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<p>Hydrophobic deep eutectic solvents are introduced as a reaction medium for overcoming the moisture sensitivity of <i>N</i>-carboxyanhydride ring-opening polymerization. Systematic screening identified [camphor][decanoic acid] as an optimal solvent, enabling decagram-scale synthesis of poly(γ-benzyl-L-glutamate) under open-air conditions. The reaction reached 95% conversion in 50 min at 25 °C, and the degree of polymerization closely matched the feed ratios with low dispersity (<i>Đ</i> = ∼1.3). This polymerization also tolerated 80% humidity, water addition, and temperatures up to 85 °C, at which it reached completion within 4 min. The [camphor][decanoic acid] system was compatible with diverse initiators and various amino acid <i>N</i>-carboxyanhydride monomers (Ala, Leu, Bn-His, Tr-Gln, Cbz-Lys, Bn-Cys, and Phe), further supporting the synthesis of block polypeptide copolymers via sequential monomer addition. Additionally, the chirality of DES also has a significant effect on the polymerization rate. These findings establish hydrophobic deep eutectic solvent as a practical, scalable, and water-resistant platform for controlled polypeptide synthesis and offer a general strategy for other water-sensitive reactions.</p>

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Water-resistant and temperature-tolerant ring-opening polymerization of N-carboxyanhydrides in hydrophobic deep eutectic solvents

  • 期刊论文

  • 发表日期：

    2026年1月4日

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  • Yan Zhang,
  • Jia Yao,
  • Wei Li,
  • Qian Zhang,
  • Yonglin Jiang,
  • Yongjia Yang,
  • Zhuo Zhao,
  • Yafei Wang,
  • Ying Guan,
  • Yongjun Zhang

摘要

Hydrophobic deep eutectic solvents are introduced as a reaction medium for overcoming the moisture sensitivity of N-carboxyanhydride ring-opening polymerization. Systematic screening identified [camphor][decanoic acid] as an optimal solvent, enabling decagram-scale synthesis of poly(γ-benzyl-L-glutamate) under open-air conditions. The reaction reached 95% conversion in 50 min at 25 °C, and the degree of polymerization closely matched the feed ratios with low dispersity (Đ = ∼1.3). This polymerization also tolerated 80% humidity, water addition, and temperatures up to 85 °C, at which it reached completion within 4 min. The [camphor][decanoic acid] system was compatible with diverse initiators and various amino acid N-carboxyanhydride monomers (Ala, Leu, Bn-His, Tr-Gln, Cbz-Lys, Bn-Cys, and Phe), further supporting the synthesis of block polypeptide copolymers via sequential monomer addition. Additionally, the chirality of DES also has a significant effect on the polymerization rate. These findings establish hydrophobic deep eutectic solvent as a practical, scalable, and water-resistant platform for controlled polypeptide synthesis and offer a general strategy for other water-sensitive reactions.