Umpolung Ala^B Reagents for the Synthesis of Non-Proteogenic Amino Acids, Peptides and Proteins.

ABSTRACT: Non-proteogenic amino acids and functionalized peptides are important motifs in modern drug discovery. Here we report that Ala^B can serve as universal building blocks in the synthesis of a diverse collection of modified amino acids, peptides, and proteins. First, we develop the synthesis of Ala^B from redox-active esters of aspartic acid resulting in a series of β-boronoalanine derivatives. Next, we show that Ala^B can be integrated into automated oligopeptide solid-phase synthesis. Ala^B is compatible with common transformations used in preparative peptide chemistry such as native chemical ligation and radical desulfurization as showcased by total synthesis of Ala^B -containing ubiquitin. Furthermore, Ala^B reagents participate

SUBMITTER: Zhu F 

PROVIDER: S-EPMC9329247 | biostudies-literature | 2022 Aug

REPOSITORIES: biostudies-literature