Heterobifunctional cross-linking agents incorporating perfluorinated aryl azides
New heterobifunctional cross-linking reagents were developed that possess a photoactive tetrafluorinated phenyl azide as the photoactive terminus and a chemically reactive succinimidyl ester as the electrophilic terminus. These reagents, succinimidyl N-(4-azido-2,3,5,6-tetrafluorobenzoyl)tyrosinate...
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| Veröffentlicht in: | Bioconjugate chemistry 1990-11, Vol.1 (6), p.419-424 |
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| container_title | Bioconjugate chemistry |
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| creator | Crocker, Peter J Imai, Nobuyuki Rajagopalan, Krishnan Boggess, Michael A Kwiatkowski, Stefan Dwyer, Lori D Vanaman, Thomas C Watt, David S |
| description | New heterobifunctional cross-linking reagents were developed that possess a photoactive tetrafluorinated phenyl azide as the photoactive terminus and a chemically reactive succinimidyl ester as the electrophilic terminus. These reagents, succinimidyl N-(4-azido-2,3,5,6-tetrafluorobenzoyl)tyrosinate (9) and succinimidyl 2-(4-azido-2,3,5,6-tetrafluorophenyl)thiazole-4-carboxylate (15), were designed to possess either an 125I or 35S radiolabel, respectively. In a biochemical study, the latter reagent was coupled to Lys-75 of calmodulin (CaM), and the radioiodinated monoadduct was photochemically cross-linked, in a calcium-dependent manner, to the porcine erythrocyte plasma membrane Ca2+, Mg2(+)-ATPase. Densitometry scans of the gel indicated a reproducible 22% cross-linking of the CaM with one of the Ca2+,Mg2(+)-ATPase bands. Since the purification of the Ca2+,Mg2(+)-ATPase results in micelles having Ca2+,Mg2(+)-ATPase with its CaM binding site oriented both to the inside and outside of the micelle, the amount of Ca2+,Mg2(+)-ATPase available for cross-linking was reduced by approximately half, suggesting that the actual cross-linking efficiency was on the order of 40%. |
| doi_str_mv | 10.1021/bc00006a008 |
| format | Article |
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These reagents, succinimidyl N-(4-azido-2,3,5,6-tetrafluorobenzoyl)tyrosinate (9) and succinimidyl 2-(4-azido-2,3,5,6-tetrafluorophenyl)thiazole-4-carboxylate (15), were designed to possess either an 125I or 35S radiolabel, respectively. In a biochemical study, the latter reagent was coupled to Lys-75 of calmodulin (CaM), and the radioiodinated monoadduct was photochemically cross-linked, in a calcium-dependent manner, to the porcine erythrocyte plasma membrane Ca2+, Mg2(+)-ATPase. Densitometry scans of the gel indicated a reproducible 22% cross-linking of the CaM with one of the Ca2+,Mg2(+)-ATPase bands. Since the purification of the Ca2+,Mg2(+)-ATPase results in micelles having Ca2+,Mg2(+)-ATPase with its CaM binding site oriented both to the inside and outside of the micelle, the amount of Ca2+,Mg2(+)-ATPase available for cross-linking was reduced by approximately half, suggesting that the actual cross-linking efficiency was on the order of 40%.</description><identifier>ISSN: 1043-1802</identifier><identifier>EISSN: 1520-4812</identifier><identifier>DOI: 10.1021/bc00006a008</identifier><identifier>PMID: 2151563</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Animals ; Azides - chemical synthesis ; Azides - chemistry ; Ca(2+) Mg(2+)-ATPase - blood ; Ca(2+) Mg(2+)-ATPase - chemistry ; Calcium - pharmacology ; Calcium-Transporting ATPases - blood ; Calcium-Transporting ATPases - chemistry ; Calmodulin - chemistry ; Chemical Phenomena ; Chemistry ; Chromatography, High Pressure Liquid ; Cross-Linking Reagents - chemical synthesis ; Electrophoresis, Polyacrylamide Gel ; Erythrocyte Membrane - enzymology ; Molecular Structure ; Photochemistry ; Spectrophotometry, Ultraviolet ; Swine ; Thiazoles - chemical synthesis ; Tyrosine - analogs & derivatives ; Tyrosine - chemical synthesis ; Tyrosine - chemistry</subject><ispartof>Bioconjugate chemistry, 1990-11, Vol.1 (6), p.419-424</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a354t-805687a40bc12227e2ccf8b8b54f572dc6f6a633d4164d0bb7f39d00d0499d553</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/bc00006a008$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/bc00006a008$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/2151563$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Crocker, Peter