Solid-Phase Photochemical Decarboxylative Hydroalkylation of Peptides | Zendy

Mahmoud Elkhalifa | Zendy; Michael Elbaum | Zendy; David M. Chenoweth | Zendy; Gary A. Molander | Zendy

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Solid-Phase Photochemical Decarboxylative Hydroalkylation of Peptides

Author(s) -

Mahmoud Elkhalifa,

Michael Elbaum,

David M. Chenoweth,

Gary A. Molander

Publication year - 2021

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.1c02928

Subject(s) - chemistry , redox , peptide , combinatorial chemistry , photochemistry , iridium , organic chemistry , catalysis , biochemistry

The compatibility of photochemistry with solid-phase peptide synthesis is demonstrated via photochemical hydroalkylation to form C(sp 3 )-C(sp 3 ) bonds between on-resin Giese acceptors and redox-active esters. Both iridium-based photocatalysts and Hantszch ester led to high yields, with final reaction conditions producing full conversions within 30 min under ambient conditions. The chemistry is compatible with a broad range of peptide side chains, redox-active esters, and resin. These conditions represent the first example of photochemical peptide modifications on resin.

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