A Transient Initiator for Polypeptoids Postpolymerization α‐Functionalization via Activation of a Thioester Group

Please always quote using this URN: urn:nbn:de:bvb:20-opus-257587
  • Here, a postpolymerization modification method for an α-terminal functionalized poly-(N-methyl-glycine), also known as polysarcosine, is introduced. 4-(Methylthio)phenyl piperidine-4-carboxylate as an initiator for the ring-opening polymerization of N-methyl-glycine-N-carboxyanhydride followed by oxidation of the thioester group to yield an α-terminal reactive 4-(methylsulfonyl)phenyl piperidine-4-carboxylate polymer is utilized. This represents an activated carboxylic acid terminus, allowing straightforward modification with nucleophiles underHere, a postpolymerization modification method for an α-terminal functionalized poly-(N-methyl-glycine), also known as polysarcosine, is introduced. 4-(Methylthio)phenyl piperidine-4-carboxylate as an initiator for the ring-opening polymerization of N-methyl-glycine-N-carboxyanhydride followed by oxidation of the thioester group to yield an α-terminal reactive 4-(methylsulfonyl)phenyl piperidine-4-carboxylate polymer is utilized. This represents an activated carboxylic acid terminus, allowing straightforward modification with nucleophiles under mild reaction conditions and provides the possibility to introduce a wide variety of nucleophiles as exemplified using small molecules, fluorescent dyes, and model proteins. The new initiator yielded polymers with well-defined molar mass, low dispersity, and high end-group fidelity, as observed by gel permeation chromatography, nuclear magnetic resonance spectroscopy, and matrix-assisted laser desorption/ionization time-of-flight mass spectroscopy. The introduced method can be of great interest for bioconjugation, but requires optimization, especially for protein conjugation.show moreshow less

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Metadaten
Author: Solomiia Borova, Christine Schlutt, Joachim Nickel, Robert LuxenhoferORCiD
URN:urn:nbn:de:bvb:20-opus-257587
Document Type:Journal article
Faculties:Fakultät für Chemie und Pharmazie / Institut für Funktionsmaterialien und Biofabrikation
Medizinische Fakultät / Lehrstuhl für Tissue Engineering und Regenerative Medizin
Language:English
Parent Title (English):Macromolecular Chemistry and Physics
Year of Completion:2022
Volume:223
Issue:3
Article Number:2100331
Source:Macromolecular Chemistry and Physics 2022, 223(3):2100331. DOI: 10.1002/macp.202100331
DOI:https://doi.org/10.1002/macp.202100331
Dewey Decimal Classification:5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften
Tag:bioconjugation; functional initiators; polypeptoids; postpolymerization modification; ring-opening polymerization
Release Date:2022/03/22
Licence (German):License LogoCC BY: Creative-Commons-Lizenz: Namensnennung 4.0 International