Synthesis of Cycle-Tail Peptides in the Pseudacyclins A-E Family

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Voyer’s team reported the first total synthesis of the cycle-tail peptides known as pseudacyclins A-E with high overall yields. The strategy was based on the use of orthogonally protected ornithine that yielded protected-cyclic peptides that were later hydrogenolyzed to give the exocyclic amines. The hydrogenolysis step of these types of syntheses is usually purified by HPLC, and the purification is long, tedious, and gives poor yields. Voyer’s team developed a powerful normal-phase method for rapid separation of the monomers from the dimers using SiliaSep PREMIUM Spherical Flash Cartridges obtaining yields from 52 to 56 % with a purity of 98 to 99 %. The chromatographic conditions are reported below.

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