2023
DOI: 10.1002/anie.202300470
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Stereoselective Assembly of Hydrogen‐Bonded Anionic Cages Dictated by Organophosphate‐Based Chiral Nodes

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. T… Show more

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Cited by 8 publications
(7 citation statements)
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“…Consistently, 1 H NMR spectra of 1R , TEA + @ 1R and Cob + @ 1R determined at 298 K or 248 K showed only one set of signals (Figure S27–S28). Therefore, guest binding is no longer effective for increasing the percentage of the predominant diastereomer as observed in our previous studies [12a] …”
Section: Methodsmentioning
confidence: 69%
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“…Consistently, 1 H NMR spectra of 1R , TEA + @ 1R and Cob + @ 1R determined at 298 K or 248 K showed only one set of signals (Figure S27–S28). Therefore, guest binding is no longer effective for increasing the percentage of the predominant diastereomer as observed in our previous studies [12a] …”
Section: Methodsmentioning
confidence: 69%
“…[11c] This observation inspired us to explore chirality modulation by heteroleptic assembly of anionocages. In the current study, two structurally analogous anionocages were synthesized by utilizing a newly developed assembly strategy based on monourea-RPO 3 2À coordination,, [12] including the intrinsically chiral cage 1 and the crown ether functionalized 2 (Scheme 1). Cages 1 and 2 were obtained by treating an enantiopure diimine-linked ligand L 1 or dibenzo-18-crown-6-linked ligand L 2 , respectively, with (TBA) 2 PhPO 3 (TBA = tetrabutylammonium) in a precisely 3 : 2 ratio (Scheme 1, Figure S1-S18 for more details in the Supporting Information).…”
mentioning
confidence: 99%
“…38 Generally, the crystal structures of anionocages can be well retained in common solvents such as acetone, MeCN, DMF, and DMSO, even after being heated at 60 °C for several hours. 28 However, disassembly will be induced by protonic solvents such as water, and ethanol, because these highly competitive solvents can actively participate in the hydrogen bonding with both the ligand and the anion. Currently, most studies of anionocages focus on the structure control and functions derived from their host–guest chemistry have much less been investigated.…”
Section: Discussionmentioning
confidence: 99%
“…22–26 Very recently, our group made advances of this strategy by utilizing monourea instead of the bisurea as the hydrogen binding donor, and organophosphate RPO 3 2− instead of the inorganic phosphate PO 4 3− as the acceptor, generating a new type of anionocage directed and functionalized by organophosphates. 27,28…”
Section: The Historical Background Of Anionocagesmentioning
confidence: 99%
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