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Synfacts 2021; 17(01): 0103
DOI: 10.1055/s-0040-1706076
DOI: 10.1055/s-0040-1706076
Peptide Chemistry
Anhydride-Mediated Peptide Synthesis with C-Terminal Unprotected N-Methylamino Acids
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
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
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
Article published online:
16 December 2020
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