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 এপ্রিল 2022
Accepted
22 জুন 2022
First published
06 জুলাই 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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements