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含中央氨基部分的聚(2-乙基-2-恶唑啉)

Poly(2-ethyl-2-oxazoline) Featuring a Central Amino Moiety.

机构信息

Laboratory of Organic and Macromolecular Chemistry (IOMC), Friedrich Schiller University Jena, Humboldtstr. 10, Jena, 07743, Germany.

Jena Center for Soft Matter (JCSM), Friedrich Schiller University Jena, Philosophenweg 7, Jena, 07743, Germany.

出版信息

Macromol Rapid Commun. 2021 Jul;42(13):e2100132. doi: 10.1002/marc.202100132. Epub 2021 May 7.

DOI:10.1002/marc.202100132
PMID:33960561
Abstract

The incorporation of an amino group into a bifunctional initiator for the cationic ring-opening polymerization (CROP) is achieved in a two-step reaction. Detailed kinetic studies using 2-ethyl-2-oxazoline demonstrate the initiators' eligibility for the CROP yielding well-defined polymers featuring molar masses of about 2000 g mol . Deprotection of the phthalimide moiety subsequent to polymerization enables the introduction of a cyclooctyne group in central position of the polymer which is further exploited in a strain-promoted alkyne-azide click reaction (SpAAC) with a Fmoc-protected azido lysine representing a commonly used binding motif for site specific polymer-protein/peptide conjugation. In-depth characterization via electrospray ionization mass spectrometry (ESI) confirms the success of all post polymerization modification steps.

摘要

将氨基基团引入双官能引发剂中,用于阳离子开环聚合(CROP),可通过两步反应实现。使用 2-乙基-2-恶唑啉进行详细的动力学研究表明,这些引发剂适合 CROP,可得到具有约 2000 g/mol 摩尔质量的聚合物,其分子量分布较窄。聚合后脱去邻苯二甲酰亚胺部分,可以在聚合物的中心位置引入一个环辛炔基团,进一步在应变促进的炔基-叠氮点击反应(SpAAC)中利用,其中 Fmoc 保护的叠氮赖氨酸是用于聚合物-蛋白质/肽定点连接的常用结合基序。通过电喷雾电离质谱(ESI)进行的深入表征证实了所有聚合后修饰步骤的成功。

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