Cationic oligonucleotide derivatives and conjugates: A favorable approach for enhanced DNA and RNA targeting oligonucleotides

• Mathias B. Danielsen and
• Jesper Wengel

Beilstein J. Org. Chem. 2021, 17, 1828–1848, doi:10.3762/bjoc.17.125

• ]. Notably, optimization of the therapeutic window of ASOs is closely related to improved delivery, and a variety of chemical strategies have been investigated in this context, such as ASO–lipid conjugates for improved endosomal escape [21], ASO–triantennary N-acetylgalactosamine (GalNAc) conjugates for

Enhanced target cell specificity and uptake of lipid nanoparticles using RNA aptamers and peptides

• Roslyn M. Ray,
• Anders Højgaard Hansen,
• Maria Taskova,
• Bernhard Jandl,
• Jonas Hansen,
• Citra Soemardy,
• Kevin V. Morris and
• Kira Astakhova

Beilstein J. Org. Chem. 2021, 17, 891–907, doi:10.3762/bjoc.17.75

• -HAIYPRH-NH2 Tat: H-YGRKKRRQRRR-NH2 Modified Tat: dipalmitoyl-Dap-YGRKKRRQRRR-NH2 Peptide conjugation with a lipid reagent The peptides were N-terminally modified on solid support by coupling of Fmoc-Dap(Fmoc)-OH, followed by the coupling of palmitic acid to afford the complete peptide–lipid conjugates

• . Coupling of Fmoc-Dap(Fmoc)-OH and Fmoc deprotection were carried out as described above. To ensure the complete lipidation of the two free amines of Dap, 8 equiv of palmitic acid, 8 equiv of HATU, and 12 equiv of DIPEA in DMF were used. Cleavage of the peptide–lipid conjugates from the solid support and

Synthesis and physicochemical evaluation of fluorinated lipopeptide precursors of ligands for microbubble targeting

• Masayori Hagimori,
• Estefanía E. Mendoza-Ortega and
• Marie Pierre Krafft

Beilstein J. Org. Chem. 2021, 17, 511–518, doi:10.3762/bjoc.17.45

• particular cell surface receptor [7][9][10][11][12][13][14]. To this aim, ligand–lipid conjugates have been developed in research and preclinical development for liposome targeting for decades. In particular, peptide ligands offer significant advantages, including efficient synthesis routes, versatility, and

• safety [15][16][17]. Various effective receptor-binding peptides have been identified by the phage display technology [18]. The peptides can be readily prepared through solid-phase peptide synthesis (SPPS), a highly reproducible method with minimal side reactions. Many peptide–lipid conjugates

• fluorous interactions developed with the FC gas, we have selected various perfluoroalkyl chain lengths (C6F13, C7F15, and C8F17). The length of the (SG)n sequence was set to n = 5, which was found optimal in a previous report [28]. We synthetized three perfluoroalkylated double-chain peptide–lipid

Atherton–Todd reaction: mechanism, scope and applications

• Stéphanie S. Le Corre,
• Mathieu Berchel,
• Hélène Couthon-Gourvès,
• Jean-Pierre Haelters and
• Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2014, 10, 1166–1196, doi:10.3762/bjoc.10.117

• for biological applications. The selected examples to illustrate the applications of the Atherton–Todd reaction mainly cover the past 15 years. Keywords: amphiphiles; flame retardant; lipid conjugates; organophosphorus; phosphoramidate; phosphate; Review 1. Introduction The reaction of