A Chemoselective Method for Site-Specific Immobilization of Peptides via Aminooxy Group
Site-specific modification of peptides and proteins is an important area of basic research for preparation of well-defined biosensors and probes. The unique properties of aminooxy group present an opportunity for chemoselective site-specific immobilization of peptides to prepare well-defined biosens...
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| Veröffentlicht in: | Bioconjugate chemistry 2001-03, Vol.12 (2), p.139-142 |
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| container_end_page | 142 |
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| container_title | Bioconjugate chemistry |
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| creator | Adamczyk, Maciej Gebler, John C Reddy, Rajarathnam E Yu, Zhiguang |
| description | Site-specific modification of peptides and proteins is an important area of basic research for preparation of well-defined biosensors and probes. The unique properties of aminooxy group present an opportunity for chemoselective site-specific immobilization of peptides to prepare well-defined biosensors. We have prepared FLAG peptide derivatives containing l-ε-aminooxylysine (l-ε-AOLys, 1a) and l-lysine units in their sequence at the C- and N-terminals via solid-phase synthesis. Site-specific modification of peptides through aminooxy group was demonstrated in the preparation of biosensors and selective conjugation in the preparation of biotinylated probes. Effect of the incorporation of l-ε-AOLys (1a) into the peptide sequence and its subsequent labeling on the FLAG epitopic character was measured using a surface plasmon resonance detector. It was found that incorporation of l-ε-AOLys (1a) into the FLAG peptide and site-specific immobilization through aminooxy group preserved the integrity of FLAG epitope. |
| doi_str_mv | 10.1021/bc0001239 |
| format | Article |
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The unique properties of aminooxy group present an opportunity for chemoselective site-specific immobilization of peptides to prepare well-defined biosensors. We have prepared FLAG peptide derivatives containing l-ε-aminooxylysine (l-ε-AOLys, 1a) and l-lysine units in their sequence at the C- and N-terminals via solid-phase synthesis. Site-specific modification of peptides through aminooxy group was demonstrated in the preparation of biosensors and selective conjugation in the preparation of biotinylated probes. Effect of the incorporation of l-ε-AOLys (1a) into the peptide sequence and its subsequent labeling on the FLAG epitopic character was measured using a surface plasmon resonance detector. It was found that incorporation of l-ε-AOLys (1a) into the FLAG peptide and site-specific immobilization through aminooxy group preserved the integrity of FLAG epitope.</description><identifier>ISSN: 1043-1802</identifier><identifier>EISSN: 1520-4812</identifier><identifier>DOI: 10.1021/bc0001239</identifier><identifier>PMID: 11312673</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Antibodies, Monoclonal - immunology ; Antibodies, Monoclonal - metabolism ; Biosensing Techniques ; Epitopes ; Hydrogen-Ion Concentration ; Lysine - analogs & derivatives ; Lysine - chemistry ; Mutagenesis, Site-Directed ; Oligopeptides ; Peptides - chemical synthesis ; Peptides - chemistry ; Peptides - immunology ; Peptides - metabolism ; Surface Plasmon Resonance</subject><ispartof>Bioconjugate chemistry, 2001-03, Vol.12 (2), p.139-142</ispartof><rights>Copyright © 2001 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a349t-b0d7e88693aebfd803988dbebc2ebd4541c156c391acd801dedfc9e127b678fa3</citedby><cites>FETCH-LOGICAL-a349t-b0d7e88693aebfd803988dbebc2ebd4541c156c391acd801dedfc9e127b678fa3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/bc0001239$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/bc0001239$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,777,781,2752,27057,27905,27906,56719,56769</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11312673$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Adamczyk, Maciej</creatorcontrib><creatorcontrib>Gebler, John C</creatorcontrib><creatorcontrib>Reddy, Rajarathnam E</creatorcontrib><creatorcontrib>Yu, Zhiguang</creatorcontrib><title>A Chemoselective Method for Site-Specific Immobilization of Peptides via Aminooxy Group</title><title>Bioconjugate chemistry</title><addtitle>Bioconjugate Chem</addtitle><description>Site-specific modification of peptides and proteins is an important area of basic research for preparation of well-defined biosensors and probes. The unique properties of aminooxy group present an opportunity for chemoselective site-specific immobilization of peptides to prepare well-defined biosensors. We have prepared FLAG peptide derivatives containing l-ε-aminooxylysine (l-ε-AOLys, 1a) and l-lysine units in their sequence at the C- and N-terminals via solid-phase synthesis. Site-specific modification of peptides through aminooxy group was demonstrated in the preparation of biosensors and selective conjugation in the preparation of biotinylated probes. Effect of the incorporation of l-ε-AOLys (1a) into the peptide sequence and its subsequent labeling on the FLAG epitopic character was measured using a surface plasmon resonance detector. It was found that incorporation of l-ε-AOLys (1a) into the FLAG peptide and site-specific immobilization through aminooxy group preserved the integrity of FLAG epitope.