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Solar and Visible Light Assisted Peptide Coupling
Author(s) -
Mishra Abhaya K.,
Parvari Galit,
Santra Sourav K.,
Bazylevich Andrii,
Dorfman Ortal,
Rahamim Jonatan,
Eichen Yoav,
Szpilman Alex M.
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202011510
Subject(s) - reagent , peptide synthesis , peptide , coupling (piping) , combinatorial chemistry , chemistry , coupling reaction , alkyl , amino acid , halide , organic chemistry , materials science , catalysis , biochemistry , metallurgy
Abstract Amino acid and peptide couplings are widely used in fields related to pharma and materials. Still, current peptide synthesis continues to rely on the use of expensive, water sensitive, and waste‐generating coupling reagents, which are often prepared in multi‐step sequences and used in excess. Herein is described a peptide coupling reaction design that relies mechanistically on sun‐light activation of a 4‐dimethylamino‐pyridine–alkyl halide charge‐transfer complex to generate a novel coupling reagent in situ. The resulting coupling method is rapid, does not require dry solvents or inert atmosphere, and is compatible with all the most common amino acids and protecting groups. Peptide couplings can be run on gram‐scale, without the use of special equipment. This method has a significantly reduced environmental and financial footprint compared to standard peptide coupling reactions. Experimental and computational studies support the proposed mechanism.