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Peptide-Appended Permethylated ?-Cyclodextrins with Hydrophilic and Hydrophobic Spacers.

ABSTRACT: A novel synthetic methodology, employing a combination of the strain-promoted azide-alkyne cycloaddition and maleimide-thiol reactions, for the preparation of permethylated ?-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 ?-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.

SUBMITTER: Al Temimi AHK

PROVIDER: S-EPMC5561536 | biostudies-literature | 2017 Aug

REPOSITORIES: biostudies-literature

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

Al Temimi Abbas H K AHK Boltje Thomas J TJ Zollinger Daniel D Rutjes Floris P J T FPJT Feiters Martin C MC

Bioconjugate chemistry 20170726 8

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 succe ...[more]

PMID: 28697600

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