Open AccessSolid-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 , photochemistry , combinatorial chemistry , 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.