Aerobactin synthesis

McDougall S, Neilands JB (1984) Plasmid- and Chromosome-coded Aerobactin Synthesis in Enteric Bacteria Insertion Sequences Flank Operon in Plasmid-mediated Systems. J Bacteriol 159 300... 

Appanna DL, Grund BJ, Szczepan EW, Viswanatha T (1984) Aerobactin synthesis in cell-free system of Aerobacter aerogenes 62-1. Biochim BiophysActa 801 437-443... 

Maurer PJ, Miller Ml (1982) Microbial Iron Chelators Total Synthesis of Aerobactin and its Constituent Amino Acid, if -Acetyl-lf -hydroxylysine. J Am Chem Soc 104 3096... 

PJ Maurer, MJ Miller. Microbial iron chelators total synthesis of aerobactin and its constituent amino acid,N6-acetyl-N6-hydroxylysine. J Am Chem Soc 105 240-245, 1983. 

Fig. 4a. Pathways of hydroxamic acid syntheses of siderophores containing Ns-hydroxyornithine building blocks, a) Starts with e-nitro-L-norvaline. Schemes b) and c) start with ornithine derivatives protected at N5 with CBZ (benzyloxycarbonyl) and Tos (toluenesulfonate), BZL (benzyl), respectively Fig. 4b. Scheme of the synthesis of aerobactin. Protected g-hydroxynorleucine 1 (P = BOC,P = CH3) is transformed into the protected hydroxamic acid 2. Deprotection of the a-NH2 grqup enables alkylation of the o-substituted hydroxamate to give compound 3...

Microbial Iron Chelators Total Synthesis of Aerobactin and Its Constituent Amino Acid, N -Acetyl-N -hydroxylysine. J. Amer. Chem. Soc. 104, 3096 (1982). Kanai, F., K. Isshiki, Y. Umezawa, H. Morishima, H. Naganawa, T. Takita, T. Takeuchi, and H. Umezawa Vanoxonin, a New Inhibitor of Thymidylate Synthetase. II. Structure Determination and Total Synthesis. J. Antibiotics 38, 31 (1985). 

Kiipper FC, CarranoCJ, Kuhn JU, Butler A (2006) Photoreactivity of iron(III)- aerobactin photoproduct structure and iron(lll) coordination. Inorg Chem 45 6028-6033 Guo H, Naser SA, Ghobrial G, Phanstiel O (2002) Synthesis and biological evaluation of new citrate-based siderophores as potential probes for the mechanism iron uptake in mycobacteria. J Med Chem 45 2056-2063... 

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