Peptide Macrocyclization Assisted by Traceless Turn Inducers Derived from Ugi Peptide Ligation with Cleavable and Resin-Linked Amines | Zendy

Alfredo R. Puentes | Zendy; Micjel Chávez Morejón | Zendy; Daniel G. Rivera | Zendy; Ludger A. Wessjohann | Zendy

Open Access

Peptide Macrocyclization Assisted by Traceless Turn Inducers Derived from Ugi Peptide Ligation with Cleavable and Resin-Linked Amines

Author(s) -

Alfredo R. Puentes,

Micjel Chávez Morejón,

Daniel G. Rivera,

Ludger A. Wessjohann

Publication year - 2017

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.7b01761

Subject(s) - chemistry , linker , amide , peptide , combinatorial chemistry , ugi reaction , cleavage (geology) , turn (biochemistry) , ligation , oligopeptide , cyclic peptide , solid phase synthesis , carboxylic acid , stereochemistry , organic chemistry , biochemistry , isocyanide , geotechnical engineering , microbiology and biotechnology , fracture (geology) , computer science , engineering , biology , operating system

A multicomponent approach enabling the installation of turn-inducing moieties that facilitate the macrocyclization of short and medium-size oligopeptides is described. The strategy comprises the Ugi ligation of peptide carboxylic acids and isocyanopeptides in the presence of aldehydes and acid or photolabile amines followed by cyclization and cleavage of the backbone N-substituents to render canonical cyclopeptides. Implementing the approach on solid phase with the use of Rink amide resins led to a new class of backbone amide linker strategy.

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