Molecules, Vol. 24, Pages 2185: A Practical and Total Synthesis of Pasireotide: Synthesis of Cyclic Hexapeptide via a Three-Component Condensation

Molecules, Vol. 24, Pages 2185: A Practical and Total Synthesis of Pasireotide: Synthesis of Cyclic Hexapeptide via a Three-Component Condensation
Molecules doi: 10.3390/molecules24112185
Authors:
Chunying Ma
Miao Chen
Weiming Chu
Jiayi Tao
Delong Kong
Mengmeng Zhang
Wenhua Feng

Pasireotide is a multi-receptor ligand somatostatin analogue approved for medical treatment of Cushing’s disease and acromegaly. The liquid-phase total synthesis of pasireotide-a 18-membered cyclic hexapeptide-was achieved by the 3 + 2 + 1 strategy, and the Pro1-Phe6 peptide bond was selected as the final cyclization position. Two key fragments were simply synthesized using N,O-bis(trimethylsilyl)acetamide/N-hydroxysuccinimide ester (BSA/NHS) as coupling agents, and processes of the two key fragments were simple without any chromatographic purification. The current synthesis method is easily scalable and produces the target peptide with an overall yield of 15%.

Source: Molecules - June 10, 2019 Category: Chemistry Authors: Chunying Ma Miao Chen Weiming Chu Jiayi Tao Delong Kong Mengmeng Zhang Wenhua Feng Tags: Article Source Type: research