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Structural Insights into Low-Temperature Copolymerization of Thermodegradable Amino Acids Mediated by Pyroglutamic Acid
Macromolecules ( IF 5.1 ) Pub Date : 2024-08-27 , DOI: 10.1021/acs.macromol.4c00614 Davide Carboni 1 , Marta Cadeddu 1, 2 , Luigi Stagi 1 , Roberto Anedda 3 , Luigi Menduti 4 , Luisa De Cola 4 , Luca Malfatti 1 , Plinio Innocenzi 1
Macromolecules ( IF 5.1 ) Pub Date : 2024-08-27 , DOI: 10.1021/acs.macromol.4c00614 Davide Carboni 1 , Marta Cadeddu 1, 2 , Luigi Stagi 1 , Roberto Anedda 3 , Luigi Menduti 4 , Luisa De Cola 4 , Luca Malfatti 1 , Plinio Innocenzi 1
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The demand for biocompatible multifunctional systems for bioimaging is driving the interest in new-generation fluorescent peptide based on nonaromatic amino acids such as l-glutamic acid and l-alanine. In general, due to the high melting points characterizing the zwitterionic structures of amino acids, their thermal polymerization is performed at temperatures between 200 and 300 °C. However, in this range of temperatures, most of the amino acids tend to decompose rather than undergo polymerization. The present work shows how to obtain nonaromatic fluorescent peptides at temperatures as low as 160 °C by copolymerizing l-glutamic acid with other high-melting amino acids, such as l-alanine, l-valine, and l-leucine. The low-temperature conversion of l-glutamic acid into pyroglutamic acid and its copolymerization with another amino acid were fully characterized by infrared and NMR spectroscopies, MS spectrometry, and thermal analysis. The reaction is mediated by the in situ transformation of l-glutamic acid into pyroglutamic acid, which acts simultaneously as an inomer, initiator + monomer, as well as a dispersing agent, allowing copolymerization with another amino acid. The resulting peptides exhibit fluorescent emission in the visible range typical of PGA derivatives, but they also possess a different polar nature that is inherited by the side chain of the second amino acid.
中文翻译：
焦谷氨酸介导的热降解氨基酸低温共聚的结构见解
对用于生物成像的生物相容性多功能系统的需求推动了人们对基于非芳香族氨基酸（如 l-谷氨酸和 l-丙氨酸）的新一代荧光肽的兴趣。通常，由于氨基酸的两性离子结构具有高熔点，因此它们的热聚合在 200 至 300 °C 的温度下进行。 然而，在这个温度范围内，大多数氨基酸倾向于分解而不是聚合。本工作展示了如何通过将 l-谷氨酸与其他高熔点氨基酸（如 l-丙氨酸、l-缬氨酸和 l-亮氨酸）共聚，在低至 160 °C 的温度下获得非芳香族荧光肽。通过红外和 NMR 光谱、MS 光谱和热分析充分表征了 l-谷氨酸在低温下转化为焦谷氨酸及其与另一种氨基酸的共聚反应。该反应是通过 l-谷氨酸原位转化为焦谷氨酸介导的，焦谷氨酸同时充当肌头、引发剂 + 单体以及分散剂，允许与另一种氨基酸共聚。所得肽在 PGA 衍生物的典型可见光范围内表现出荧光发射，但它们也具有不同的极性性质，由第二个氨基酸的侧链遗传。
更新日期：2024-08-27
中文翻译：
焦谷氨酸介导的热降解氨基酸低温共聚的结构见解
对用于生物成像的生物相容性多功能系统的需求推动了人们对基于非芳香族氨基酸（如 l-谷氨酸和 l-丙氨酸）的新一代荧光肽的兴趣。通常，由于氨基酸的两性离子结构具有高熔点，因此它们的热聚合在 200 至 300 °C 的温度下进行。 然而，在这个温度范围内，大多数氨基酸倾向于分解而不是聚合。本工作展示了如何通过将 l-谷氨酸与其他高熔点氨基酸（如 l-丙氨酸、l-缬氨酸和 l-亮氨酸）共聚，在低至 160 °C 的温度下获得非芳香族荧光肽。通过红外和 NMR 光谱、MS 光谱和热分析充分表征了 l-谷氨酸在低温下转化为焦谷氨酸及其与另一种氨基酸的共聚反应。该反应是通过 l-谷氨酸原位转化为焦谷氨酸介导的，焦谷氨酸同时充当肌头、引发剂 + 单体以及分散剂，允许与另一种氨基酸共聚。所得肽在 PGA 衍生物的典型可见光范围内表现出荧光发射，但它们也具有不同的极性性质，由第二个氨基酸的侧链遗传。
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