Solid Phase Library Synthesis of Cyclic Depsipeptides: Aurilide and Aurilide Analogues
Citations Over TimeTop 20% of 2003 papers
Abstract
A solid-phase combinatorial synthesis approach toward the cyclic depsipeptide aurilide (1) and related analogues is described. The peptide moiety 2 was assembled on trityl linker-functionalized SynPhase Crowns using an Fmoc strategy. Optimization of the tetrapeptide assembly 5 was carried out using parallel multiple synthesis and LC/MS analysis. The aliphatic moiety 3a was coupled with the solid-supported 2 using DIC/HOBt. Following deprotection and cleavage of linear precursor 26, macrocyclization was achieved under high dilution conditions. Removal of the methylthiomethyl protecting group provided aurilide (1) in 11% overall yield. Synthesis of a combinatorial library of aurilide derivatives 4 was accomplished with a similar protocol using the TranSort technique.
Related Papers
- → N-Methylsansalvamide A Peptide Analogues. Potent New Antitumor Agents(2005)83 cited
- → Identification of Novel Low Molecular Weight CXCR4 Antagonists by Structural Tuning of Cyclic Tetrapeptide Scaffolds(2005)83 cited
- → Cyclic tetrapeptides via the ring contraction strategy: chemical techniques useful for their identification(2008)38 cited
- → Synthesis of L-cyclic tetrapeptides by backbone amide activation CyClick strategy(2022)11 cited
- → Exploring Solution-Phase Cyclization and Sulfamyl Safety-Catch Resin Strategies for the Total Synthesis of the Marine Antimicrobial Cyclic Tetrapeptide Cyclo(GSPE)(2012)4 cited