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A Practical and Total Synthesis of Pasireotide: Synthesis of Cyclic Hexapeptide via a Three-Component Condensation

Department of New Drug Research and Development, Institute of Materia Medical, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050, China
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Molecules 2019, 24(11), 2185; https://doi.org/10.3390/molecules24112185
Received: 29 April 2019 / Revised: 29 May 2019 / Accepted: 4 June 2019 / Published: 11 June 2019
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%. View Full-Text
Keywords: pasireotide; liquid-phase; synthesis; BSA/NHS; cyclic hexapeptide pasireotide; liquid-phase; synthesis; BSA/NHS; cyclic hexapeptide
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MDPI and ACS Style

Ma, C.; Chen, M.; Chu, W.; Tao, J.; Kong, D.; Zhang, M.; Feng, W. A Practical and Total Synthesis of Pasireotide: Synthesis of Cyclic Hexapeptide via a Three-Component Condensation. Molecules 2019, 24, 2185.

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