TY  - JOUR
A1  - Borova, Solomiia
A1  - Schlutt, Christine
A1  - Nickel, Joachim
A1  - Luxenhofer, Robert
T1  - A Transient Initiator for Polypeptoids Postpolymerization α‐Functionalization via Activation of a Thioester Group
JF  - Macromolecular Chemistry and Physics
N2  - 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 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.
KW  - ring-opening polymerization
KW  - bioconjugation
KW  - functional initiators
KW  - polypeptoids
KW  - postpolymerization modification
Y1  - 2022
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-257587
VL  - 223
IS  - 3
ER  -