Peptide Bond Formation of Amino Acids by Transient Masking with Silylating Reagents
Wataru Muramatsu* and Hisashi Yamamoto*
*Molecular Catalyst Research Center, Chubu University, 1200 Matsumoto-cho, Kasugai, Aichi 487-8501, Japan,
Email: muramatsu
isc.chubu.ac.jp, hyamamotoisc.chubu.ac.jp
W. Muramatsu, H. Yamamoto, J. Am. Chem. Soc., 2021, 143, 6792-6797.
DOI: 10.1021/jacs.1c02600
see article for more reactions
Abstract
The use two different silylating reagents (HSi[OCH(CF3)2]3, MTBSTFA) in the presence of CsF and imidazole as catalysts enables a one-pot peptide bond-forming reaction via activation and transient masking at C-termini and N-termini, respectively. This versatile method tolerates various side chains, while providing excellent yields without any racemization or polymerization.
see article for more examples
proposed mechanism
Synthesis of Silacyclic Dipeptides: Peptide Elongation at Both N- and C-Termini of Dipeptide
T. Hattori, H. Yamamoto, J. Am. Chem. Soc., 2022, 144, 1758-1765.
Tantalum-Catalyzed Amidation of Amino Acid Homologues
W. Muramatshu, H. Yamamoto, J. Am. Chem. Soc., 2019, 141, 18926-18931.
Key Words
ID: J48-Y2021
