Interplay of Stereochemistry and Charge Governs Guest Binding in Flexible Zn II 4 L 4 Cages
Here, we report the synthesis of a family of chiral Zn L tetrahedral cages by subcomponent self-assembly. These cages contain a flexible trialdehyde subcomponent that allows them to adopt stereochemically distinct configurations. The incorporation of enantiopure 1-phenylethylamine produced Δ and Λ e...
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| Veröffentlicht in: | Journal of the American Chemical Society 2024-11, Vol.146 (47), p.32730 |
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| creator | Xue, Weichao Benchimol, Elie Walther, Alexandre Ouyang, Nianfeng Holstein, Julian J Ronson, Tanya K Openy, Joseph Zhou, Yujuan Wu, Kai Chowdhury, Rituparno Clever, Guido H Nitschke, Jonathan R |
| description | Here, we report the synthesis of a family of chiral Zn
L
tetrahedral cages by subcomponent self-assembly. These cages contain a flexible trialdehyde subcomponent that allows them to adopt stereochemically distinct configurations. The incorporation of enantiopure 1-phenylethylamine produced Δ
and Λ
enantiopure cages, in contrast to the racemates that resulted from the incorporation of achiral 4-methoxyaniline. The stereochemistry of these Zn
L
tetrahedra was characterized by X-ray crystallography and chiroptical spectroscopy. Upon binding the enantiopure natural product podocarpic acid, the Zn
stereocenters of the enantiopure Δ
-Zn
L
cage retained their Δ handedness. In contrast, the metal stereocenters of the enantiomeric Λ
-Zn
L
cage underwent inversion to a Δ configuration upon encapsulation of the same guest. Insights gained about the stereochemical communication between host and guest enabled the design of a process for acid/base-responsive guest uptake and release, which could be followed by chiroptical spectroscopy. |
| doi_str_mv | 10.1021/jacs.4c12320 |
| format | Article |
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L
tetrahedral cages by subcomponent self-assembly. These cages contain a flexible trialdehyde subcomponent that allows them to adopt stereochemically distinct configurations. The incorporation of enantiopure 1-phenylethylamine produced Δ
and Λ
enantiopure cages, in contrast to the racemates that resulted from the incorporation of achiral 4-methoxyaniline. The stereochemistry of these Zn
L
tetrahedra was characterized by X-ray crystallography and chiroptical spectroscopy. Upon binding the enantiopure natural product podocarpic acid, the Zn
stereocenters of the enantiopure Δ
-Zn
L
cage retained their Δ handedness. In contrast, the metal stereocenters of the enantiomeric Λ
-Zn
L
cage underwent inversion to a Δ configuration upon encapsulation of the same guest. Insights gained about the stereochemical communication between host and guest enabled the design of a process for acid/base-responsive guest uptake and release, which could be followed by chiroptical spectroscopy.</description><identifier>ISSN: 0002-7863</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/jacs.4c12320</identifier><identifier>PMID: 39541177</identifier><language>eng</language><publisher>United States</publisher><ispartof>Journal of the American Chemical Society, 2024-11, Vol.146 (47), p.32730</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c607-df5bc2137afc2b8049b05ae270040ddf6c428e0bb946e7e52fce2c85c7be41c03</cites><orcidid>0000-0002-6917-3685 ; 0000-0001-7613-9920 ; 0000-0002-8376-9485 ; 0000-0001-8458-3060 ; 0000-0002-8385-7805 ; 0000-0002-4060-5122 ; 0000-0001-6336-7836</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,2765,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/39541177$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Xue, Weichao</creatorcontrib><creatorcontrib>Benchimol, Elie</creatorcontrib><creatorcontrib>Walther, Alexandre</creatorcontrib><creatorcontrib>Ouyang, Nianfeng</creatorcontrib><creatorcontrib>Holstein, Julian J</creatorcontrib><creatorcontrib>Ronson, Tanya K</creatorcontrib><creatorcontrib>Openy, Joseph</creatorcontrib><creatorcontrib>Zhou, Yujuan</creatorcontrib><creatorcontrib>Wu, Kai</creatorcontrib><creatorcontrib>Chowdhury, Rituparno</creatorcontrib><creatorcontrib>Clever, Guido H</creatorcontrib><creatorcontrib>Nitschke, Jonathan R</creatorcontrib><title>Interplay of Stereochemistry and Charge Governs Guest Binding in Flexible Zn II 4 L 4 Cages</title><title>Journal of the American Chemical Society</title><addtitle>J Am Chem Soc</addtitle><description>Here, we report the synthesis of a family of chiral Zn
L
tetrahedral cages by subcomponent self-assembly. These cages contain a flexible trialdehyde subcomponent that allows them to adopt stereochemically distinct configurations. The incorporation of enantiopure 1-phenylethylamine produced Δ
and Λ
enantiopure cages, in contrast to the racemates that resulted from the incorporation of achiral 4-methoxyaniline. The stereochemistry of these Zn
L
tetrahedra was characterized by X-ray crystallography and chiroptical spectroscopy. Upon binding the enantiopure natural product podocarpic acid, the Zn
stereocenters of the enantiopure Δ
-Zn
L
cage retained their Δ handedness. In contrast, the metal stereocenters of the enantiomeric Λ
-Zn
L
