Solid‐Phase Synthesis of Macrocyclic Peptides via Side‐Chain Anchoring of the Ornithine δ‐Amine

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Abstract: Cyclic peptides represent a popular class of macrocyclic drug candidates and therefore their solid phase synthesis has attracted much attention. In this contribution we present an efficient method of side‐chain anchoring for ornithine and lysine residues to be used in the standard Fmoc‐based synthesis of cyclic peptides via on‐resin cyclization. We demonstrate that the side chain of ornithine and lysine protected with N‐Boc‐group can efficiently be converted to the isocyanate which is then immobilized on Wang‐type resin in almost quantitative yield. We further show the synthesis of four biologically active cyclic peptides employing the side chain ornithine anchoring. Our method is at least on a par with the previously reported methodologies in terms of yield and the purity of the final products and is arguably operationally more straightforward.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Solid‐Phase Synthesis of Macrocyclic Peptides via Side‐Chain Anchoring of the Ornithine δ‐Amine ; volume:2022 ; number:11 ; year:2022 ; extent:9
European journal of organic chemistry ; 2022, Heft 11 (2022) (gesamt 9)

Creator: Peterse, Evert
Meeuwenoord, Nico
van den Elst, Hans
van der Marel, Gijsbert A.
Overkleeft, Hermen S.
Filippov, Dmitri V.

DOI: 10.1002/ejoc.202101341

URN: urn:nbn:de:101:1-2022032606440824193973

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 15.08.2025, 7:27 AM CEST

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Peterse, Evert
Meeuwenoord, Nico
van den Elst, Hans
van der Marel, Gijsbert A.
Overkleeft, Hermen S.
Filippov, Dmitri V.

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Solid‐Phase Synthesis of Macrocyclic Peptides via Side‐Chain Anchoring of the Ornithine δ‐Amine

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