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Published on: January 13, 2017
Total Synthesis, Antibacterial Activity, and Structural Analysis of Atratumycin and Its Analogues
Yuya Sawayama1, Rintaro Kaguchi1, Motoko Shinohara2
1Faculty of Pharmaceutical Sciences, Hokkaido University, Kita-12, Nishi-6, Kita-ku, Sapporo 060-0812, Japan.
None:
Solid-phase total synthesis of atratumycin (1) and its analogues is described. The linear depsipeptide was synthesized by the standard Fmoc solid-phase peptide synthesis, on-resin esterification, and epimerization-free macrolactamization. A structure-activity relationship study of 1 led to the identification of the amino acid residue that preserves its antituberculosis activity. Conformational analyses of 1 and its analogues revealed that the solution structure of 1 closely resembles the crystal structure of 1, suggesting the structural rigidity of its unique conformation.
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