cage underwent inversion to a Δ configuration upon encapsulation of the same guest. Insights gained about the stereochemical communication between host and guest enabled the design of a process for acid/base-responsive guest uptake and release, which could be followed by chiroptical spectroscopy.</description><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNo9kMFKAzEQhoMotlZvniUP4NZJNtlsj7rYulDwYE96WJLspN2yzZakFfv2bmn1MMz88DH8fITcMxgz4OxprW0cC8t4yuGCDJnkkEjGs0syBACeqDxLB-QmxnUfBc_ZNRmkEykYU2pIvkq_w7Bt9YF2jn70N3Z2hZsm7sKBal_TYqXDEums-8bgI53tMe7oS-Prxi9p4-m0xZ_GtEg_PS1LKui8n0IvMd6SK6fbiHfnPSKL6euieEvm77OyeJ4nNgOV1E4ay1mqtLPc5CAmBqRGrvq2UNcus31pBGMmIkOFkjuL3ObSKoOCWUhH5PH01oYuxoCu2oZmo8OhYlAdFVVHRdVZUY8_nPDt3myw_of_nKS_TKNhmA</recordid><startdate>20241127</startdate><enddate>20241127</enddate><creator>Xue, Weichao</creator><creator>Benchimol, Elie</creator><creator>Walther, Alexandre</creator><creator>Ouyang, Nianfeng</creator><creator>Holstein, Julian J</creator><creator>Ronson, Tanya K</creator><creator>Openy, Joseph</creator><creator>Zhou, Yujuan</creator><creator>Wu, Kai</creator><creator>Chowdhury, Rituparno</creator><creator>Clever, Guido H</creator><creator>Nitschke, Jonathan R</creator><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-6917-3685</orcidid><orcidid>https://orcid.org/0000-0001-7613-9920</orcidid><orcidid>https://orcid.org/0000-0002-8376-9485</orcidid><orcidid>https://orcid.org/0000-0001-8458-3060</orcidid><orcidid>https://orcid.org/0000-0002-8385-7805</orcidid><orcidid>https://orcid.org/0000-0002-4060-5122</orcidid><orcidid>https://orcid.org/0000-0001-6336-7836</orcidid></search><sort><creationdate>20241127</creationdate><title>Interplay of Stereochemistry and Charge Governs Guest Binding in Flexible Zn II 4 L 4 Cages</title><author>Xue, Weichao ; Benchimol, Elie ; Walther, Alexandre ; Ouyang, Nianfeng ; Holstein, Julian J ; Ronson, Tanya K ; Openy, Joseph ; Zhou, Yujuan ; Wu, Kai ; Chowdhury, Rituparno ; Clever, Guido H ; Nitschke, Jonathan R</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c607-df5bc2137afc2b8049b05ae270040ddf6c428e0bb946e7e52fce2c85c7be41c03</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Xue, Weichao</creatorcontrib><creatorcontrib>Benchimol, Elie</creatorcontrib><creatorcontrib>Walther, Alexandre</creatorcontrib><creatorcontrib>Ouyang, Nianfeng</creatorcontrib><creatorcontrib>Holstein, Julian J</creatorcontrib><creatorcontrib>Ronson, Tanya K</creatorcontrib><creatorcontrib>Openy, Joseph</creatorcontrib><creatorcontrib>Zhou, Yujuan</creatorcontrib><creatorcontrib>Wu, Kai</creatorcontrib><creatorcontrib>Chowdhury, Rituparno</creatorcontrib><creatorcontrib>Clever, Guido H</creatorcontrib><creatorcontrib>Nitschke, Jonathan R</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><jtitle>Journal of the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Xue, Weichao</au><au>Benchimol, Elie</au><au>Walther, Alexandre</au><au>Ouyang, Nianfeng</au><au>Holstein, Julian J</au><au>Ronson, Tanya K</au><au>Openy, Joseph</au><au>Zhou, Yujuan</au><au>Wu, Kai</au><au>Chowdhury, Rituparno</au><au>Clever, Guido H</au><au>Nitschke, Jonathan R</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Interplay of Stereochemistry and Charge Governs Guest Binding in Flexible Zn II 4 L 4 Cages</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J Am Chem Soc</addtitle><date>2024-11-27</date><risdate>2024</risdate><volume>146</volume><issue>47</issue><spage>32730</spage><pages>32730-</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><abstract>Here, we report the synthesis of a family of chiral Zn
L
tetrahedral cages by subcomponent self-assembly. These cages contain a flexible trialdehyde subcomponent that allows them to adopt stereochemically distinct configurations. The incorporation of enantiopure 1-phenylethylamine produced Δ
and Λ
enantiopure cages, in contrast to the racemates that resulted from the incorporation of achiral 4-methoxyaniline. The stereochemistry of these Zn
L
tetrahedra was characterized by X-ray crystallography and chiroptical spectroscopy. Upon binding the enantiopure natural product podocarpic acid, the Zn
stereocenters of the enantiopure Δ
-Zn
L
cage retained their Δ handedness. In contrast, the metal stereocenters of the enantiomeric Λ
-Zn
L
cage underwent inversion to a Δ configuration upon encapsulation of the same guest. Insights gained about the stereochemical communication between host and guest enabled the design of a process for acid/base-responsive guest uptake and release, which could be followed by chiroptical spectroscopy.</abstract><cop>United States</cop><pmid>39541177</pmid><doi>10.1021/jacs.4c12320</doi><orcidid>https://orcid.org/0000-0002-6917-3685</orcidid><orcidid>https://orcid.org/0000-0001-7613-9920</orcidid><orcidid>https://orcid.org/0000-0002-8376-9485</orcidid><orcidid>https://orcid.org/0000-0001-8458-3060</orcidid><orcidid>https://orcid.org/0000-0002-8385-7805</orcidid><orcidid>https://orcid.org/0000-0002-4060-5122</orcidid><orcidid>https://orcid.org/0000-0001-6336-7836</orcidid></addata></record> |
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| source | ACS Publications |
| title | Interplay of Stereochemistry and Charge Governs Guest Binding in Flexible Zn II 4 L 4 Cages |
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