Synthesis and disulfide structure determination of porcine endothelin: an endothelium-derived vasoconstricting peptide
All disulfide analogs (types A, B and C) of porcine or human endothelin, a 21‐amino acid peptide having two intramolecular disulfide bonds, were synthesized and their retention times on HPLC were compared with that of natural endothelin. One of the analogs (type A) having disulfide bonds between pos...
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| Veröffentlicht in: | International Journal of Peptide and Protein Research 1988-12, Vol.32 (6), p.519-526 |
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| creator | KUMAGAYE, SHIN-ICHIROH KURODA, HISAYA NAKAJIMA, KIICHIRO WATANABE, TAKUSHI X. KIMURA, TERUTOSHI MASAKI, TOMOH SAKAKIBARA, SHUMPEI |
| description | All disulfide analogs (types A, B and C) of porcine or human endothelin, a 21‐amino acid peptide having two intramolecular disulfide bonds, were synthesized and their retention times on HPLC were compared with that of natural endothelin. One of the analogs (type A) having disulfide bonds between positions 1 and 15 and between 3 and 11 was found to be identical with natural endothelin. Random oxidation of fully reduced endothelin formed a mixture of type A and B in a ratio of 3:1, with almost none of type C, which has disulfide bonds between positions 1 and 3 and between 11 and 15. Type A endothelin was also synthesized by the segment condensation procedure in solution applying our maximum protection strategy. This product was found to have full vasoconstricting activity in rat pulmonary artery ring preparations; the potency was as high as that of the natural product. |
| doi_str_mv | 10.1111/j.1399-3011.1988.tb01383.x |
| format | Article |
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One of the analogs (type A) having disulfide bonds between positions 1 and 15 and between 3 and 11 was found to be identical with natural endothelin. Random oxidation of fully reduced endothelin formed a mixture of type A and B in a ratio of 3:1, with almost none of type C, which has disulfide bonds between positions 1 and 3 and between 11 and 15. Type A endothelin was also synthesized by the segment condensation procedure in solution applying our maximum protection strategy. This product was found to have full vasoconstricting activity in rat pulmonary artery ring preparations; the potency was as high as that of the natural product.</description><identifier>ISSN: 0367-8377</identifier><identifier>EISSN: 1399-3011</identifier><identifier>DOI: 10.1111/j.1399-3011.1988.tb01383.x</identifier><identifier>PMID: 3073147</identifier><identifier>CODEN: IJPPC3</identifier><language>eng</language><publisher>Oxford, UK: Blackwell Publishing Ltd</publisher><subject>Amino Acid Sequence ; Animals ; aortic endothelial cells ; Chemistry ; Chromatography, High Pressure Liquid ; disulfide analogs ; disulfide structure ; Disulfides - analysis ; endothelin ; Endothelins ; Endothelium, Vascular - physiology ; Exact sciences and technology ; In Vitro Techniques ; Indicators and Reagents ; Male ; Muscle, Smooth, Vascular - drug effects ; Muscle, Smooth, Vascular - physiology ; Organic chemistry ; Peptides ; Peptides - chemical synthesis ; Preparations and properties ; Pulmonary Artery - drug effects ; Pulmonary Artery - physiology ; Rats ; Rats, Inbred Strains ; solid phase synthesis ; solution synthesis ; Swine ; vasoconstricting activity ; Vasoconstriction</subject><ispartof>International Journal of Peptide and Protein Research, 1988-12, Vol.32 (6), p.519-526</ispartof><rights>1990 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5039-1919e2a9790d35ecb7844c6cf0f28aee63b3af160fbd5f596fb37da11854acf23</citedby><cites>FETCH-LOGICAL-c5039-1919e2a9790d35ecb7844c6cf0f28aee63b3af160fbd5f596fb37da11854acf23</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1111%2Fj.1399-3011.1988.tb01383.x$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1111%2Fj.1399-3011.1988.tb01383.x$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27903,27904,45553,45554</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=6695411$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/3073147$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>KUMAGAYE, SHIN-ICHIROH</creatorcontrib><creatorcontrib>KURODA, HISAYA</creatorcontrib><creatorcontrib>NAKAJIMA, KIICHIRO</creatorcontrib><creatorcontrib>WATANABE, TAKUSHI X.