Synthesis of Constrained Tetracyclic Peptides by Consecutive CEPS, CLIPS, and Oxime Ligation | Zendy

Dieuwertje E. Streefkerk | Zendy; Marcel Schmidt | Zendy; Hans Ippel | Zendy; Tilman M. Hackeng | Zendy; Timo Nuijens | Zendy; Peter Timmerman | Zendy; Jan H. van Maarseveen | Zendy

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Synthesis of Constrained Tetracyclic Peptides by Consecutive CEPS, CLIPS, and Oxime Ligation

Author(s) -

Dieuwertje E. Streefkerk,

Marcel Schmidt,

Hans Ippel,

Tilman M. Hackeng,

Timo Nuijens,

Peter Timmerman,

Jan H. van Maarseveen

Publication year - 2019

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.9b00378

Subject(s) - chemistry , oxime , combinatorial chemistry , alkylation , chemical ligation , peptide , native chemical ligation , scaffold , small molecule , amino acid , molecule , stereochemistry , enzyme , organic chemistry , biochemistry , catalysis , cysteine , medicine , biomedical engineering

In Nature, multicyclic peptides constitute a versatile molecule class with various biological functions. For their pharmaceutical exploitation, chemical methodologies that enable selective consecutive macrocyclizations are required. We disclose a combination of enzymatic macrocyclization, CLIPS alkylation, and oxime ligation to prepare tetracyclic peptides. Five new small molecular scaffolds and differently sized model peptides featuring noncanonical amino acids were synthesized. Enzymatic macrocyclization, followed by one-pot scaffold-assisted cyclizations, yielded 21 tetracyclic peptides in a facile and robust manner.

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