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可调谐的肽微球:侧链化学和序列的影响。

Tunable peptoid microspheres: effects of side chain chemistry and sequence.

机构信息

Ralph E. Martin Department of Chemical Engineering, University of Arkansas, 3202 Bell Engineering Center, Fayetteville, AR, USA.

出版信息

Org Biomol Chem. 2013 Jul 21;11(27):4459-64. doi: 10.1039/c3ob40561c.

DOI:10.1039/c3ob40561c
PMID:23715089
Abstract

Peptoids are a versatile family of oligomeric synthetic molecules that can be customized for many applications. The submonomer solid-phase synthesis of peptoids allows for quick and inexpensive manufacturing and the selection of side chains is nearly limitless. In addition, peptoids that include chiral, aromatic side chains form stable helical secondary structure that leads to the potential for the formation of supramolecular assemblies. The effects of water solubility, helical content, charge placement, and side chain bulk on microsphere formation were studied for seven peptoid sequences. We found that secondary structure and partial water solubility were essential for microsphere formation. In addition, charge placement and side chain bulk affect both the ability to form microspheres and the diameter of the microspheres.

摘要

肽缩氨酸是一类用途广泛的低聚物合成分子,可针对多种应用进行定制。肽缩氨酸的亚单体固相合成方法可以快速且廉价地制造,并且侧链的选择几乎是无限的。此外,包含手性、芳香侧链的肽缩氨酸形成稳定的螺旋二级结构,从而有可能形成超分子组装体。本文研究了七个肽缩氨酸序列的亲水性、螺旋含量、电荷分布和侧链体积对微球形成的影响。我们发现二级结构和部分亲水性对微球形成至关重要。此外,电荷分布和侧链体积会影响形成微球的能力和微球的直径。

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1
Tunable peptoid microspheres: effects of side chain chemistry and sequence.可调谐的肽微球:侧链化学和序列的影响。
Org Biomol Chem. 2013 Jul 21;11(27):4459-64. doi: 10.1039/c3ob40561c.
2
Stable helical peptoids via covalent side chain to side chain cyclization.通过共价侧链到侧链环化形成稳定的螺旋拟肽。
Org Biomol Chem. 2008 Aug 21;6(16):2988-94. doi: 10.1039/b806847j. Epub 2008 Jun 26.
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Peptoid microsphere coatings: The effects of helicity, temperature, pH, and ionic strength.类胜肽微球涂层:螺旋性、温度、pH 值和离子强度的影响。
Biopolymers. 2019 Jun;110(6):e23283. doi: 10.1002/bip.23283. Epub 2019 Apr 22.
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Solid-phase submonomer synthesis of peptoid polymers and their self-assembly into highly-ordered nanosheets.类肽聚合物的固相亚单体合成及其自组装成高度有序的纳米片。
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Tuning peptoid secondary structure with pentafluoroaromatic functionality: a new design paradigm for the construction of discretely folded peptoid structures.利用五氟芳族官能团调控类肽二级结构:构建离散折叠类肽结构的新设计范式
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Structural and spectroscopic studies of peptoid oligomers with alpha-chiral aliphatic side chains.具有α-手性脂肪族侧链的类肽低聚物的结构与光谱研究
J Am Chem Soc. 2003 Nov 5;125(44):13525-30. doi: 10.1021/ja037540r.
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J Am Chem Soc. 2001 Jul 18;123(28):6778-84. doi: 10.1021/ja003154n.
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引用本文的文献

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The Diverse World of Foldamers: Endless Possibilities of Self-Assembly.《分子自组装的多样性世界:无穷无尽的可能性》
Molecules. 2020 Jul 18;25(14):3276. doi: 10.3390/molecules25143276.
2
Discovery of Stable and Selective Antibody Mimetics from Combinatorial Libraries of Polyvalent, Loop-Functionalized Peptoid Nanosheets.从多价、环功能化肽纳米片的组合文库中发现稳定且具有选择性的抗体模拟物。
ACS Nano. 2020 Jan 28;14(1):185-195. doi: 10.1021/acsnano.9b07498. Epub 2019 Dec 2.