this synthesis.
Biologically Inspired Total Synthesis of Ulbactin F, an Iron-Binding Natural Product
Shapiro, Justin A.,Morrison, Kelly R.,Chodisetty, Shreya S.,Musaev, Djamaladdin G.,Wuest, William M.
supporting information, p. 5922 - 5926 (2018/09/21)
Natural products from environmental microbiomes provide exquisite templates for elucidating biological activity in the search for new drugs. A recently discovered marine Brevibacillus sp. metabolite, ulbactin F, was found to inhibit tumor cell migration a
A Short stereoselective synthesis of prepiscibactin using a SmI2-mediated reformatsky reaction and zn2+-induced asymmetric thiazolidine formation
Segade, Yuri,Montaos, Marcos A.,Rodrguez, Jaime,Jimnez, Carlos
supporting information, p. 5820 - 5823 (2015/02/19)
Prepiscibactin (1) is a possible intermediate in the biosynthesis of piscibactin, the siderophore responsible for the iron uptake of the bacterium Photobacterium damselae subsp. piscicida, the aethiological agent of fish pasteurellosis. Compound 1 was syn
Synthesis of fluorescent probes based on the pyochelin siderophore scaffold
Noel, Sabrina,Guillon, Laurent,Schalk, Isabelle J.,Mislin, Gaetan L. A.
supporting information; experimental part, p. 844 - 847 (2011/04/27)
Pyochelin is a siderophore common to several pathogenic bacterial strains. Two conjugates, 1 and 2, between the NBD (4-nitro-benzo[1,2,5]oxadiazole) fluorophore and an N3′′-functionalized pyochelin were synthesized. These fluorescent probes unexpectedly increased their fluorescence in an aqueous medium in the presence of iron(III) and were transported into bacterial cells.(Figure Presented)
Synthetic studies of thiazoline and thiazolidine-containing natural products. Part 3: Total synthesis and absolute configuration of the siderophore yersiniabactin
Ino, Akira,Murabayashi, Akira
, p. 1897 - 1902 (2007/10/03)
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.
