The base pairs and hydrogen-bond network of the 5-Amino-8-(β-L-furanosyl)pyrimido[4,5-d]pyrimidine-2,4(3H,8H)-dione

Supramolecular morphogenesis is a fundamentally important process in fields ranging from structural biology to materials chemistry. Our previous works demonstrated that the sugar structural parameters can decree the supramolecular morphogenesis of Janus-type nucleosides. However, the chiral effect in this regards has not yet been tackled. Here, the self-associated superstructures of J-AT L-ribonucleoside (J-AT-L, 1) was investigated in both solid state and solution by single-crystal X-ray analysis and scanning electron microscope (SEM). The results indicate a high mirror symmetry in both monomeric level and hydrogen bond patterns in solid state between compound 1 and its enantiomeric counterpart J-AT D-ribonucleoside (J-AT-D, 2), except the distinct interactions between A B and B B conformers. The SEM experiments display that J-AT-L forms a porous microsphere-flower-like superstructure, instead of a radial-petal-flower-like superstructure of the D-enantiomer (2), which could be attributed to the different interactions of A-B and B-B conformers among these two series. This study provides for the first time the evidences of how the chiral information of the monomeric J-AT nucleosides is translated into the diverse supramolecular morphologies. (C) 2017 Elsevier B.V. All rights reserved.