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Synfacts 2021; 17(01): 0103
DOI: 10.1055/s-0040-1706076
Peptide Chemistry

Anhydride-Mediated Peptide Synthesis with C-Terminal Unprotected N-Methylamino Acids

Contributor(s):
Hisashi Yamamoto
,
An Wu
Kurasaki H, * Nagaya A, Kobayashi Y, Matsuda A, Matsumoto M, Morimoto K, Taguri T, Takeuchi H, Handa M, Cary DR, Nishizawa N, *, Masuya K. * PeptiDream, Inc., Kawasaki and Nissan Chemical Corporation, Funabashi, Japan
Isostearyl Mixed Anhydrides for the Preparation of N‑Methylated Peptides Using C‑Terminally Unprotected N‑Methylamino Acids.

Org. Lett. 2020;
22: 8039-8043
DOI: 10.1021/acs.orglett.0c02984.
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Key words

mixed anhydrides - silylation reagent - N-methylamino acids

Significance

The synthesis of N-methylated peptides is an important field in organic chemistry and medicinal chemistry. The authors used isostearic acid bromide to generate mixed anhydrides to react with C-terminal-unprotected N-methylamino acids to prepare N-methylated peptides with the assistance of a silylation reagent.


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Comment

Various N-methylated peptides were prepared through the mixed anhydrides intermediate. The reaction proceeds under mild conditions, and the yields of the desired products are good to excellent.


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Publication History

Publication Date:
16 December 2020 (online)

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