250215-21-5

Basic information

• Product Name: N²-Z-N⁵-acetyl-N⁵-O-acetyl-L-ornithyl-N⁵-acetyl-N⁵-O-acetyl-L-ornithyl-N⁵-acetyl-N⁵-O-acetyl-L-ornithine
• Synonyms: N²-Z-N⁵-acetyl-N⁵-O-acetyl-L-ornithyl-N⁵-acetyl-N⁵-O-acetyl-L-ornithyl-N⁵-acetyl-N⁵-O-acetyl-L-ornithine
• CAS NO: 250215-21-5
• Molecular Weight: 794.813
• Mol File: 250215-21-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: N²-Z-N⁵-acetyl-N⁵-O-acetyl-L-ornithyl-N⁵-acetyl-N⁵-O-acetyl-L-ornithyl-N⁵-acetyl-N⁵-O-acetyl-L-ornithine(CAS DataBase Reference)
• NIST Chemistry Reference: N²-Z-N⁵-acetyl-N⁵-O-acetyl-L-ornithyl-N⁵-acetyl-N⁵-O-acetyl-L-ornithyl-N⁵-acetyl-N⁵-O-acetyl-L-ornithine(250215-21-5)
• EPA Substance Registry System: N²-Z-N⁵-acetyl-N⁵-O-acetyl-L-ornithyl-N⁵-acetyl-N⁵-O-acetyl-L-ornithyl-N⁵-acetyl-N⁵-O-acetyl-L-ornithine(250215-21-5)

Safety Data

• Hazardous Substances Data: 250215-21-5(Hazardous Substances Data)

Upstream product

• 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 
• 108-24-7 acetic anhydride 
• 250215-13-5 (S)-2-{(S)-2-[(S)-2-(benzyloxycarbonylamino)-5-(tertbutoxycarbonylamino)valerylamino]-5-(tert-butoxycarbonylamino)valerylamino}-5-(tert-butoxycarbonylamino)valeric acid 
• 7733-29-1 Z-Orn(Boc)-OH 
• 13650-49-2 N^δ-(tert-butoxycarbonyl)-L-ornithine 

Relevant articles and documents

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.