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聚(脱氢丙氨酸):荧光多肽的合成、性质及功能多样化。

Poly(dehydroalanine): Synthesis, Properties, and Functional Diversification of a Fluorescent Polypeptide.

机构信息

Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, California 90095, United States.

Department of Bioengineering, University of California, Los Angeles, Los Angeles, California 90095, United States.

出版信息

J Am Chem Soc. 2022 Mar 9;144(9):4214-4223. doi: 10.1021/jacs.2c00383. Epub 2022 Feb 27.

Abstract

Via the design of a new, soluble poly(-alkyl-l-cysteine) precursor, a route was developed for the successful preparation of long-chain poly(dehydroalanine), , as well as the incorporation of dehydroalanine residues and segments into copolypeptides. Based on experimental and computational data, was found to adopt a previously unobserved "hybrid coil" structure, which combines the elements of 2-helical and 3-helical conformations. Analysis of the spectroscopic properties of revealed that it possesses a strong inherent blue fluorescence, which may be amenable for use in imaging applications. also contains reactive electrophilic groups that allowed its efficient modification to functionalized polypeptides after reactions under mild conditions with thiol and amine nucleophiles. The combined structural, spectroscopic, and reactivity properties of make it a unique reactive and fluorescent polypeptide component for utilization in self-assembled biomaterials.

摘要

通过设计一种新的可溶聚(-烷基-L-半胱氨酸)前体,开发出一种成功制备长链聚(脱氢丙氨酸)()的方法,以及将脱氢丙氨酸残基和片段掺入共多肽中。基于实验和计算数据,发现 采用了以前未观察到的“混合线圈”结构,该结构结合了 2-螺旋和 3-螺旋构象的元素。对 的光谱性质进行分析表明,它具有很强的固有蓝色荧光,可能适用于成像应用。 还含有反应性亲电基团,允许其在与巯基和胺亲核试剂在温和条件下反应后,有效地修饰为功能性多肽。 的结构、光谱和反应性能使其成为用于自组装生物材料的独特反应性和荧光多肽成分。

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