Controlled ring-opening polymerization of N-(3-tert-butoxy-3-oxopropyl) glycine derived N-carboxyanhydrides towards well-defined peptoid-based polyacids,Polymer Chemistry

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Controlled ring-opening polymerization of N-(3-tert-butoxy-3-oxopropyl) glycine derived N-carboxyanhydrides towards well-defined peptoid-based polyacids
Polymer Chemistry ( IF 4.1 ) Pub Date : 2021-1-5 , DOI: 10.1039/d0py01395a
Bailee N. Barrett _{1,

2,

3,

4} , Garrett L. Sternhagen _{1,

2,

3,

4} , Donghui Zhang _{1,

2,

3,

4}

Affiliation

Polypeptoids bearing carboxylic acid groups on the N-substituent are useful building blocks for the construction of peptidomimetic supramolecular assemblies with stimuli-responsive properties. Towards this end, N-(3-tert-butoxy-3-oxopropyl) glycine derived N-carboxyanhydride (^tBuO₂Pr-NCA) has been successfully synthesized and polymerized using primary amine initiators to produce the corresponding poly(N-(3-tert-butoxy-3-oxopropyl) glycine) with molecular weights (M_n) of 5.6–59 kg mol⁻¹ and a narrow molecular weight distribution (PDI = 1.003–1.026). The polymerization was shown to proceed in a controlled manner, evidenced by the good agreement of the experimental molecular weight (M_n) with theoretical values and narrow molecular weight distribution in a wide range of monomer-to-initiator ratios ([M]₀: [I]₀ = 25 : 1–200 : 1), the linear increase of M_n with conversion and the second-order polymerization kinetics. The cloaked carboxyl groups on the poly(N-(3-tert-butoxy-3-oxopropyl) glycine) can be readily unveiled in mild acidic conditions to yield the poly(N-(2-carboxyethyl) glycine), a structural mimic of poly(glutamic acid). The poly(N-(2-carboxyethyl) glycine) polymer is a weak polyelectrolyte whose hydrodynamic size in water can be controlled by the solution pH.

中文翻译：

N-（3-叔丁氧基-3-氧丙基）甘氨酸衍生的N-羧基酸酐向明确的类肽基多元酸的控制的开环聚合

在N-取代基上带有羧酸基团的类多肽是有用的结构单元，用于构建具有刺激响应特性的拟肽超分子组装体。为此，已经成功地合成了N-（3-叔丁氧基-3-氧丙基）甘氨酸衍生的N-羧基酸酐（^t BuO ₂ Pr-NCA），并使用伯胺引发剂进行聚合以生产相应的聚（N-（3 -叔丁氧基-3-氧代丙基甘氨酸），分子量（M _n）为5.6–59 kg mol ^-1分子量分布窄（PDI = 1.003–1.026）。聚合反应以可控的方式进行，证明了实验分子量（M _n）与理论值的良好吻合，并且在较宽的单体引发剂比例范围内[[M] ₀： [I] ₀ = 25：1-200：1），M _n随着转化率的线性增加和二级聚合动力学。聚（N-（3-叔丁氧基-3-氧丙基）甘氨酸）上的隐蔽羧基很容易在弱酸性条件下暴露出来，得到聚（N-（2-羧乙基）甘氨酸），聚谷氨酸的结构模拟物。聚（N-（2-羧乙基）甘氨酸）聚合物是一种弱聚电解质，其在水中的流体力学尺寸可以通过溶液的pH值来控制。

更新日期：2021-01-11

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