Octafunctionalized polyhedral oligosilsesquioxanes as scaffolds: synthesis of peptidyl silsesquioxanes‡

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Frank J. Feher, Kevin D. Wyndham and Mark A. Scialdone


Abstract

The first use of polyhedral silsesquioxanes to organize ensembles of biologically relevant motifs is described. N-Protected amino acids and peptides can be attached to [H2N(CH2)3]8Si8O12 1 and [p-HOCH2C6H4]8Si8O12 2 in either a convergent fashion or a divergent fashion to produce peptidyl silsesquioxanes in excellent yield and purity.


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