Unusual Pseudopeptides: Syntheses and Structural Analyses of Ethylenediprolyl Peptides and Their Metal Complexes with Cu(II) Ion,The Journal of Organic Chemistry

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Unusual Pseudopeptides: Syntheses and Structural Analyses of Ethylenediprolyl Peptides and Their Metal Complexes with Cu(II) Ion
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2021-11-16 , DOI: 10.1021/acs.joc.1c01676
Manish K Gupta _{1,

2} , Chinmay K Jena _{1,

2} , Chenikkayala Balachandra _{1,

2} , Nagendra K Sharma _{1,

2}

Affiliation

The synthetic unnatural amino acids and their peptides as peptidomimetics have shown remarkable structural and functional properties. In the repertoire of synthetic peptides, pseudopeptides have emerged as attractive small peptidomimetics that are capable of forming the characteristic secondary structures in the solid/solution phase, as in natural peptides. This report describes the synthesis and structural analyses of novel pseudopeptides as ethylenediprolyl (etpro) tetra/hexapeptides, comprising a chiral diaminedicarboxylate scaffold. Their NMR and CD spectral analyses strongly support the formation of the β-turn-type structures in organic solvents (ACN/MeOH). Further, the single-crystal X-ray studies of tetrapseudopeptide confirm the formation of a unique self-assembly structure as β-strand type in the solid state through hydrogen bonding. Importantly, their diamine moiety influences the formation of Cu-complexes with Cu(II) ions. A tetrapseudopeptide monocarboxylate-Cu(II) complex forms the single crystal that is studied by the single-crystal X-ray diffractometer. The crystal structure of the tetrapseudopeptide-Cu(II) complex confirms the formation of the distorted square planar geometry structure, almost like the amyloid β(Aβ)-peptide-Cu(II) complex structural geometry. Hence, these etpro-pseudopeptides are emerging peptidomimatics that form β-turn types of structures and metal complexes mainly with Cu(II) ions. These molecules could be considered for the development of peptide-based catalysts and peptide-based therapeutic drug candidates.

中文翻译：

不寻常的拟肽：亚乙基二脯氨酸及其与铜 (II) 离子的金属配合物的合成和结构分析

合成的非天然氨基酸及其肽作为肽模拟物已显示出显着的结构和功能特性。在合成肽的所有组成部分中，假肽已成为有吸引力的小肽模拟物，它们能够在固相/溶液相中形成特征性二级结构，就像在天然肽中一样。本报告描述了新型假肽的合成和结构分析，如乙烯二脯氨酸 ( etpro)四/六肽，包含手性二胺二羧酸盐支架。他们的 NMR 和 CD 光谱分析强烈支持在有机溶剂 (ACN/MeOH) 中形成 β-转角型结构。此外，四伪肽的单晶 X 射线研究证实，通过氢键在固态下形成了独特的 β 链型自组装结构。重要的是，它们的二胺部分会影响与 Cu(II) 离子形成的 Cu 配合物。四伪肽单羧酸盐-Cu(II) 复合物形成单晶，由单晶 X 射线衍射仪研究。四伪肽-Cu(II) 复合物的晶体结构证实了扭曲的方形平面几何结构的形成，几乎类似于淀粉样蛋白 β(Aβ)-肽-Cu(II) 复合物的结构几何形状。因此，这些etpro- pseudopeptides 是一种新兴的拟肽，主要与 Cu(II) 离子形成β-转角类型的结构和金属络合物。这些分子可以考虑用于开发基于肽的催化剂和基于肽的治疗药物候选物。

更新日期：2021-12-03

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