Abstract
Linkers play major roles in conjugation chemistry toward the advancement of drug discovery. Two different series of fluorinated linkers were introduced to the backbone of a model peptide using solid phase peptide synthesis. These fluorinated linkers have the potential to conjugate two asymmetrical groups. This has not been done using other fluorinated linkers. This study deals with application of linkers with S, N, and O terminals and reports on the investigation of their chemoselectivity and activity for branching peptide backbones using a chosen model peptide. These fluorinated linkers have unique properties that will make it possible for a large diversity of bioconjugated chemicals for different bioapplications to be designed and synthesized.
Highlights
Conjugation of molecules is a chemical tool with increasing interest in several scientific areas, such as pharmaceuticals or materials
This study investigates the reactivity and site specificity of two new generation of perfluoroaromatic linkers, 2– 6-pentafluoroacetic acid and 2–6-pentafluorothiophenol anchored to the model peptide H-Gly-Phe-Leu-NH-resin (Scheme 1C)
The short peptide H-Gly-Phe-Leu-NH-Resin was built up using solid-phase peptide synthesis (SPPS) methodology. 2– 6-Pentafluorobenzoic acid was safely coupled to the tripeptidyl resin using DIC and OxymaPure to form L1
Summary
Conjugation of molecules is a chemical tool with increasing interest in several scientific areas, such as pharmaceuticals or materials. Both aliphatic and aromatic S containing nucleophiles resulted in triple substitutions in both ortho and para positions (Table 2, #11–14).
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