</description><subject>Antibodies, Monoclonal - immunology</subject><subject>Antibodies, Monoclonal - metabolism</subject><subject>Biosensing Techniques</subject><subject>Epitopes</subject><subject>Hydrogen-Ion Concentration</subject><subject>Lysine - analogs & derivatives</subject><subject>Lysine - chemistry</subject><subject>Mutagenesis, Site-Directed</subject><subject>Oligopeptides</subject><subject>Peptides - chemical synthesis</subject><subject>Peptides - chemistry</subject><subject>Peptides - immunology</subject><subject>Peptides - metabolism</subject><subject>Surface Plasmon Resonance</subject><issn>1043-1802</issn><issn>1520-4812</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2001</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0MtOwzAQBVALgXgv-AHkDQsWAY-dNM6yqqAg8WiVIpaWHxNhaOooTqvC1xPUCjasPNI9mpEvIWfAroBxuDaWMQZcFDvkEDLOklQC3-1nlooEJOMH5CjG9x4VIPk-OQAQwAe5OCSvQzp6wzpEnKPt_ArpI3ZvwdEqtLT0HSZlg9ZX3tL7ug7Gz_2X7nxY0FDRCTaddxjpyms6rP0ihPUnHbdh2ZyQvUrPI55u32PycnszG90lD8_j-9HwIdEiLbrEMJejlINCaDSVk0wUUjqDxnI0Ls1SsJANrChA2z4Fh66yBQLPzSCXlRbH5HKz17YhxhYr1bS-1u2nAqZ-ylG_5fT2fGObpanR_cltGz1INsDHDte_uW4_VB_nmZpNSvVUFmWayama9v5i47WN6j0s20X_1X8OfwNr4nq1</recordid><startdate>20010301</startdate><enddate>20010301</enddate><creator>Adamczyk, Maciej</creator><creator>Gebler, John C</creator><creator>Reddy, Rajarathnam E</creator><creator>Yu, Zhiguang</creator><general>American Chemical Society</general><scope>BSCLL</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></search><sort><creationdate>20010301</creationdate><title>A Chemoselective Method for Site-Specific Immobilization of Peptides via Aminooxy Group</title><author>Adamczyk, Maciej ; Gebler, John C ; Reddy, Rajarathnam E ; Yu, Zhiguang</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a349t-b0d7e88693aebfd803988dbebc2ebd4541c156c391acd801dedfc9e127b678fa3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2001</creationdate><topic>Antibodies, Monoclonal - immunology</topic><topic>Antibodies, Monoclonal - metabolism</topic><topic>Biosensing Techniques</topic><topic>Epitopes</topic><topic>Hydrogen-Ion Concentration</topic><topic>Lysine - analogs & derivatives</topic><topic>Lysine - chemistry</topic><topic>Mutagenesis, Site-Directed</topic><topic>Oligopeptides</topic><topic>Peptides - chemical synthesis</topic><topic>Peptides - chemistry</topic><topic>Peptides - immunology</topic><topic>Peptides - metabolism</topic><topic>Surface Plasmon Resonance</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Adamczyk, Maciej</creatorcontrib><creatorcontrib>Gebler, John C</creatorcontrib><creatorcontrib>Reddy, Rajarathnam E</creatorcontrib><creatorcontrib>Yu, Zhiguang</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><jtitle>Bioconjugate chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Adamczyk, Maciej</au><au>Gebler, John C</au><au>Reddy, Rajarathnam E</au><au>Yu, Zhiguang</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Chemoselective Method for Site-Specific Immobilization of Peptides via Aminooxy Group</atitle><jtitle>Bioconjugate chemistry</jtitle><addtitle>Bioconjugate Chem</addtitle><date>2001-03-01</date><risdate>2001</risdate><volume>12</volume><issue>2</issue><spage>139</spage><epage>142</epage><pages>139-142</pages><issn>1043-1802</issn><eissn>1520-4812</eissn><abstract>Site-specific modification of peptides and proteins is an important area of basic research for preparation of well-defined biosensors and probes. The unique properties of aminooxy group present an opportunity for chemoselective site-specific immobilization of peptides to prepare well-defined biosensors. We have prepared FLAG peptide derivatives containing l-ε-aminooxylysine (l-ε-AOLys, 1a) and l-lysine units in their sequence at the C- and N-terminals via solid-phase synthesis. Site-specific modification of peptides through aminooxy group was demonstrated in the preparation of biosensors and selective conjugation in the preparation of biotinylated probes. Effect of the incorporation of l-ε-AOLys (1a) into the peptide sequence and its subsequent labeling on the FLAG epitopic character was measured using a surface plasmon resonance detector. It was found that incorporation of l-ε-AOLys (1a) into the FLAG peptide and site-specific immobilization through aminooxy group preserved the integrity of FLAG epitope.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>11312673</pmid><doi>10.1021/bc0001239</doi><tpages>4</tpages></addata></record> |
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| identifier | ISSN: 1043-1802 |
| ispartof | Bioconjugate chemistry, 2001-03, Vol.12 (2), p.139-142 |
| issn | 1043-1802 1520-4812 |
| language | eng |
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| source | MEDLINE; ACS Publications |
| subjects | Antibodies, Monoclonal - immunology Antibodies, Monoclonal - metabolism Biosensing Techniques Epitopes Hydrogen-Ion Concentration Lysine - analogs & derivatives Lysine - chemistry Mutagenesis, Site-Directed Oligopeptides Peptides - chemical synthesis Peptides - chemistry Peptides - immunology Peptides - metabolism Surface Plasmon Resonance |
| title | A Chemoselective Method for Site-Specific Immobilization of Peptides via Aminooxy Group |
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