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Solid-Phase Photochemical Peptide Homologation Cyclization.

ABSTRACT: Forging new C(sp³)-C(sp³) bonds to central positions within a peptide backbone is critical for the development of new therapeutics and chemical probes. Currently, there are no methods for decarboxylating Asp and Glu side chains solid-phase photochemically or using such radicals to form peptide macrocycles. Herein, electron-donor-acceptor complexes between Hantzsch ester and on-resin peptide N-hydroxyphthalimide radical precursors are used to access these radicals, demonstrated with two-carbon homologations and homologation cyclizations of Atosiban and RGDf.

SUBMITTER: Elbaum MB

PROVIDER: S-EPMC10435287 | biostudies-literature | 2022 Jul

REPOSITORIES: biostudies-literature

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Solid-Phase Photochemical Peptide Homologation Cyclization.

Elbaum Michael B MB Elkhalifa Mahmoud A MA Molander Gary A GA Chenoweth David M DM

Organic letters 20220711 28

Forging new C(sp3)-C(sp3) bonds to central positions within a peptide backbone is critical for the development of new therapeutics and chemical probes. Currently, there are no methods for decarboxylating Asp and Glu side chains solid-phase photochemically or using such radicals to form peptide macrocycles. Herein, electron-donor-acceptor complexes between Hantzsch ester and on-resin peptide N-hydroxyphthalimide radical precursors are used to access these radicals, de ...[more]

PMID: 35816696

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