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Phosphonodithioester-amine coupling in water: a fast reaction to modify the surface of liposomes†
Montassar Khalil,Dany Jeanne Dit Fouque,Mathieu Berchel,Aurore Fraix,Aurélien Dupont,Salvatore Sortino,Antony Memboeuf,Paul-Alain Jaffrès
Organic & Biomolecular Chemistry Pub Date : 06/28/2021 00:00:00 , DOI:10.1039/D1OB01078F
Abstract

The incorporation of lipophilic phosphonodithioesters in phospholipid formulations generates clickable liposomes that react with amines. The kinetics of this metal free phosphonodithioester-amine coupling (PAC) on liposomes in water is reported and can be classified as a fast reaction with a second order rate constant of k ≈ 8 × 102 M−1 s−1. The PAC reaction represents a versatile strategy to functionalize liposomes.

Graphical abstract: Phosphonodithioester-amine coupling in water: a fast reaction to modify the surface of liposomes
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