Nature Communications (Mar 2023)
Amide-to-ester substitution as a stable alternative to N-methylation for increasing membrane permeability in cyclic peptides
- Yuki Hosono,
- Satoshi Uchida,
- Moe Shinkai,
- Chad E. Townsend,
- Colin N. Kelly,
- Matthew R. Naylor,
- Hsiau-Wei Lee,
- Kayoko Kanamitsu,
- Mayumi Ishii,
- Ryosuke Ueki,
- Takumi Ueda,
- Koh Takeuchi,
- Masatake Sugita,
- Yutaka Akiyama,
- Scott R. Lokey,
- Jumpei Morimoto,
- Shinsuke Sando
Affiliations
- Yuki Hosono
- Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo
- Satoshi Uchida
- Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo
- Moe Shinkai
- Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo
- Chad E. Townsend
- Department of Chemistry and Biochemistry, University of California
- Colin N. Kelly
- Department of Chemistry and Biochemistry, University of California
- Matthew R. Naylor
- Department of Chemistry and Biochemistry, University of California
- Hsiau-Wei Lee
- Department of Chemistry and Biochemistry, University of California
- Kayoko Kanamitsu
- Graduate School of Pharmaceutical Sciences, The University of Tokyo
- Mayumi Ishii
- Graduate School of Pharmaceutical Sciences, The University of Tokyo
- Ryosuke Ueki
- Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo
- Takumi Ueda
- Graduate School of Pharmaceutical Sciences, The University of Tokyo
- Koh Takeuchi
- Graduate School of Pharmaceutical Sciences, The University of Tokyo
- Masatake Sugita
- Department of Computer Science, School of Computing, Tokyo Institute of Technology
- Yutaka Akiyama
- Department of Computer Science, School of Computing, Tokyo Institute of Technology
- Scott R. Lokey
- Department of Chemistry and Biochemistry, University of California
- Jumpei Morimoto
- Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo
- Shinsuke Sando
- Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo
- DOI
- https://doi.org/10.1038/s41467-023-36978-z
- Journal volume & issue
-
Vol. 14,
no. 1
pp. 1 – 14
Abstract
Naturally occurring peptides with high membrane permeability often have backbone ester bonds. Here, the authors investigated the effect of an amide-to-ester substitution on membrane permeability of peptides and found the substitution is useful for improving membrane permeability of cyclic peptides.
