Fluorous-Phase- and Chiral-Axis-Enhanced Fluorescent Sensitivity and Chemoselectivity for Cysteine Recognition
Highly fluorinated naphthyl aldehyde and binaphthyl aldehyde ( )- were designed and synthesized for fluorous-phase-based sensing. Greatly enhanced sensitivity and chemoselectivity in going from to ( )- in the fluorescent detection of cysteine has been discovered. This is attributed to the increased...
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| Veröffentlicht in: | Organic letters 2025-01 |
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| creator | Yang, Jiaqiao Qian, Cheng Su, Hanyu Zhang, Ji Yu, Shanshan Yu, Xiaoqi Pu, Lin |
| description | Highly fluorinated naphthyl aldehyde
and binaphthyl aldehyde (
)-
were designed and synthesized for fluorous-phase-based sensing. Greatly enhanced sensitivity and chemoselectivity in going from
to (
)-
in the fluorescent detection of cysteine has been discovered. This is attributed to the increased structural rigidity of the axially chiral binaphthyl unit in (
)-
upon reaction with cysteine to form the corresponding thiazolidine product. The fluorous-phase-based detection of cysteine not only can allow the analysis to be conducted in a phase away from the interference of other organic and inorganic species but also results in significantly increased fluorescence response. |
| doi_str_mv | 10.1021/acs.orglett.4c04175 |
| format | Article |
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and binaphthyl aldehyde (
)-
were designed and synthesized for fluorous-phase-based sensing. Greatly enhanced sensitivity and chemoselectivity in going from
to (
)-
in the fluorescent detection of cysteine has been discovered. This is attributed to the increased structural rigidity of the axially chiral binaphthyl unit in (
)-
upon reaction with cysteine to form the corresponding thiazolidine product. The fluorous-phase-based detection of cysteine not only can allow the analysis to be conducted in a phase away from the interference of other organic and inorganic species but also results in significantly increased fluorescence response.</description><identifier>ISSN: 1523-7060</identifier><identifier>ISSN: 1523-7052</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/acs.orglett.4c04175</identifier><identifier>PMID: 39761029</identifier><language>eng</language><publisher>United States</publisher><ispartof>Organic letters, 2025-01</ispartof><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c1811-158fbdbe84cd759b64ae82c2e8efc05eefba2cd5d9018c82a20e554f86587ca73</cites><orcidid>0000-0003-1719-6137 ; 0000-0002-5190-5905 ; 0000-0001-8698-3228 ; 0000-0002-2238-5824</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,777,781,2752,27905,27906</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/39761029$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Yang, Jiaqiao</creatorcontrib><creatorcontrib>Qian, Cheng</creatorcontrib><creatorcontrib>Su, Hanyu</creatorcontrib><creatorcontrib>Zhang, Ji</creatorcontrib><creatorcontrib>Yu, Shanshan</creatorcontrib><creatorcontrib>Yu, Xiaoqi</creatorcontrib><creatorcontrib>Pu, Lin</creatorcontrib><title>Fluorous-Phase- and Chiral-Axis-Enhanced Fluorescent Sensitivity and Chemoselectivity for Cysteine Recognition</title><title>Organic letters</title><addtitle>Org Lett</addtitle><description>Highly fluorinated naphthyl aldehyde
and binaphthyl aldehyde (
)-
were designed and synthesized for fluorous-phase-based sensing. Greatly enhanced sensitivity and chemoselectivity in going from
to (
)-
in the fluorescent detection of cysteine has been discovered. This is attributed to the increased structural rigidity of the axially chiral binaphthyl unit in (
)-
