Stereoselective Assembly of Hydrogen-Bonded Anionic Cages Dictated by Organophosphate-Based Chiral Nodes.
Angew Chem Int Ed Engl
; 62(12): e202300470, 2023 Mar 13.
Article
in En
| MEDLINE
| ID: mdl-36722622
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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01-internacional
Database:
MEDLINE
Language:
En
Journal:
Angew Chem Int Ed Engl
Year:
2023
Document type:
Article
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