3 years ago

Peptide-Appended Permethylated β-Cyclodextrins with Hydrophilic and Hydrophobic Spacers

Peptide-Appended Permethylated β-Cyclodextrins with Hydrophilic and Hydrophobic Spacers
Floris P. J. T. Rutjes, Daniel Zollinger, Abbas H. K. Al Temimi, Thomas J. Boltje, Martin C. Feiters
A novel synthetic methodology, employing a combination of the strain-promoted azide–alkyne cycloaddition and maleimide–thiol reactions, for the preparation of permethylated β-cyclodextrin-linker-peptidyl conjugates is reported. Two different bifunctional maleimide cross-linking probes, the polyethylene glycol containing hydrophilic linker bicyclo[6.1.0] nonyne-maleimide and the hydrophobic 5′-dibenzoazacyclooctyne-maleimide, were attached to azide-appended permethylated β-cyclodextrin. The successfully introduced maleimide function was exploited to covalently graft a cysteine-containing peptide (Ac-Tyr-Arg-Cys-Amide) to produce the target conjugates. The final target compounds were isolated in high purity after purification by isocratic preparative reverse-phase high-performance liquid chromatography. This novel synthetic approach is expected to give access to many different cyclodextrin–linker peptides.

Publisher URL: http://dx.doi.org/10.1021/acs.bioconjchem.7b00319

DOI: 10.1021/acs.bioconjchem.7b00319

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