upon reaction with cysteine to form the corresponding thiazolidine product. The fluorous-phase-based detection of cysteine not only can allow the analysis to be conducted in a phase away from the interference of other organic and inorganic species but also results in significantly increased fluorescence response.</description><issn>1523-7060</issn><issn>1523-7052</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2025</creationdate><recordtype>article</recordtype><recordid>eNo9kM1OwzAQhC0EoqXwBEgoRy4udhInzrGKWkCqBOLnbDnOpjVK7GIniL49hoaedrWamd39ELqmZE5JTO-k8nPrNi30_TxVJKU5O0FTyuIE54TFp8c-IxN04f0HITRMinM0SYo8CxnFFJlVO1hnB4-ft9IDjqSpo3KrnWzx4lt7vDRbaRTU0Z8QvALTR69gvO71l-73owE666EFNQ4b66Jy73vQBqIXUHZjgt6aS3TWyNbD1Vhn6H21fCsf8Prp_rFcrLGinFJMGW-qugKeqjpnRZWlEnisYuDQKMIAmkrGqmZ1QShXPJYxAcbShmeM50rmyQzdHnJ3zn4O4HvR6XB620oD4VmRUEY5J1kANEPJQaqc9d5BI3ZOd9LtBSXiF7QIoMUIWoygg-tmXDBUHdRHzz_Z5AdBk39l</recordid><startdate>20250106</startdate><enddate>20250106</enddate><creator>Yang, Jiaqiao</creator><creator>Qian, Cheng</creator><creator>Su, Hanyu</creator><creator>Zhang, Ji</creator><creator>Yu, Shanshan</creator><creator>Yu, Xiaoqi</creator><creator>Pu, Lin</creator><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-1719-6137</orcidid><orcidid>https://orcid.org/0000-0002-5190-5905</orcidid><orcidid>https://orcid.org/0000-0001-8698-3228</orcidid><orcidid>https://orcid.org/0000-0002-2238-5824</orcidid></search><sort><creationdate>20250106</creationdate><title>Fluorous-Phase- and Chiral-Axis-Enhanced Fluorescent Sensitivity and Chemoselectivity for Cysteine Recognition</title><author>Yang, Jiaqiao ; Qian, Cheng ; Su, Hanyu ; Zhang, Ji ; Yu, Shanshan ; Yu, Xiaoqi ; Pu, Lin</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c1811-158fbdbe84cd759b64ae82c2e8efc05eefba2cd5d9018c82a20e554f86587ca73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2025</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yang, Jiaqiao</creatorcontrib><creatorcontrib>Qian, Cheng</creatorcontrib><creatorcontrib>Su, Hanyu</creatorcontrib><creatorcontrib>Zhang, Ji</creatorcontrib><creatorcontrib>Yu, Shanshan</creatorcontrib><creatorcontrib>Yu, Xiaoqi</creatorcontrib><creatorcontrib>Pu, Lin</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yang, Jiaqiao</au><au>Qian, Cheng</au><au>Su, Hanyu</au><au>Zhang, Ji</au><au>Yu, Shanshan</au><au>Yu, Xiaoqi</au><au>Pu, Lin</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Fluorous-Phase- and Chiral-Axis-Enhanced Fluorescent Sensitivity and Chemoselectivity for Cysteine Recognition</atitle><jtitle>Organic letters</jtitle><addtitle>Org Lett</addtitle><date>2025-01-06</date><risdate>2025</risdate><issn>1523-7060</issn><issn>1523-7052</issn><eissn>1523-7052</eissn><abstract>Highly fluorinated naphthyl aldehyde
and binaphthyl aldehyde (
)-
were designed and synthesized for fluorous-phase-based sensing. Greatly enhanced sensitivity and chemoselectivity in going from
to (
)-
in the fluorescent detection of cysteine has been discovered. This is attributed to the increased structural rigidity of the axially chiral binaphthyl unit in (
)-
upon reaction with cysteine to form the corresponding thiazolidine product. The fluorous-phase-based detection of cysteine not only can allow the analysis to be conducted in a phase away from the interference of other organic and inorganic species but also results in significantly increased fluorescence response.</abstract><cop>United States</cop><pmid>39761029</pmid><doi>10.1021/acs.orglett.4c04175</doi><orcidid>https://orcid.org/0000-0003-1719-6137</orcidid><orcidid>https://orcid.org/0000-0002-5190-5905</orcidid><orcidid>https://orcid.org/0000-0001-8698-3228</orcidid><orcidid>https://orcid.org/0000-0002-2238-5824</orcidid><oa>free_for_read</oa></addata></record> |
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| recordid | cdi_proquest_miscellaneous_3151880652 |
| source | ACS Publications |
| title | Fluorous-Phase- and Chiral-Axis-Enhanced Fluorescent Sensitivity and Chemoselectivity for Cysteine Recognition |
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