Hydroxy-directed peptide bond formation from α-amino acid-derived inert esters enabled by boronic acid catalysis

Literature Information

Publication Date 2023-12-13
DOI 10.1039/D3CC04856J
Impact Factor 6.222
Authors

Naoya Takahashi, Airi Takahashi, Naoyuki Shimada


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Abstract

A boronic acid-catalyzed peptide bond formation from α-amino acid methyl esters is described. The catalysis showed high chemoselectivity for β-hydroxy-α-amino esters, affording the peptides in high to excellent yields with high functional group tolerance. This hydroxy-directed peptide bond formation could be applicable to oligopeptide syntheses. This is the first successful example of organoboron-catalyzed peptide bond formation from α-amino acid-derived inert esters.

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