Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 60, Issue 22, Pages 12406-12412Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202011510
Keywords
charge-transfer complex; halogen bonding; peptide coupling; solar light; visible light
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Funding
- Israel Science Foundation [1914/15]
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This study presents a peptide coupling reaction design that relies on sun-light activation to generate a novel coupling reagent in situ. The method is rapid, does not require dry solvents or inert atmosphere, and is compatible with all common amino acids and protecting groups. The proposed mechanism is supported by experimental and computational studies.
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.
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