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

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

Authors

    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
CrossrefPubMedSearch in Google Scholar
Further Information
 
 PDF Download Permissions and Reprints

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.


 

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.


 

 

Publication History

Article published online:
16 December 2020

© 2020. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany


  Permissions and Reprints