Photochemisch orthogonale Festphasensynthesen (English shop)

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Protecting group strategies in which light can be employed as a “cleavage reagent” represent an interesting extension of the arsenal of chemical methods, since they allow work under mild, substrate-sparing conditions and without contamination of the substrates with reagents.

A photochemically orthogonal protecting group strategy for solid-phase peptide synthesis was developed. To this end, the combination of pivaloyl linkers and NVOC protecting groups was investigated in detail. The photochemically orthogonal method allowed the wavelength-selective excitation of different photolabile protecting groups and afforded the target compounds in high purity without further work-up.

The usefulness of the photolabile pivaloyl linker for the synthesis of larger caged peptides (7–15 amino acids) according to conventional peptide synthesis protocols, followed by photolytic release (uncaging) of the C-terminally bound peptides under in vivo conditions, was investigated.