Issue 60, 2022

Modular solid-phase synthesis of electrophilic cysteine-selective ethynyl-phosphonamidate peptides

Abstract

We report an efficient method to install electrophilic cysteine-selective ethynyl-phosphonamidates on peptides during Fmoc-based solid phase peptide synthesis (SPPS). By performing Staudinger-phosphonite reactions between different solid supported azido-peptides and varying ethynylphosphonites, we obtained ethynyl-phosphonamidate containing peptidic compounds after acidic deprotection, including an electrophilic cell-penetrating peptide that showed high efficiency as an additive for cellular delivery of proteins.

Graphical abstract: Modular solid-phase synthesis of electrophilic cysteine-selective ethynyl-phosphonamidate peptides

Supplementary files

Article information

Article type
Communication
Submitted
27 avr. 2022
Accepted
22 juin 2022
First published
06 juil. 2022

Chem. Commun., 2022,58, 8388-8391

Modular solid-phase synthesis of electrophilic cysteine-selective ethynyl-phosphonamidate peptides

S. Hansen, J. V. V. Arafiles, P. Ochtrop and C. P. R. Hackenberger, Chem. Commun., 2022, 58, 8388 DOI: 10.1039/D2CC02379B

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