</creatorcontrib><creatorcontrib>KIMURA, TERUTOSHI</creatorcontrib><creatorcontrib>MASAKI, TOMOH</creatorcontrib><creatorcontrib>SAKAKIBARA, SHUMPEI</creatorcontrib><title>Synthesis and disulfide structure determination of porcine endothelin: an endothelium-derived vasoconstricting peptide</title><title>International Journal of Peptide and Protein Research</title><addtitle>Int J Pept Protein Res</addtitle><description>All disulfide analogs (types A, B and C) of porcine or human endothelin, a 21‐amino acid peptide having two intramolecular disulfide bonds, were synthesized and their retention times on HPLC were compared with that of natural endothelin. One of the analogs (type A) having disulfide bonds between positions 1 and 15 and between 3 and 11 was found to be identical with natural endothelin. Random oxidation of fully reduced endothelin formed a mixture of type A and B in a ratio of 3:1, with almost none of type C, which has disulfide bonds between positions 1 and 3 and between 11 and 15. Type A endothelin was also synthesized by the segment condensation procedure in solution applying our maximum protection strategy. This product was found to have full vasoconstricting activity in rat pulmonary artery ring preparations; the potency was as high as that of the natural product.</description><subject>Amino Acid Sequence</subject><subject>Animals</subject><subject>aortic endothelial cells</subject><subject>Chemistry</subject><subject>Chromatography, High Pressure Liquid</subject><subject>disulfide analogs</subject><subject>disulfide structure</subject><subject>Disulfides - analysis</subject><subject>endothelin</subject><subject>Endothelins</subject><subject>Endothelium, Vascular - physiology</subject><subject>Exact sciences and technology</subject><subject>In Vitro Techniques</subject><subject>Indicators and Reagents</subject><subject>Male</subject><subject>Muscle, Smooth, Vascular - drug effects</subject><subject>Muscle, Smooth, Vascular - physiology</subject><subject>Organic chemistry</subject><subject>Peptides</subject><subject>Peptides - chemical synthesis</subject><subject>Preparations and properties</subject><subject>Pulmonary Artery - drug effects</subject><subject>Pulmonary Artery - physiology</subject><subject>Rats</subject><subject>Rats, Inbred Strains</subject><subject>solid phase synthesis</subject><subject>solution synthesis</subject><subject>Swine</subject><subject>vasoconstricting activity</subject><subject>Vasoconstriction</subject><issn>0367-8377</issn><issn>1399-3011</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1988</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqVkF2P1CAUhonRrOPqTzBpjPGuFUpbyt4YnXV3TTZrNn5dEgoHZWxpBTrO_PtlMs14LTeEnPd9DnkQekVwQdJ5uykI5TynmJCC8LYtYocJbWmxe4RWp9FjtMK0YXlLGXuKnoWwwZhWlJVn6IxiRknFVmj7Ze_iLwg2ZNLpTNsw98ZqyEL0s4qzh0xDBD9YJ6MdXTaabBq9sg4ycHpM3d66i1T-95yHXIO3W9DZVoZRjS7BrIrW_cwmmGLCP0dPjOwDvFjuc_Tt6uPX9U1--_n60_r9ba5qTHlOOOFQSs441rQG1bG2qlSjDDZlKwEa2lFpSINNp2tT88Z0lGlJSFtXUpmSnqM3R-7kxz8zhCgGGxT0vXQwzkGwltEKsyoFL45B5ccQPBgxeTtIvxcEi4N0sREHs-JgVhyki0W62KXyy2XL3A2gT9XFcpq_XuYyKNkbL52y4RRrGl5XhKTYu2Psr-1h_x8fEOsPl5c14YmQHwk2RNidCNL_Fg2jrBY_7q7F3f39uinbG_GdPgBOL7Gs</recordid><startdate>198812</startdate><enddate>198812</enddate><creator>KUMAGAYE, SHIN-ICHIROH</creator><creator>KURODA, HISAYA</creator><creator>NAKAJIMA, KIICHIRO</creator><creator>WATANABE, TAKUSHI X.