Journal
ACS CATALYSIS
Volume 10, Issue 16, Pages 9594-9603Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.0c02512
Keywords
amidation; peptides; aminosilane catalysis; hydrosilanes; racemization-free
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Funding
- Japan Society for the Promotion of Science (JSPS), Japan [JP17H06142]
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The epimerization-free formation of peptide bonds is crucial for the development of peptide therapeutics and pharma-ceuticals. Herein, we report a hydrosilane-mediated approach for the construction of peptide bonds between most amino acids under ambient conditions. This concise protocol with an original silylating reagent HSi(OCH(CF3)(2))(3) facilitates the use of amino acids bearing a broad variety of functional groups without any epimerization. up to 98% yield Moreover, a catalytic system using an aminosilane catalyst enables not only the acceleration in silylation of carboxylic acids but also amide synthesis with minimal substrate use (electrophile/nucleophile/silylating reagent = 1:1:1) and waste production (hydrogen gas and a siloxane). These simple and powerful approaches are established as a potentially general paradigm in synthesis of desired peptides in high yields.
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