Late-stage peptide C-H alkylation for bioorthogonal C-H activation featuring solid phase peptide synthesis.

ABSTRACT: Methods for the late-stage diversification of structurally complex peptides hold enormous potential for advances in drug discovery, agrochemistry and pharmaceutical industries. While C-H arylations emerged for peptide modifications, they are largely limited to highly reactive, expensive and/or toxic reagents, such as silver(I) salts, in superstoichiometric quantities. In sharp contrast, we herein establish the ruthenium(II)-catalyzed C-H alkylation on structurally complex peptides. The additive-free ruthenium(II)carboxylate C-H activation manifold is characterized by ample substrate scope, racemization-free conditions and the chemo-selective tolerance of otherwise reactive functional groups, such as electrophilic ketone, bromo, ester, amide and nitro substituents. Mechanistic studies by ex

SUBMITTER: Schischko A 

PROVIDER: S-EPMC6685959 | biostudies-literature | 2019 Aug

REPOSITORIES: biostudies-literature