32393-54-7

Upstream product

• 7733-29-1 Z-Orn(Boc)-OH 
• 13650-49-2 N^δ-(tert-butoxycarbonyl)-L-ornithine 

Downstream Products

• 250215-13-5 (S)-2-{(S)-2-[(S)-2-(benzyloxycarbonylamino)-5-(tertbutoxycarbonylamino)valerylamino]-5-(tert-butoxycarbonylamino)valerylamino}-5-(tert-butoxycarbonylamino)valeric acid 
• 250215-17-9 (S)-2-((S)-2-((S)-2-Benzyloxycarbonylamino-5-{[1-phenyl-meth-(E)-ylidene]-amino}-pentanoylamino)-5-{[1-phenyl-meth-(E)-ylidene]-amino}-pentanoylamino)-5-{[1-phenyl-meth-(E)-ylidene]-amino}-pentanoic acid 

Relevant academic research and scientific papers

Theranostic Gallium Siderophore Ciprofloxacin Conjugate with Broad Spectrum Antibiotic Potency

Pathogenic bacteria scavenge ferric iron from the host for survival and proliferation using small-molecular chelators, siderophores. Here, we introduce and assess the gallium(III) complex of ciprofloxacin-functionalized desferrichrome (D2) as a potential therapeutic for bacterial infection using an in vitro assay and radiochemical, tracer-based approach. Ga-D2 exhibits a minimum inhibitory concentration of 0.23 μM in Escherichia coli, in line with the parent fluoroquinolone antibiotic. Competitive and mutant strain assays show that Ga-D2 relies on FhuA-mediated transport for internalization. Ga-D2 is potent against Pseudomonas aeruginosa (3.8 μM), Staphylococcus aureus (0.94 μM), and Klebsiella pneumoniae (12.5 μM), while Fe-D2 is inactive in these strains. Radiochemical experiments with E. coli reveal that 67Ga-D2 is taken up more efficiently than 67Ga-citrate. In naive mice, 67Ga-D2 clears renally and is excreted 13% intact in the urine. These pharmacokinetic and bacterial growth inhibitory properties qualify Ga-D2 for future investigations as a diagnosis and treatment tool for infection.

Practical synthesis of hydroxamate-derived siderophore components by an indirect oxidation method and syntheses of a DIG-siderophore conjugate and a biotin-siderophore conjugate

A practical large-scale synthesis of hydroxamate-derived siderophore components (30 and 40) that utilizes an efficient indirect oxidation method is described and applied to the syntheses of nonradioactive labeled siderophores. Oxidation of imines derived from L-ornithine (17) and its tripeptide (19) afforded oxaziridines that were isomerized to stable nitrones (16 and 18). Acid-catalyzed hydrolysis of nitrones provided hydroxylamines that were converted to the desired hydroxamic acids (30 and 40) suitable for constructing siderophore-drug conjugates (2). The entire synthetic sequence required no chromatographic separation. DIG- and biotin-labeled ferrichrome analogues designed to detect and isolate ferrichrome receptors in various microbes were also synthesized.