5 years ago

Reversible and Versatile On-Tether Modification of Chiral-Center-Induced Helical Peptides

Reversible and Versatile On-Tether Modification of Chiral-Center-Induced Helical Peptides
Zigang Li, Chengjie Sun, Kuan Hu
Modification of the cross-linker of constrained peptides has recently received considerable attention. Here, we present a versatile approach to modifing the cross-linking tether of chiral-center-induced helical (CIH) peptides via the S-alkylation reaction. The alkylation process displayed high conversion efficiency, selectivity, and substrate tolerance. Notably, although on-tether S-alkylation could lead to a pair of peptide epimers, the major alkylated product retained the helical structure of its helical precursor peptide. This S-alkylation was readily reversible under reductive conditions, which provides a simple method for traceless modification. In addition to expanding the chemical space of CIH peptides, this strategy is the first on-tether modification platform with known retention of the peptides’ original helicity.

Publisher URL: http://dx.doi.org/10.1021/acs.bioconjchem.7b00321

DOI: 10.1021/acs.bioconjchem.7b00321

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