A novel strategy for the solid-phase synthesis of cyclic lipodepsipeptides |
| |
Authors: | Stawikowski Maciej Cudic Predrag |
| |
Institution: | Department of Chemistry and Biochemistry, Charles E. Schmidt College of Science, Florida Atlantic University, 777 Glades Road, Boca Raton, FL 33431, USA |
| |
Abstract: | A rapid and efficient Fmoc solid-phase synthesis of cyclic lipodepsipeptide analogue 1 to antibiotic fusaricidin A is described. Our synthetic approach includes resin attachment of the first amino acid via side chain, successful use of combination of four quasi-orthogonal removable protecting groups, stepwise solid-phase synthesis of linear peptide analogue, lipid tail attachment followed by depsipeptide bond formation and on-resin head-to-tail cyclization. Undesired O→N acyl shift, which may occur during Fmoc removal, was successfully avoided by the incorporation of the lipid tail into the linear peptide precursor prior to on-resin depsipeptide bond formation and the ring closure. |
| |
Keywords: | Cyclic lipodepsipeptides Fmoc solid-phase synthesis Fusaricidin A O&rarr N Acyl shift |
本文献已被 ScienceDirect PubMed 等数据库收录! |
|