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.…
Author: | Solomiia Borova, Christine Schlutt, Joachim Nickel, Robert LuxenhoferORCiD |
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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): | CC BY: Creative-Commons-Lizenz: Namensnennung 4.0 International |