A water-soluble, monitorable peptide and protein crosslinking agent
A novel, freely water-soluble, heterobifunctional crosslinking reagent, N-maleimido-6-aminocaproyl ester of 1-hydroxy-2-nitro-4-benzenesulfonic acid (mal-sac-HNSA), was synthesized and used for conjugation of sulfhydryl (cysteine)-containing peptides to carrier proteins. Reaction with amino groups r...
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| Veröffentlicht in: | Analytical biochemistry 1987-08, Vol.164 (2), p.494-501 |
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| container_end_page | 501 |
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| container_issue | 2 |
| container_start_page | 494 |
| container_title | Analytical biochemistry |
| container_volume | 164 |
| creator | Aldwin, Lois Nitecki, Danute E. |
| description | A novel, freely water-soluble, heterobifunctional crosslinking reagent,
N-maleimido-6-aminocaproyl ester of 1-hydroxy-2-nitro-4-benzenesulfonic acid (mal-sac-HNSA), was synthesized and used for conjugation of sulfhydryl (cysteine)-containing peptides to carrier proteins. Reaction with amino groups releases the dianion phenolate, HNSA, which allows convenient spectrophotometric quantitation of the reaction in progress. Since mal-sac-HNSA is completely water soluble, its concentration can be adjusted to maximize the rate of amine reaction and to minimize hydrolysis. Conjugates of peptides to appropriate carriers have elicited peptide-specific antibody and did not elicit detectable antibody specific to the crosslink. |
| doi_str_mv | 10.1016/0003-2697(87)90524-0 |
| format | Article |
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N-maleimido-6-aminocaproyl ester of 1-hydroxy-2-nitro-4-benzenesulfonic acid (mal-sac-HNSA), was synthesized and used for conjugation of sulfhydryl (cysteine)-containing peptides to carrier proteins. Reaction with amino groups releases the dianion phenolate, HNSA, which allows convenient spectrophotometric quantitation of the reaction in progress. Since mal-sac-HNSA is completely water soluble, its concentration can be adjusted to maximize the rate of amine reaction and to minimize hydrolysis. Conjugates of peptides to appropriate carriers have elicited peptide-specific antibody and did not elicit detectable antibody specific to the crosslink.</description><identifier>ISSN: 0003-2697</identifier><identifier>EISSN: 1096-0309</identifier><identifier>DOI: 10.1016/0003-2697(87)90524-0</identifier><identifier>PMID: 3674396</identifier><identifier>CODEN: ANBCA2</identifier><language>eng</language><publisher>San Diego, CA: Elsevier Inc</publisher><subject>Antigenic determinants, haptens, artificial antigens ; Antigens ; Benzenesulfonates - chemical synthesis ; Biological and medical sciences ; Cross-Linking Reagents - chemical synthesis ; crosslinking reagent ; Fundamental and applied biological sciences. Psychology ; Fundamental immunology ; heterobifunctional reagent ; immunochemical methods ; immunogen ; Maleimides - chemical synthesis ; Molecular immunology ; peptideprotein conjugation ; Peptides ; Proteins ; Solubility ; Water</subject><ispartof>Analytical biochemistry, 1987-08, Vol.164 (2), p.494-501</ispartof><rights>1987</rights><rights>1988 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c332t-a3a16c895d8488be3242ec9a465c90b0da4e27c7400a7e156ab3f016434be7eb3</citedby><cites>FETCH-LOGICAL-c332t-a3a16c895d8488be3242ec9a465c90b0da4e27c7400a7e156ab3f016434be7eb3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/0003269787905240$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3536,27903,27904,65309</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=7767512$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/3674396$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Aldwin, Lois</creatorcontrib><creatorcontrib>Nitecki, Danute E.</creatorcontrib><title>A water-soluble, monitorable peptide and protein crosslinking agent</title><title>Analytical biochemistry</title><addtitle>Anal Biochem</addtitle><description>A novel, freely water-soluble, heterobifunctional crosslinking reagent,
N-maleimido-6-aminocaproyl ester of 1-hydroxy-2-nitro-4-benzenesulfonic acid (mal-sac-HNSA), was synthesized and used for conjugation of sulfhydryl (cysteine)-containing peptides to carrier proteins. Reaction with amino groups releases the dianion phenolate, HNSA, which allows convenient spectrophotometric quantitation of the reaction in progress. Since mal-sac-HNSA is completely water soluble, its concentration can be adjusted to maximize the rate of amine reaction and to minimize hydrolysis. Conjugates of peptides to appropriate carriers have elicited peptide-specific antibody and did not elicit detectable antibody specific to the crosslink.