Stereoselective Assembly of Hydrogen‐Bonded Anionic Cages Dictated by Organophosphate‐Based Chiral Nodes

Author:

Zuo Wei1,Tao Yu2,Luo Zhipeng2,Li Anyang2,Wang Shanshan2,Qiao Xinrui2,Ma Fen2,Jia Chuandong2ORCID

Affiliation:

1. Xi'an Key Laboratory of Textile Chemical Engineering Auxiliaries, School of Emvironmental and Chemical Engineering Xi'an Polytechnic University Xi'an 710600 China

2. Key Laboratory of Synthetic and Natural Functional Molecule of the Ministry of Education Xi'an Key Laboratory of Functional Supramolecular Structure and Materials College of Chemistry and Materials Science Northwest University Xi'an 710069 China

Abstract

AbstractInspired 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.

Funder

National Natural Science Foundation of China

Natural Science Basic Research Program of Shaanxi Province

Natural Science Foundation of Shaanxi Provincial Department of Education

Publisher

Wiley

Subject

General Chemistry,Catalysis

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