Tartric Acid-Based Linker for the Solid-Phase Synthesis of C-Terminal Peptide α-Oxo Aldehydes

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Abstract
A novel linker, based on the anchoring of (+)-dimethyl 2,3-O-isopropylidene-d-tartrate to PEGA or PEG-PS solid supports, was developed for the solid-phase synthesis of C-terminal peptide α-oxo aldehydes. Peptide elongation was performed using the 9-fluorenylmethoxycarbonyl/t-Bu chemistry. The peptide and the 1,2-diol were deprotected on the solid phase. Then, a periodic oxidation of the fully deprotected peptidyl-resin led to the simultaneous cleavage of the product from the solid support and to the generation of the α-oxo aldehyde moiety. The methodology allowed the distance between the α-oxo aldehyde and the peptide to be easily modulated. The C-terminal peptide α-oxo aldehydes synthesized in this study were found to be useful partners in hydrazone, thiazolidine, and oxime chemical ligations.