J</creatorcontrib><creatorcontrib>Imai, Nobuyuki</creatorcontrib><creatorcontrib>Rajagopalan, Krishnan</creatorcontrib><creatorcontrib>Boggess, Michael A</creatorcontrib><creatorcontrib>Kwiatkowski, Stefan</creatorcontrib><creatorcontrib>Dwyer, Lori D</creatorcontrib><creatorcontrib>Vanaman, Thomas C</creatorcontrib><creatorcontrib>Watt, David S</creatorcontrib><title>Heterobifunctional cross-linking agents incorporating perfluorinated aryl azides</title><title>Bioconjugate chemistry</title><addtitle>Bioconjugate Chem</addtitle><description>New heterobifunctional cross-linking reagents were developed that possess a photoactive tetrafluorinated phenyl azide as the photoactive terminus and a chemically reactive succinimidyl ester as the electrophilic terminus. These reagents, succinimidyl N-(4-azido-2,3,5,6-tetrafluorobenzoyl)tyrosinate (9) and succinimidyl 2-(4-azido-2,3,5,6-tetrafluorophenyl)thiazole-4-carboxylate (15), were designed to possess either an 125I or 35S radiolabel, respectively. In a biochemical study, the latter reagent was coupled to Lys-75 of calmodulin (CaM), and the radioiodinated monoadduct was photochemically cross-linked, in a calcium-dependent manner, to the porcine erythrocyte plasma membrane Ca2+, Mg2(+)-ATPase. Densitometry scans of the gel indicated a reproducible 22% cross-linking of the CaM with one of the Ca2+,Mg2(+)-ATPase bands. Since the purification of the Ca2+,Mg2(+)-ATPase results in micelles having Ca2+,Mg2(+)-ATPase with its CaM binding site oriented both to the inside and outside of the micelle, the amount of Ca2+,Mg2(+)-ATPase available for cross-linking was reduced by approximately half, suggesting that the actual cross-linking efficiency was on the order of 40%.</description><subject>Animals</subject><subject>Azides - chemical synthesis</subject><subject>Azides - chemistry</subject><subject>Ca(2+) Mg(2+)-ATPase - blood</subject><subject>Ca(2+) Mg(2+)-ATPase - chemistry</subject><subject>Calcium - pharmacology</subject><subject>Calcium-Transporting ATPases - blood</subject><subject>Calcium-Transporting ATPases - chemistry</subject><subject>Calmodulin - chemistry</subject><subject>Chemical Phenomena</subject><subject>Chemistry</subject><subject>Chromatography, High Pressure Liquid</subject><subject>Cross-Linking Reagents - chemical synthesis</subject><subject>Electrophoresis, Polyacrylamide Gel</subject><subject>Erythrocyte Membrane - enzymology</subject><subject>Molecular Structure</subject><subject>Photochemistry</subject><subject>Spectrophotometry, Ultraviolet</subject><subject>Swine</subject><subject>Thiazoles - chemical synthesis</subject><subject>Tyrosine - analogs & derivatives</subject><subject>Tyrosine - chemical synthesis</subject><subject>Tyrosine - chemistry</subject><issn>1043-1802</issn><issn>1520-4812</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1990</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkMtLxDAQxoMovk-ehZ70INXJs-lRRF1RcGEVjyFNUol2mzVpQf3rje4iHpzLDPP9mMeH0AGGUwwEnzUGcggNINfQNuYESiYxWc81MFpiCWQL7aT0kqkaS7KJNgnmmAu6jaYTN7gYGt-OvRl86HVXmBhSKjvfv_r-udDPrh9S4XsT4iJEPXw3Fy623Rii7_XgbKHjR1foT29d2kMbre6S21_lXfR4dflwMSnv7q9vLs7vSk05G0oJXMhKM2gMJoRUjhjTykY2nLW8ItaIVmhBqWVYMAtNU7W0tgAWWF1bzukuOlrOXcTwNro0qLlPxnWd7l0Yk5JAK1YTlsGTJfjzVnStWkQ_zxcrDOrbP_XHv0wfrsaOzdzZX3ZlWNbLpe7T4N5_ZR1flahoxdXDdKbk0-1EyBkoyPzxktcmqZcwxmxw-nfzF-P9huA</recordid><startdate>19901101</startdate><enddate>19901101</enddate><creator>Crocker, Peter J</creator><creator>Imai, Nobuyuki</creator><creator>Rajagopalan, Krishnan</creator><creator>Boggess, Michael A</creator><creator>Kwiatkowski, Stefan</creator><creator>Dwyer, Lori D</creator><creator>Vanaman, Thomas C</creator><creator>Watt, David S</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><scope>7X8</scope></search><sort><creationdate>19901101</creationdate><title>Heterobifunctional cross-linking agents incorporating perfluorinated aryl azides</title><author>Crocker, Peter J ; Imai, Nobuyuki ; Rajagopalan, Krishnan ; Boggess, Michael A ; Kwiatkowski, Stefan ; Dwyer, Lori D ; Vanaman, Thomas C ; Watt, David S</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a354t-805687a40bc12227e2ccf8b8b54f572dc6f6a633d4164d0bb7f39d00d0499d553</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1990</creationdate><topic>Animals</topic><topic>Azides - chemical