Regioselective and Efficient Synthesis of Nonsymmetric Cyclic Peptides via a Stapling Reaction of 2‐Acetyl‐thiophene‐3‐carboxaldehyde with Primary Amine and Thiol DOI
Tianyu Bo, Jia‐Wei Wang,

Ruotong Liang

и другие.

Chemistry - An Asian Journal, Год журнала: 2025, Номер unknown

Опубликована: Май 6, 2025

Abstract In this work, 13 nonsymmetric cyclic peptides with a thieno[2,3‐ c ]pyrrole bridge were efficiently and regioselectively synthesized by stapling reaction of the primary amine (from lysine (Lys) side chain peptide N ‐terminus), thiol cysteine (Cys) chain), 2‐acetyl‐thiophene‐3‐carboxaldehyde (ATA). A single regioisomeric staple was formed, generating ]pyrrole‐bridged peptide. The can be carried out in various solvents. Moreover, obtained stable PBS solution. Furthermore, three bicyclic containing both an acetone‐like via two strategies: (1) symmetric 1,3‐dichloroacetone (DCA) Cys residues, (2) ATA Lys residues. Satisfied yields achieved. positions bridges determined synthetic accessiblity peptides. Certainly, wide variety designed, thus entrenching methodologies cyclization. strategy is applied conveniently to synthesis large structural diversity.

Язык: Английский

Regioselective and Efficient Synthesis of Nonsymmetric Cyclic Peptides via a Stapling Reaction of 2‐Acetyl‐thiophene‐3‐carboxaldehyde with Primary Amine and Thiol DOI
Tianyu Bo, Jia‐Wei Wang,

Ruotong Liang

и другие.

Chemistry - An Asian Journal, Год журнала: 2025, Номер unknown

Опубликована: Май 6, 2025

Abstract In this work, 13 nonsymmetric cyclic peptides with a thieno[2,3‐ c ]pyrrole bridge were efficiently and regioselectively synthesized by stapling reaction of the primary amine (from lysine (Lys) side chain peptide N ‐terminus), thiol cysteine (Cys) chain), 2‐acetyl‐thiophene‐3‐carboxaldehyde (ATA). A single regioisomeric staple was formed, generating ]pyrrole‐bridged peptide. The can be carried out in various solvents. Moreover, obtained stable PBS solution. Furthermore, three bicyclic containing both an acetone‐like via two strategies: (1) symmetric 1,3‐dichloroacetone (DCA) Cys residues, (2) ATA Lys residues. Satisfied yields achieved. positions bridges determined synthetic accessiblity peptides. Certainly, wide variety designed, thus entrenching methodologies cyclization. strategy is applied conveniently to synthesis large structural diversity.

Язык: Английский

Процитировано

0