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Solid‐Phase Peptide Macrocyclization and Multifunctionalization via Dipyrrin Construction
Author(s) -
Wu Yue,
Chau HoFai,
Thor Waygen,
Chan Kaitlin Hao Yi,
Ma Xia,
Chan WaiLun,
Long Nicholas J.,
Wong KaLeung
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202108885
Subject(s) - chemistry , peptide , bodipy , combinatorial chemistry , fluorescence , amino acid , ring (chemistry) , aqueous medium , nanotechnology , biochemistry , aqueous solution , organic chemistry , materials science , physics , quantum mechanics
We introduce a new and highly efficient synthetic protocol towards multifunctional fluorescent cyclopeptides by solid‐phase peptide macrocyclization via dipyrrin construction, with full scope of proteinogenic amino acids and different ring sizes. Various bicyclic peptides can be created by dipyrrin‐based crosslinking and double dipyrrin‐ring formation. The embedded dipyrrin can be either transformed to fluorescent BODIPY and then utilized as cancer‐selective targeted protein imaging probe in vitro, or directly employed as a selective metal sensor in aqueous media. This work provides a valuable addition to the peptide macrocyclization toolbox, and a blueprint for the development of multifunctional dipyrrin linkers in cyclopeptides for a wide range of potential bioapplications.