synthesis</topic><topic>Azides - chemistry</topic><topic>Ca(2+) Mg(2+)-ATPase - blood</topic><topic>Ca(2+) Mg(2+)-ATPase - chemistry</topic><topic>Calcium - pharmacology</topic><topic>Calcium-Transporting ATPases - blood</topic><topic>Calcium-Transporting ATPases - chemistry</topic><topic>Calmodulin - chemistry</topic><topic>Chemical Phenomena</topic><topic>Chemistry</topic><topic>Chromatography, High Pressure Liquid</topic><topic>Cross-Linking Reagents - chemical synthesis</topic><topic>Electrophoresis, Polyacrylamide Gel</topic><topic>Erythrocyte Membrane - enzymology</topic><topic>Molecular Structure</topic><topic>Photochemistry</topic><topic>Spectrophotometry, Ultraviolet</topic><topic>Swine</topic><topic>Thiazoles - chemical synthesis</topic><topic>Tyrosine - analogs & derivatives</topic><topic>Tyrosine - chemical synthesis</topic><topic>Tyrosine - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Crocker, Peter J</creatorcontrib><creatorcontrib>Imai, Nobuyuki</creatorcontrib><creatorcontrib>Rajagopalan, Krishnan</creatorcontrib><creatorcontrib>Boggess, Michael A</creatorcontrib><creatorcontrib>Kwiatkowski, Stefan</creatorcontrib><creatorcontrib>Dwyer, Lori D</creatorcontrib><creatorcontrib>Vanaman, Thomas C</creatorcontrib><creatorcontrib>Watt, David S</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><collection>MEDLINE - Academic</collection><jtitle>Bioconjugate chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Crocker, Peter J</au><au>Imai, Nobuyuki</au><au>Rajagopalan, Krishnan</au><au>Boggess, Michael A</au><au>Kwiatkowski, Stefan</au><au>Dwyer, Lori D</au><au>Vanaman, Thomas C</au><au>Watt, David S</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Heterobifunctional cross-linking agents incorporating perfluorinated aryl azides</atitle><jtitle>Bioconjugate chemistry</jtitle><addtitle>Bioconjugate Chem</addtitle><date>1990-11-01</date><risdate>1990</risdate><volume>1</volume><issue>6</issue><spage>419</spage><epage>424</epage><pages>419-424</pages><issn>1043-1802</issn><eissn>1520-4812</eissn><abstract>New heterobifunctional cross-linking reagents were developed that possess a photoactive tetrafluorinated phenyl azide as the photoactive terminus and a chemically reactive succinimidyl ester as the electrophilic terminus. These reagents, succinimidyl N-(4-azido-2,3,5,6-tetrafluorobenzoyl)tyrosinate (9) and succinimidyl 2-(4-azido-2,3,5,6-tetrafluorophenyl)thiazole-4-carboxylate (15), were designed to possess either an 125I or 35S radiolabel, respectively. In a biochemical study, the latter reagent was coupled to Lys-75 of calmodulin (CaM), and the radioiodinated monoadduct was photochemically cross-linked, in a calcium-dependent manner, to the porcine erythrocyte plasma membrane Ca2+, Mg2(+)-ATPase. Densitometry scans of the gel indicated a reproducible 22% cross-linking of the CaM with one of the Ca2+,Mg2(+)-ATPase bands. Since the purification of the Ca2+,Mg2(+)-ATPase results in micelles having Ca2+,Mg2(+)-ATPase with its CaM binding site oriented both to the inside and outside of the micelle, the amount of Ca2+,Mg2(+)-ATPase available for cross-linking was reduced by approximately half, suggesting that the actual cross-linking efficiency was on the order of 40%.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>2151563</pmid><doi>10.1021/bc00006a008</doi><tpages>6</tpages></addata></record> |
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| identifier | ISSN: 1043-1802 |
| ispartof | Bioconjugate chemistry, 1990-11, Vol.1 (6), p.419-424 |
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| source | ACS Publications; MEDLINE |
| subjects | Animals Azides - chemical synthesis Azides - chemistry Ca(2+) Mg(2+)-ATPase - blood Ca(2+) Mg(2+)-ATPase - chemistry Calcium - pharmacology Calcium-Transporting ATPases - blood Calcium-Transporting ATPases - chemistry Calmodulin - chemistry Chemical Phenomena Chemistry Chromatography, High Pressure Liquid Cross-Linking Reagents - chemical synthesis Electrophoresis, Polyacrylamide Gel Erythrocyte Membrane - enzymology Molecular Structure Photochemistry Spectrophotometry, Ultraviolet Swine Thiazoles - chemical synthesis Tyrosine - analogs & derivatives Tyrosine - chemical synthesis Tyrosine - chemistry |
| title | Heterobifunctional cross-linking agents incorporating perfluorinated aryl azides |
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