Radical-mediated thiol-ene 'click' reactions in deep eutectic solvents for bioconjugation
Herein, we report the first application of deep eutectic solvents (DESs) in radical-mediated hydrothiolation reactions. Under UV and atmospheric-oxygen mediated conditions, the thiol-ene reaction was applied to amino acid and peptide ligation in DESs. The conditions facilitate highly-efficient synth...
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| Veröffentlicht in: | Green chemistry : an international journal and green chemistry resource : GC 2022-02, Vol.24 (4), p.1456-1462 |
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| container_title | Green chemistry : an international journal and green chemistry resource : GC |
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| creator | Nolan, Mark D Mezzetta, Andrea Guazzelli, Lorenzo Scanlan, Eoin M |
| description | Herein, we report the first application of deep eutectic solvents (DESs) in radical-mediated hydrothiolation reactions. Under UV and atmospheric-oxygen mediated conditions, the thiol-ene reaction was applied to amino acid and peptide ligation in DESs. The conditions facilitate highly-efficient synthesis of biomolecular targets using a 'green' methodology, with complete recycling of the reaction medium. Fluorescent labelling and glycosylation of a minimal sequence mimetic of angiotensin-converting enzyme 2 capable of binding the SARS-CoV-2 spike protein is demonstrated for applications in the study of inhibition of COVID-19 infectivity.
Herein, we report the first application of deep eutectic solvents (DESs) in radical-mediated hydrothiolation reactions. |
| doi_str_mv | 10.1039/d1gc03714e |
| format | Article |
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Herein, we report the first application of deep eutectic solvents (DESs) in radical-mediated hydrothiolation reactions.</description><subject>ACE2</subject><subject>Amino acids</subject><subject>Angiotensin</subject><subject>Angiotensin-converting enzyme 2</subject><subject>COVID-19</subject><subject>Eutectic reactions</subject><subject>Fluorescence</subject><subject>Glycosylation</subject><subject>Green chemistry</subject><subject>Infectivity</subject><subject>Labeling</subject><subject>Peptidyl-dipeptidase A</subject><subject>Severe acute respiratory syndrome coronavirus 2</subject><subject>Solvents</subject><subject>Spike protein</subject><issn>1463-9262</issn><issn>1463-9270</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNpF0E1LAzEQBuAgCtbqxbsQ8FAQVmeaNNkcpdYqFATRg6clm4-6dbupya7gv3drpZ5mGB7egZeQc4RrBKZuLC4NMIncHZABcsEyNZZwuN_F-JicpLQCQJSCD8jbs7aV0XW2drbSrbO0fa9CnbnG0ZGpK_MxotFp01ahSbRqqHVuQ13Xuv5kaAr1l2vaRH2ItKyCCc2qW-qtPiVHXtfJnf3NIXm9n71MH7LF0_xxervIDEPZZqWWwoBghltuS-UNTrxiCgWHHLhRTPpS6TL3kxwE2rzkOUiQOcAEvcKSDcnlLncTw2fnUlusQheb_mUxFgwUz3GsenW1UyaGlKLzxSZWax2_C4RiW11xh_Ppb3WzHl_scExm7_6rZT-nGGpD</recordid><startdate>20220221</startdate><enddate>20220221</enddate><creator>Nolan, Mark D</creator><creator>Mezzetta, Andrea</creator><creator>Guazzelli, Lorenzo</creator><creator>Scanlan, Eoin M</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7ST</scope><scope>7U6</scope><scope>8BQ</scope><scope>8FD</scope><scope>C1K</scope><scope>JG9</scope><orcidid>https://orcid.org/0000-0003-4655-2946</orcidid><orcidid>https://orcid.org/0000-0001-5176-2310</orcidid><orcidid>https://orcid.org/0000-0003-0385-5752</orcidid><orcidid>https://orcid.org/0000-0002-4540-9948</orcidid></search><sort><creationdate>20220221</creationdate><title>Radical-mediated thiol-ene 'click' reactions in deep eutectic solvents for bioconjugation</title><author>Nolan, Mark D ; Mezzetta, Andrea ; Guazzelli, Lorenzo ; Scanlan, Eoin M</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c317t-ba76c063c4d4db9fc15f9391640804c937fb9ab8f58061d8b48070780051f91b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>ACE2</topic><topic>Amino acids</topic><topic>Angiotensin</topic><topic>Angiotensin-converting enzyme 2</topic><topic>COVID-19</topic><topic>Eutectic reactions</topic><topic>Fluorescence</topic><topic>Glycosylation</topic><topic>Green chemistry</topic><topic>Infectivity</topic><topic>Labeling</topic><topic>Peptidyl-dipeptidase A</topic><topic>Severe acute respiratory syndrome coronavirus 2</topic><topic>Solvents</topic><topic>Spike protein</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Nolan, Mark D</creatorcontrib><creatorcontrib>Mezzetta, Andrea</creatorcontrib><creatorcontrib>Guazzelli, Lorenzo</creatorcontrib><creatorcontrib>Scanlan, Eoin M</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Environment Abstracts</collection><collection>Sustainability Science Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Materials Research Database</collection><jtitle>Green chemistry : an international journal and green chemistry resource : GC</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Nolan, Mark D</au><au>Mezzetta, Andrea</au><au>Guazzelli, Lorenzo</au><au>Scanlan, Eoin M</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Radical-mediated thiol-ene 'click' reactions in deep eutectic solvents for bioconjugation</atitle><jtitle>Green chemistry : an international journal and green chemistry resource : GC</jtitle><date>2022-02-21</date><risdate>2022</risdate><volume>24</volume><issue>4</issue><spage>1456</spage><epage>1462</epage><pages>1456-1462</pages><issn>1463-9262</issn><eissn>1463-9270</eissn><abstract>Herein, we report the first application of deep eutectic solvents (DESs) in radical-mediated hydrothiolation reactions. Under UV and atmospheric-oxygen mediated conditions, the thiol-ene reaction was applied to amino acid and peptide ligation in DESs. The conditions facilitate highly-efficient synthesis of biomolecular targets using a 'green' methodology, with complete recycling of the reaction medium. Fluorescent labelling and glycosylation of a minimal sequence mimetic of angiotensin-converting enzyme 2 capable of binding the SARS-CoV-2 spike protein is demonstrated for applications in the study of inhibition of COVID-19 infectivity.
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| identifier | ISSN: 1463-9262 |
| ispartof | Green chemistry : an international journal and green chemistry resource : GC, 2022-02, Vol.24 (4), p.1456-1462 |
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| language | eng |
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| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | ACE2 Amino acids Angiotensin Angiotensin-converting enzyme 2 COVID-19 Eutectic reactions Fluorescence Glycosylation Green chemistry Infectivity Labeling Peptidyl-dipeptidase A Severe acute respiratory syndrome coronavirus 2 Solvents Spike protein |
| title | Radical-mediated thiol-ene 'click' reactions in deep eutectic solvents for bioconjugation |
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