Chemical synthesis of disulfide surrogate peptides by using beta-carbon dimethyl modified diaminodiacids
The replacement of disulfide bridges with metabolically stable isosteres is a promising strategy to improve the stability of disulfide-rich polypeptides towards reducing agents and isomerases. A diaminodiacid-based strategy is one of the most effective methods to construct disulfide bond mimics, but...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2021-10, Vol.19 (41), p.921-925 |
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| container_title | Organic & biomolecular chemistry |
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| creator | Cui, Ji-Bin Wei, Xiao-Xiong Zhao, Rui Zhu, Huixia Shi, Jing Bierer, Donald Li, Yi-Ming |
| description | The replacement of disulfide bridges with metabolically stable isosteres is a promising strategy to improve the stability of disulfide-rich polypeptides towards reducing agents and isomerases. A diaminodiacid-based strategy is one of the most effective methods to construct disulfide bond mimics, but modified diaminodiacids have not been developed till now. Inspired by the fact that alkylation of disulfide bonds can regulate the activity of polypeptides, herein, we report the first example of thioether bridged diaminodiacids incorporating Cys C
β
dimethyl modification, obtained by penicillamine (Pen)-based thiol alkylation. The utility of these new diaminodiacids was demonstrated by the synthesis of disulfide surrogates of oxytocin containing a short-span disulfide bond and of KIIIA with large-span disulfide bonds. This new type of synthetic bridge further extends the diaminodiacid toolbox to facilitate the study of the structure-activity relationship of disulfide-rich peptides.
We report the first example of thioether bridged diaminodiacids incorporating Cys C
β
dimethyl modification. |
| doi_str_mv | 10.1039/d1ob01715b |
| format | Article |
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β
dimethyl modification, obtained by penicillamine (Pen)-based thiol alkylation. The utility of these new diaminodiacids was demonstrated by the synthesis of disulfide surrogates of oxytocin containing a short-span disulfide bond and of KIIIA with large-span disulfide bonds. This new type of synthetic bridge further extends the diaminodiacid toolbox to facilitate the study of the structure-activity relationship of disulfide-rich peptides.
We report the first example of thioether bridged diaminodiacids incorporating Cys C
β
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β
dimethyl modification, obtained by penicillamine (Pen)-based thiol alkylation. The utility of these new diaminodiacids was demonstrated by the synthesis of disulfide surrogates of oxytocin containing a short-span disulfide bond and of KIIIA with large-span disulfide bonds. This new type of synthetic bridge further extends the diaminodiacid toolbox to facilitate the study of the structure-activity relationship of disulfide-rich peptides.
We report the first example of thioether bridged diaminodiacids incorporating Cys C
β
dimethyl modification.</description><subject>Alkylation</subject><subject>Chemical bonds</subject><subject>Chemical synthesis</subject><subject>Disulfide bonds</subject><subject>Oxytocin</subject><subject>Peptides</subject><subject>Polypeptides</subject><subject>Reducing agents</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNpdkctLxDAQxoMovi_elYAXEapJ0yabo65PWNiLnkuebqRt1kx72P_e6OoK5jIz3_xmGL4gdELJFSVMXlsaNaGC1noL7dNKiILUTG5v8pLsoQOAd0KoFLzaRXus4pRyWe6jxXThumBUi2HVDwsHAXD02AYYWx-swzCmFN_U4PDSLYesANYrPELo37B2gyqMSjr2eaJzw2LV4i7a4IOzWVFd6HOlTLBwhHa8asEd_8RD9Ppw_zJ9Kmbzx-fpzawwjImhYIppT72WtfRGldxmuabESya40HpSeW5MRdnE5udLNakrQyprHfHCGknZIbpY712m-DE6GJougHFtq3oXR2jKWkheSspZRs__oe9xTH2-LlMTzgSp6i_qck2ZFAGS880yhU6lVUNJ8-V_c0fnt9_-32b47GflqDtnN-iv4Rk4XQMJzKb794HsE0ski8M</recordid><startdate>20211027</startdate><enddate>20211027</enddate><creator>Cui, Ji-Bin</creator><creator>Wei, Xiao-Xiong</creator><creator>Zhao, Rui</creator><creator>Zhu, Huixia</creator><creator>Shi, Jing</creator><creator>Bierer, Donald</creator><creator>Li, Yi-Ming</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7T7</scope><scope>7TM</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-6716-8199</orcidid><orcidid>https://orcid.org/0000-0003-0180-4265</orcidid></search><sort><creationdate>20211027</creationdate><title>Chemical