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Abstract The first project in this dissertation describes the total synthesis of yaku’amide A analogues. Natural product yaku’amide A possesses potent anticancer activity and exhibits a novel mode of action. However, due to its complex asymmetrical isoleucine dehydroamino acids, the synthesis of this polypeptide poses a unique challenge. Despite the efficient synthesis developed in our lab, the total synthesis of this natural product remains lengthy.
Synthesis and evaluation of potent yaku'amide A analogs† Concordia C. L. Lo,a Daniel Joaquin,a Diego A. Moyá, a Alexander Ramos,a David W. Kastner, a Stephen M. White,a Blake L. Christensen, a Joseph G. Naglich,b William J. Degnenc and Steven L.
A comparative study of the impact of small, medium-sized, and bulky α,β-dehydroamino acids (ΔAAs) on the structure and stability of Balaram’s incipient 310-helical peptide (1) is reported. Replacement of the N-terminal Aib residue of 1 with a ΔAA afforded peptides 2a–c that maintained the 310-helical shape of 1. In contrast, installation of a ΔAA in place of Aib-3 yielded peptides 3a–c that preferred a β-sheet-like conformation.
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