Synthesis of lactam-bridged cyclic peptides using sequential olefin metathesis and diimide reduction reactions

Aihara, Keisuke; Inokuma, Tsubasa; Komiya, Chiaki; Shigenaga, Akira; Otaka, Akira

doi:10.1016/j.tet.2015.04.093

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Use this link to cite this item : https://repo.lib.tokushima-u.ac.jp/111884

ID	111884
Author	Aihara, Keisuke Tokushima University Inokuma, Tsubasa Tokushima University Tokushima University Educator and Researcher Directory KAKEN Search Researchers Komiya, Chiaki Tokushima University Shigenaga, Akira Tokushima University KAKEN Search Researchers Otaka, Akira Tokushima University Tokushima University Educator and Researcher Directory KAKEN Search Researchers
Keywords	Lactam-bridged peptide Cyclic peptide Ring-closing metathesis Fmoc solid-phase peptide synthesis Diimide reduction
Content Type	Journal Article
Description	A new approach has been developed for the synthesis of lactam-bridged cyclic peptides. Following the introduction of N-allyl glutamine and α-allylglycine into the peptide backbone, the side chains of these residues were subjected to a cyclization reaction by ring-closing metathesis (RCM). Reduction of the resulting peptide bearing olefin moiety was achieved using diimide, which was generated in situ from o-nitrobenzenesulfonyl hydrazine and piperidine, gave the corresponding saturated cyclic peptides.
Journal Title	Tetrahedron
ISSN	00404020
NCID	AA00861787 AA11539786
Publisher	Elsevier
Volume	71
Issue	24
Start Page	4183
End Page	4191
Published Date	2015-05-01
Rights	© 2015. This manuscript version is made available under the CC-BY-NC-ND 4.0 license http://creativecommons.org/licenses/by-nc-nd/4.0/
EDB ID	293936
DOI (Published Version)	10.1016/j.tet.2015.04.093
URL ( Publisher's Version )	https://doi.org/10.1016/j.tet.2015.04.093
FullText File	tet_71_24_4183.pdf 660 KB tet_71_24_4183_si.pdf 2.99 MB
language	eng
TextVersion	Author
departments	Pharmaceutical Sciences