synthesis of disulfide surrogate peptides by using beta-carbon dimethyl modified diaminodiacids</title><author>Cui, Ji-Bin ; Wei, Xiao-Xiong ; Zhao, Rui ; Zhu, Huixia ; Shi, Jing ; Bierer, Donald ; Li, Yi-Ming</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c337t-3a3bf1fb959fca26dc33510f93767bb84f6cc4138ddddf2a854c04dde0f7dc913</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Alkylation</topic><topic>Chemical bonds</topic><topic>Chemical synthesis</topic><topic>Disulfide bonds</topic><topic>Oxytocin</topic><topic>Peptides</topic><topic>Polypeptides</topic><topic>Reducing agents</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Cui, Ji-Bin</creatorcontrib><creatorcontrib>Wei, Xiao-Xiong</creatorcontrib><creatorcontrib>Zhao, Rui</creatorcontrib><creatorcontrib>Zhu, Huixia</creatorcontrib><creatorcontrib>Shi, Jing</creatorcontrib><creatorcontrib>Bierer, Donald</creatorcontrib><creatorcontrib>Li, Yi-Ming</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Nucleic Acids Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Organic & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Cui, Ji-Bin</au><au>Wei, Xiao-Xiong</au><au>Zhao, Rui</au><au>Zhu, Huixia</au><au>Shi, Jing</au><au>Bierer, Donald</au><au>Li, Yi-Ming</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Chemical synthesis of disulfide surrogate peptides by using beta-carbon dimethyl modified diaminodiacids</atitle><jtitle>Organic & biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2021-10-27</date><risdate>2021</risdate><volume>19</volume><issue>41</issue><spage>921</spage><epage>925</epage><pages>921-925</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>The replacement of disulfide bridges with metabolically stable isosteres is a promising strategy to improve the stability of disulfide-rich polypeptides towards reducing agents and isomerases. A diaminodiacid-based strategy is one of the most effective methods to construct disulfide bond mimics, but modified diaminodiacids have not been developed till now. Inspired by the fact that alkylation of disulfide bonds can regulate the activity of polypeptides, herein, we report the first example of thioether bridged diaminodiacids incorporating Cys C
β
dimethyl modification, obtained by penicillamine (Pen)-based thiol alkylation. The utility of these new diaminodiacids was demonstrated by the synthesis of disulfide surrogates of oxytocin containing a short-span disulfide bond and of KIIIA with large-span disulfide bonds. This new type of synthetic bridge further extends the diaminodiacid toolbox to facilitate the study of the structure-activity relationship of disulfide-rich peptides.
We report the first example of thioether bridged diaminodiacids incorporating Cys C
β
dimethyl modification.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>34611692</pmid><doi>10.1039/d1ob01715b</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0001-6716-8199</orcidid><orcidid>https://orcid.org/0000-0003-0180-4265</orcidid></addata></record> |
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| ispartof | Organic & biomolecular chemistry, 2021-10, Vol.19 (41), p.921-925 |
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| language | eng |
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| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Alkylation Chemical bonds Chemical synthesis Disulfide bonds Oxytocin Peptides Polypeptides Reducing agents |
| title | Chemical synthesis of disulfide surrogate peptides by using beta-carbon dimethyl modified diaminodiacids |
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