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序列变化调节类肽在水中的自缔合。

Sequence Changes Modulate Peptoid Self-Association in Water.

作者信息

Fuller Amelia A, Jimenez Christian J, Martinetto Ella K, Moreno Jose L, Calkins Anna L, Dowell Kalli M, Huber Jonathan, McComas Kyra N, Ortega Alberto

机构信息

Department of Chemistry & Biochemistry, Santa Clara University, Santa Clara, CA, United States.

出版信息

Front Chem. 2020 Apr 23;8:260. doi: 10.3389/fchem.2020.00260. eCollection 2020.

DOI:10.3389/fchem.2020.00260
PMID:32391314
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7191062/
Abstract

Peptoids, -substituted glycine oligomers, are a class of diverse and sequence-specific peptidomimetics with wide-ranging applications. Advancing the functional repertoire of peptoids to emulate native peptide and protein functions requires engineering peptoids that adopt regular secondary and tertiary structures. An understanding of how changes to peptoid sequence change structural features, particularly in water-soluble systems, is underdeveloped. To address this knowledge gap, five 15-residue water-soluble peptoids that include naphthalene-functionalized side chains were designed, prepared, and subjected to a structural study using a palette of techniques. Peptoid sequence designs were based on a putative amphiphilic helix peptoid bearing structure-promoting ()--(1-naphthylethyl)glycine residues whose self-association in water has been studied previously. New peptoid variants reported here include sequence changes that influenced peptoid conformational flexibility, functional group patterning (amphiphilicity), and hydrophobicity. Peptoid structures were evaluated and compared using circular dichroism spectroscopy, fluorescence spectroscopy, and size exclusion chromatography. Spectral data confirmed that sequence changes alter peptoids' degree of assembly and the organization of self-assembled structures in aqueous solutions. Insights gained in these studies will inform the design of new water-soluble peptoids with regular structural features, including desirable higher-order (tertiary and quaternary) structural features.

摘要

类肽，即N-取代甘氨酸寡聚物，是一类具有广泛应用的多样且序列特异性的拟肽。要拓展类肽的功能库以模拟天然肽和蛋白质的功能，就需要设计出能形成规则二级和三级结构的类肽。目前对于类肽序列变化如何改变结构特征，尤其是在水溶性体系中的结构特征，了解还不够深入。为填补这一知识空白，设计、制备了五种包含萘官能化侧链的15残基水溶性类肽，并使用一系列技术对其进行结构研究。类肽序列设计基于一种假定的两亲性螺旋类肽结构，该结构含有促进结构形成的（）-（1-萘基乙基）甘氨酸残基，此前已对其在水中的自缔合进行过研究。本文报道的新类肽变体包括影响类肽构象灵活性、官能团模式（两亲性）和疏水性的序列变化。使用圆二色光谱、荧光光谱和尺寸排阻色谱对类肽结构进行了评估和比较。光谱数据证实，序列变化会改变类肽在水溶液中的组装程度和自组装结构的组织方式。这些研究中获得的见解将为设计具有规则结构特征的新型水溶性类肽提供参考，包括理想的高阶（三级和四级）结构特征。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6301/7191062/e367f761e566/fchem-08-00260-g0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6301/7191062/a6bb07c2d1d8/fchem-08-00260-g0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6301/7191062/6940f742417d/fchem-08-00260-g0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6301/7191062/78a8434d3f88/fchem-08-00260-g0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6301/7191062/f20e8b426cff/fchem-08-00260-g0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6301/7191062/2bfef5fbc8d0/fchem-08-00260-g0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6301/7191062/16743015123e/fchem-08-00260-g0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6301/7191062/bbef0159cf11/fchem-08-00260-g0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6301/7191062/e367f761e566/fchem-08-00260-g0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6301/7191062/a6bb07c2d1d8/fchem-08-00260-g0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6301/7191062/6940f742417d/fchem-08-00260-g0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6301/7191062/78a8434d3f88/fchem-08-00260-g0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6301/7191062/f20e8b426cff/fchem-08-00260-g0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6301/7191062/2bfef5fbc8d0/fchem-08-00260-g0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6301/7191062/16743015123e/fchem-08-00260-g0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6301/7191062/bbef0159cf11/fchem-08-00260-g0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6301/7191062/e367f761e566/fchem-08-00260-g0008.jpg

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本文引用的文献

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Functionalized Helical β-Peptoids.功能化螺旋β-拟肽
J Org Chem. 2019 Apr 5;84(7):3762-3779. doi: 10.1021/acs.joc.9b00218. Epub 2019 Mar 19.
2
Fluorinated Aromatic Monomers as Building Blocks To Control α-Peptoid Conformation and Structure.含氟芳香单体作为构建块控制α-肽类似物的构象和结构。
J Am Chem Soc. 2019 Feb 27;141(8):3430-3434. doi: 10.1021/jacs.8b13498. Epub 2019 Feb 15.
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Peptoids advance multidisciplinary research and undergraduate education in parallel: Sequence effects on conformation and lipid interactions.
肽缩氨酸在多学科研究和本科教育中齐头并进：序列对构象和脂质相互作用的影响。
Biopolymers. 2019 Apr;110(4):e23256. doi: 10.1002/bip.23256. Epub 2019 Jan 11.
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Solution effects on the self-association of a water-soluble peptoid.溶液效应对水溶性肽的自组装的影响。
Biopolymers. 2019 Apr;110(4):e23248. doi: 10.1002/bip.23248. Epub 2018 Dec 22.
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Stabilising Peptoid Helices Using Non-Chiral Fluoroalkyl Monomers.使用非手性氟烷基单体稳定肽状螺旋。
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Homogeneous and Robust Polyproline Type I Helices from Peptoids with Nonaromatic α-Chiral Side Chains.具有非芳族α-手性侧链的肽类的均一和稳定的聚脯氨酸 I 型螺旋。
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Balancing the intermolecular forces in peptide amphiphiles for controlling self-assembly transitions.平衡肽两亲分子中的分子间力以控制自组装转变
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A Peptoid Square Helix via Synergistic Control of Backbone Dihedral Angles.通过协同控制主链二面角构建的肽类方螺旋。
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