Synthesis of Novel Citrate-Based Siderophores and Siderophore-β-Lactam Conjugates. Iron Transport-Mediated Drug Delivery Systems

Article abstract of DOI:10.1021/jo00079a007

The synthesis of analogs of arthrobactin (5), a microbial iron chelator, and its imide 8 are described.The differentially protected citric acid residue 31 served as the key intermediate in making conjugates having a generalized structure 14 with two representative carbacephalosporin units, 15 and 16.Both conjugates, 49 and 51, showed antibiotic activity, while conjugate 51 obtained from β-lactam 16 bearing a phenylglycyl side chain was shown to be more effective.