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A Synthetic Method for Site‐Specific Functionalized Polypeptides: Metal‐Free, Highly Active, and Selective at Room Temperature

Wei Zhao, Yanfeng Lv, Ji Li, Zihao Feng, Yonghao Ni, Nikos Hadjichristidis

2020Angewandte Chemie International Edition26 citationsDOI

Abstract

Functionalized polypeptides have attracted tremendous interest in recent years and found many stimulating applications owing to their tunable physicochemical characteristics including hydrophilicity and stimuli-responsive behavior. The development of new strategies to produce these polymers without metallic contaminants is crucial for their applications in high-value and sensitive domains, such as biomedical, microelectronic, food-packaging, and personal beauty care fields. Herein, a highly efficient strategy to access well-defined site-specific functionalized polypeptides is developed by combining Michael reaction with hydrogen-bonding organocatalytic ROP of NCA. A library of chain-end and chain-middle functionalized polypeptides (14 examples) with predesigned molecular weights and low polydispersities are readily prepared with this approach. Specifically, the whole synthetic process is metal-free, fulfilling high activity and selectivity at room temperature.

Topics & Concepts

Combinatorial chemistryMetalChemistryMaterials scienceOrganic chemistryChemical Synthesis and Analysisbiodegradable polymer synthesis and propertiesSynthetic Organic Chemistry Methods
A Synthetic Method for Site‐Specific Functionalized Polypeptides: Metal‐Free, Highly Active, and Selective at Room Temperature | Litcius