Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 143, Issue 18, Pages 6792-6797Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.1c02600
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Funding
- Japan Society for the Promotion of Science (JSPS) [JP17H06142]
- Daiko Foundation
- Takeda Science Foundation
- Sumitomo Chemical Co., Ltd., Japan
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A one-pot peptide bond-forming reaction has been developed using unprotected amino acids and peptides, with the help of two different silylating reagents and catalysts. This method is versatile, providing high yields of corresponding peptides without racemization or polymerization.
A one-pot peptide bond-forming reaction has been developed using unprotected amino acids and peptides. Two different silylating reagents, HSi[OCH(CF3)(2)](3) and MTBSTFA, are instrumental for the successful implementation of this approach, being used for the activation and transient masking of unprotected amino acids and peptides at C-termini and N-termini, respectively. Furthermore, CsF and imidazole are used as catalysts, activating HSi[OCH(CF3)(2)](3) and also accelerating chemoselective silylation. This method is versatile as it tolerates side chains that bear a range of functional groups, while providing up to >99% yields of corresponding peptides without any racemization or polymerization.
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