</description><subject>Antigenic determinants, haptens, artificial antigens</subject><subject>Antigens</subject><subject>Benzenesulfonates - chemical synthesis</subject><subject>Biological and medical sciences</subject><subject>Cross-Linking Reagents - chemical synthesis</subject><subject>crosslinking reagent</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Fundamental immunology</subject><subject>heterobifunctional reagent</subject><subject>immunochemical methods</subject><subject>immunogen</subject><subject>Maleimides - chemical synthesis</subject><subject>Molecular immunology</subject><subject>peptideprotein conjugation</subject><subject>Peptides</subject><subject>Proteins</subject><subject>Solubility</subject><subject>Water</subject><issn>0003-2697</issn><issn>1096-0309</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1987</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkE1LxDAQhoMouq7-A4UeRBSsTpo0aS6CLH7Bghc9hzSdlWg3XZNW8d-bdZc96mkY5plh3oeQIwqXFKi4AgCWF0LJs0qeKygLnsMWGVFQIgcGapuMNsge2Y_xDYBSXopdssuE5EyJEZncZF-mx5DHrh3qFi-yeedd3wWTmmyBi941mBnfZIvQ9eh8ZkMXY-v8u_OvmXlF3x-QnZlpIx6u65i83N0-Tx7y6dP94-RmmlvGij43zFBhK1U2Fa-qGlnBC7TKcFFaBTU0hmMhreQARiIthanZLAXljNcosWZjcrq6m175GDD2eu6ixbY1Hrsh6ipFrySU_4KUK5CqUAnkK_A3VMCZXgQ3N-FbU9BLyXppUC8N6krqX8ka0trx-v5Qz7HZLK2tpvnJem6iNe0sGG9d3GBSClnSImHXKwyTtE-HQUfr0FtsXEDb66Zzf__xA7t8l0s</recordid><startdate>19870801</startdate><enddate>19870801</enddate><creator>Aldwin, Lois</creator><creator>Nitecki, Danute E.</creator><general>Elsevier Inc</general><general>Elsevier</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QL</scope><scope>C1K</scope><scope>7X8</scope></search><sort><creationdate>19870801</creationdate><title>A water-soluble, monitorable peptide and protein crosslinking agent</title><author>Aldwin, Lois ; Nitecki, Danute E.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c332t-a3a16c895d8488be3242ec9a465c90b0da4e27c7400a7e156ab3f016434be7eb3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1987</creationdate><topic>Antigenic determinants, haptens, artificial antigens</topic><topic>Antigens</topic><topic>Benzenesulfonates - chemical synthesis</topic><topic>Biological and medical sciences</topic><topic>Cross-Linking Reagents - chemical synthesis</topic><topic>crosslinking reagent</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Fundamental immunology</topic><topic>heterobifunctional reagent</topic><topic>immunochemical methods</topic><topic>immunogen</topic><topic>Maleimides - chemical synthesis</topic><topic>Molecular immunology</topic><topic>peptideprotein conjugation</topic><topic>Peptides</topic><topic>Proteins</topic><topic>Solubility</topic><topic>Water</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Aldwin, Lois</creatorcontrib><creatorcontrib>Nitecki, Danute E.</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Bacteriology Abstracts (Microbiology B)</collection><collection>Environmental Sciences and Pollution Management</collection><collection>MEDLINE - Academic</collection><jtitle>Analytical biochemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Aldwin, Lois</au><au>Nitecki, Danute E.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A water-soluble, monitorable peptide and protein crosslinking agent</atitle><jtitle>Analytical biochemistry</jtitle><addtitle>Anal Biochem</addtitle><date>1987-08-01</date><risdate>1987</risdate><volume>164</volume><issue>2</issue><spage>494</spage><epage>501</epage><pages>494-501</pages><issn>0003-2697</issn><eissn>1096-0309</eissn><coden>ANBCA2</coden><abstract>A novel, freely water-soluble, heterobifunctional crosslinking reagent,
N-maleimido-6-aminocaproyl ester of 1-hydroxy-2-nitro-4-benzenesulfonic acid (mal-sac-HNSA), was synthesized and used for conjugation of sulfhydryl (cysteine)-containing peptides to carrier proteins. Reaction with amino groups releases the dianion phenolate, HNSA, which allows convenient spectrophotometric quantitation of the reaction in progress. Since mal-sac-HNSA is completely water soluble, its concentration can be adjusted to maximize the rate of amine reaction and to minimize hydrolysis. Conjugates of peptides to appropriate carriers have elicited peptide-specific antibody and did not elicit detectable antibody specific to the crosslink.</abstract><cop>San Diego, CA</cop><pub>Elsevier Inc</pub><pmid>3674396</pmid><doi>10.1016/0003-2697(87)90524-0</doi><tpages>8</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0003-2697 |
| ispartof | Analytical biochemistry, 1987-08, Vol.164 (2), p.494-501 |
| issn | 0003-2697 1096-0309 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_81098705 |
| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | Antigenic determinants, haptens, artificial antigens Antigens Benzenesulfonates - chemical synthesis Biological and medical sciences Cross-Linking Reagents - chemical synthesis crosslinking reagent Fundamental and applied biological sciences. Psychology Fundamental immunology heterobifunctional reagent immunochemical methods immunogen Maleimides - chemical synthesis Molecular immunology peptideprotein conjugation Peptides Proteins Solubility Water |
| title | A water-soluble, monitorable peptide and protein crosslinking agent |
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