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Fmoc-L-Orn(Ac,OBz)-OH
Chemical name: N-alpha-(9-Fluorenylmethyloxycarbonyl)-N-delta-acetyl-N-delta-benzoyloxy-L-ornithine // Synonyms: (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-5-(N-(benzoyloxy)acetamido)pentanoic acid, Fmoc-Orn(Ac,Obz)-OH
- Product code:FAA4220
- CAS No.:1684432-88-9
- Formula:C29H28N2O7
- Storage temperature:-20°C
- Molecular weight:516.55 g/mol
from $812.50
description
The hydroxamate-ornithine derivative N-delta-hydroxy-N-delta-acetyl-ornithine is a bidentate ligand that is found in many siderophores, a Fe(III)-binding class of biomolecules that can be employed as siderophore-drug-conjugates (“Trojan Horse Strategy”). The N-alpha-Fmoc-N-delta-acetyl-N-delta-benzyloxycarbonyl-L-ornithine building block is suitable for SPPS. Moreover, the N-delta-group can be deprotected on-resin to liberate the native metal-ion-binding N-delta-hydroxy-N-delta-acetyl-motif. Conditions for on-resin N-delta-deprotection: 1 M LiOH in THF/MeOH (1:1)
references
Enterobactin-Mediated Delivery of ß-Lactam Antibiotics Enhances Antibacterial Activity against Pathogenic Escherichia coli; T. Zheng and E. M. Nolan; Journal of the American Chemical Society 2014; 136: 9677-9691. doi:10.1021/ja503911p Siderophore-Mediated Cargo Delivery to the Cytoplasm of Escherichia coli and Pseudomonas aeruginosa: Syntheses of Monofunctionalized Enterobactin Scaffolds and Evaluation of Enterobactin-Cargo Conjugate Uptake; T. Zheng, J. L. Bullock and E. M. Nolan; Journal of the American Chemical Society 2012; 134: 18388-18400 doi:10.1021/ja3077268 Exploiting bacterial iron acquisition: siderophore conjugates; C. Ji, R. E. Juarez-Hernandez and M. J. Miller; Future medicinal chemistry 2012; 4: 297-313. doi:10.4155/fmc.11.191
Design and synthesis of a siderophore conjugate as a potent PSMA inhibitor and potential diagnostic agent for prostate cancer; P. Ding, P. Helquist and M. J. Miller; Bioorganic & Medicinal Chemistry 2008; 16: 1648-1657. doi:http://dx.doi.org/10.1016/j.bmc.2007.11.030
Design and synthesis of a novel protected mixed ligand siderophore; P. Ding, C. E. Schous and M. J. Miller; Tetrahedron letters 2008; 49: 2306-2310. doi:10.1016/j.tetlet.2008.02.007
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