Amide-to-ester substitution as a stable alternative to N-methylation for increasing membrane permeability in cyclic peptides
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.
| Main Authors: | , , , , , , , , , , , , , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
Nature Portfolio
2023-03-01
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| Series: | Nature Communications |
| Online Access: | https://doi.org/10.1038/s41467-023-36978-z |
| _version_ | 1797864234496819200 |
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| author | 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 |
| author_facet | 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 |
| author_sort | Yuki Hosono |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-04-09T22:48:28Z |
| format | Article |
| id | doaj.art-a59489e908164722a8c86ea5023eb75f |
| institution | Directory Open Access Journal |
| issn | 2041-1723 |
| language | English |
| last_indexed | 2024-04-09T22:48:28Z |
| publishDate | 2023-03-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Nature Communications |
| spelling | doaj.art-a59489e908164722a8c86ea5023eb75f2023-03-22T11:44:01ZengNature PortfolioNature Communications2041-17232023-03-0114111410.1038/s41467-023-36978-zAmide-to-ester substitution as a stable alternative to N-methylation for increasing membrane permeability in cyclic peptidesYuki Hosono0Satoshi Uchida1Moe Shinkai2Chad E. Townsend3Colin N. Kelly4Matthew R. Naylor5Hsiau-Wei Lee6Kayoko Kanamitsu7Mayumi Ishii8Ryosuke Ueki9Takumi Ueda10Koh Takeuchi11Masatake Sugita12Yutaka Akiyama13Scott R. Lokey14Jumpei Morimoto15Shinsuke Sando16Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of TokyoDepartment of Chemistry and Biotechnology, Graduate School of Engineering, The University of TokyoDepartment of Chemistry and Biotechnology, Graduate School of Engineering, The University of TokyoDepartment of Chemistry and Biochemistry, University of CaliforniaDepartment of Chemistry and Biochemistry, University of CaliforniaDepartment of Chemistry and Biochemistry, University of CaliforniaDepartment of Chemistry and Biochemistry, University of CaliforniaGraduate School of Pharmaceutical Sciences, The University of TokyoGraduate School of Pharmaceutical Sciences, The University of TokyoDepartment of Chemistry and Biotechnology, Graduate School of Engineering, The University of TokyoGraduate School of Pharmaceutical Sciences, The University of TokyoGraduate School of Pharmaceutical Sciences, The University of TokyoDepartment of Computer Science, School of Computing, Tokyo Institute of TechnologyDepartment of Computer Science, School of Computing, Tokyo Institute of TechnologyDepartment of Chemistry and Biochemistry, University of CaliforniaDepartment of Chemistry and Biotechnology, Graduate School of Engineering, The University of TokyoDepartment of Chemistry and Biotechnology, Graduate School of Engineering, The University of TokyoNaturally 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.https://doi.org/10.1038/s41467-023-36978-z |
| spellingShingle | 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 Amide-to-ester substitution as a stable alternative to N-methylation for increasing membrane permeability in cyclic peptides Nature Communications |
| title | Amide-to-ester substitution as a stable alternative to N-methylation for increasing membrane permeability in cyclic peptides |
| title_full | Amide-to-ester substitution as a stable alternative to N-methylation for increasing membrane permeability in cyclic peptides |
| title_fullStr | Amide-to-ester substitution as a stable alternative to N-methylation for increasing membrane permeability in cyclic peptides |
| title_full_unstemmed | Amide-to-ester substitution as a stable alternative to N-methylation for increasing membrane permeability in cyclic peptides |
| title_short | Amide-to-ester substitution as a stable alternative to N-methylation for increasing membrane permeability in cyclic peptides |
| title_sort | amide to ester substitution as a stable alternative to n methylation for increasing membrane permeability in cyclic peptides |
| url | https://doi.org/10.1038/s41467-023-36978-z |
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