The aggregation and 3D organization of peptide helices are key elements in biology but might also be relevant in nanostructure formation. β-Peptide helices were used as conformationally stable surrogates of α-peptides to be organized by covalently attached nucleobases as recognition units. Because the β-peptide 14-helix conformation allows addressing individual sides of the helix, the aggregation of helices functionalized on two helix flanks was investigated. Nine helices varying in sequence and nucleobase composition were pre-

A total synthesis of the natural product triostin A, wherein the N-methylated depsipeptide scaffold is constructed by solution-phase peptide chemistry followed by disulfide formation and macrocyclization, is described. Finally, the quinoxalines were attached to provide the DNA bisintercalator. Analogs of triostin A were obtained by the successive functionalization of the cyclic depsipeptide with pyrimidine or purine recognition units. The attachment of functional units

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