PubMed · 13753453
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T KOSUGE, H KAMIYA. 1960-12-24. A new cyclic dipeptide from peptone.. https://doi.org/10.1038/1881112a0
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Enantiopure (2S)-N-(Boc)-3-(6-methylpyridazinyl)alanine (14) has been synthesized to serve as a phenylalanine analog lacking significant pi-donor capability. Two approaches were developed to furnish the target compound from L-aspartic acid as chiral educt in respectively six and nine steps and 13% and 12% yields. In both routes, a key homoallylic ketone intermediate was synthesized by a copper-catalyzed cascade addition of vinylmagnesium bromide to a carboxylic ester. Dipeptide models Ac-Xaa-Pro-NHMe (21a-c) were prepared and the relative populations of prolyl cis- and trans-amide isomers were measured in chloroform, dimethylsulfoxide, and water by proton NMR spectroscopy in order to assess the significance of the electron density of the neighboring aromatic residue on the prolyl amide geometry.
In the last few years dipeptides with two hydrophobic residues (hydrophobic dipeptides) have emerged as an unexpected source of stable microporous organic materials. Supramolecular self-assembly of the rather small building blocks is dictated by stringent demands on the hydrogen-bond formation by the peptide main chains and the aggregation of hydrophobic entities in the side chains. A systematic survey of structures derived from single-crystal X-ray diffraction studies has revealed the existence of two large classes of structures, differing in the dimensionality of the hydrogen-bonding patterns in the crystals and the nature of the channels. The present review summarizes the structural properties of the microporous dipeptides and discusses their potential applications.
A brief account on the historical events leading to the discovery of self-assembling dendrons that generate self-organizable supramolecular dendrimers, or supramolecular polymers, and self-organizable dendronized polymers is provided. These building blocks were accessed by an accelerated design strategy that involves structural and retrostructural analysis of periodic and quasi-periodic assemblies. This design strategy mediated the discovery of porous helical supramolecular structures that self-assembled from dendritic dipeptides. Helical porous columns are the closest mimics of biologically related structures, such as tobacco mosaic virus coat, porous transmembrane proteins, porous pathogens and antibiotics. It is expected that this concept will allow one to investigate the structural origin of functions in synthetic supramolecular materials.