Stereoselective Assembly of Hydrogen-Bonded Anionic Cages Dictated by Organophosphate-Based Chiral Nodes
Wei Zuo1, Yu Tao2, Zhipeng Luo2
1Xi'an Key Laboratory of Textile Chemical Engineering Auxiliaries, School of Emvironmental and Chemical Engineering, Xi'an Polytechnic University, Xi'an, 710600, China.
Abstract:
Inspired by the signal transduction function of organophosphates in biological systems, bioactive organophosphates were utilized for the first time as chiral nodes to dictate the stereoselective assembly of hydrogen-bonded anionic cages. Phosphonomycin (antibiotics), tenofovir (antivirals), adenosine monophosphate (natural product, AMP) and clindamycin phosphate (antibiotics) were assembled with an achiral bis-monourea ligand, thereby leading to the stereoselective formation of quadruple or triple helicates. The extent of the stereoselectivity could be enhanced by either lowering the temperature or adding stronger-binding cations as templates. With the chiral anionic cages as the host, some enantioselectivity was achieved when binding chiral quaternary ammonium cations.
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