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Columnar Assembly of Cyclic beta-Amino Acid Functionalized with Pyranose Rings

机译：吡喃糖环官能化的环状β-氨基酸的柱状组装

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摘要

A novel cyclic trimer and tetramer of protected beta-glycamino acids were synthesized and investigated on conformation and assembly formation.A characteristic point of these cyclic beta-glycamino acids is their better solubility than other cyclic beta-amino acids due to the pyranose rings.Thus,the assembling process of the cyclic molecules could be examined by CD or NMR spectroscopy.FT-IR and NMR measurements and geometry optimization revealed a highly symmetric and planar conformation for each cyclic beta-peptide with all-trans amide groups.The amide groups in the cyclic peptides took a vertical orientation against the cyclic skeleton to be suitably arranged for intermolecular hydrogen bonds,which should promote formation of molecular assembly in a columnar structure through molecular stacking.These cyclic beta-peptides were successfully crystallized to yield rod-shaped molecular assemblies in nanometer sizes.Evidence for the columnar structure in the crystals was obtained by electron diffraction analysis,which showed a layer spacing of ca.4.8 A.Interestingly,the molecular assembly of the cyclic trimer showed a high aspect ratio,width less than 40 nm,and length more than 2 mu m,suggesting stable molecular stacking in the column.
机译：合成了一种新型的受保护的β-糖基氨基酸的环状三聚体和四聚体，并对其构象和组装形成进行了研究。 FT-IR和NMR测量以及几何优化表明，每个带有全反酰胺基团的环状β肽具有高度对称性和平面构象，可以通过CD或NMR光谱法检查环状分子的组装过程。环状肽相对于环状骨架呈垂直取向，以适合分子间氢键排列，应通过分子堆叠促进柱状结构中分子组装的形成。这些环状β肽成功结晶产生棒状分子组装通过电子获得晶体中柱状结构的证据衍射分析显示层间距约为4.8A。有趣的是，环状三聚体的分子组装体显示出高的长径比，宽度小于40 nm，长度大于2μm，这表明色谱柱中的分子堆积稳定。

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