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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: muramatsuisc.chubu.ac.jp, hyamamotoisc.chubu.ac.jp

W. Muramatsu, H. Yamamoto, J. Am. Chem. Soc., 2021, 143, 6792-6797.

DOI: 10.1021/jacs.1c02600 (free Supporting Information)


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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.

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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

amides


ID: J48-Y2021