</creator><creator>KIMURA, TERUTOSHI</creator><creator>MASAKI, TOMOH</creator><creator>SAKAKIBARA, SHUMPEI</creator><general>Blackwell Publishing Ltd</general><general>Munksgaard</general><scope>BSCLL</scope><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>7X8</scope></search><sort><creationdate>198812</creationdate><title>Synthesis and disulfide structure determination of porcine endothelin: an endothelium-derived vasoconstricting peptide</title><author>KUMAGAYE, SHIN-ICHIROH ; KURODA, HISAYA ; NAKAJIMA, KIICHIRO ; WATANABE, TAKUSHI X. ; KIMURA, TERUTOSHI ; MASAKI, TOMOH ; SAKAKIBARA, SHUMPEI</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5039-1919e2a9790d35ecb7844c6cf0f28aee63b3af160fbd5f596fb37da11854acf23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1988</creationdate><topic>Amino Acid Sequence</topic><topic>Animals</topic><topic>aortic endothelial cells</topic><topic>Chemistry</topic><topic>Chromatography, High Pressure Liquid</topic><topic>disulfide analogs</topic><topic>disulfide structure</topic><topic>Disulfides - analysis</topic><topic>endothelin</topic><topic>Endothelins</topic><topic>Endothelium, Vascular - physiology</topic><topic>Exact sciences and technology</topic><topic>In Vitro Techniques</topic><topic>Indicators and Reagents</topic><topic>Male</topic><topic>Muscle, Smooth, Vascular - drug effects</topic><topic>Muscle, Smooth, Vascular - physiology</topic><topic>Organic chemistry</topic><topic>Peptides</topic><topic>Peptides - chemical synthesis</topic><topic>Preparations and properties</topic><topic>Pulmonary Artery - drug effects</topic><topic>Pulmonary Artery - physiology</topic><topic>Rats</topic><topic>Rats, Inbred Strains</topic><topic>solid phase synthesis</topic><topic>solution synthesis</topic><topic>Swine</topic><topic>vasoconstricting activity</topic><topic>Vasoconstriction</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>KUMAGAYE, SHIN-ICHIROH</creatorcontrib><creatorcontrib>KURODA, HISAYA</creatorcontrib><creatorcontrib>NAKAJIMA, KIICHIRO</creatorcontrib><creatorcontrib>WATANABE, TAKUSHI X.</creatorcontrib><creatorcontrib>KIMURA, TERUTOSHI</creatorcontrib><creatorcontrib>MASAKI, TOMOH</creatorcontrib><creatorcontrib>SAKAKIBARA, SHUMPEI</creatorcontrib><collection>Istex</collection><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>MEDLINE - Academic</collection><jtitle>International Journal of Peptide and Protein Research</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>KUMAGAYE, SHIN-ICHIROH</au><au>KURODA, HISAYA</au><au>NAKAJIMA, KIICHIRO</au><au>WATANABE, TAKUSHI X.</au><au>KIMURA, TERUTOSHI</au><au>MASAKI, TOMOH</au><au>SAKAKIBARA, SHUMPEI</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and disulfide structure determination of porcine endothelin: an endothelium-derived vasoconstricting peptide</atitle><jtitle>International Journal of Peptide and Protein Research</jtitle><addtitle>Int J Pept Protein Res</addtitle><date>1988-12</date><risdate>1988</risdate><volume>32</volume><issue>6</issue><spage>519</spage><epage>526</epage><pages>519-526</pages><issn>0367-8377</issn><eissn>1399-3011</eissn><coden>IJPPC3</coden><abstract>All disulfide analogs (types A, B and C) of porcine or human endothelin, a 21‐amino acid peptide having two intramolecular disulfide bonds, were synthesized and their retention times on HPLC were compared with that of natural endothelin. One of the analogs (type A) having disulfide bonds between positions 1 and 15 and between 3 and 11 was found to be identical with natural endothelin. Random oxidation of fully reduced endothelin formed a mixture of type A and B in a ratio of 3:1, with almost none of type C, which has disulfide bonds between positions 1 and 3 and between 11 and 15. Type A endothelin was also synthesized by the segment condensation procedure in solution applying our maximum protection strategy. This product was found to have full vasoconstricting activity in rat pulmonary artery ring preparations; the potency was as high as that of the natural product.</abstract><cop>Oxford, UK</cop><pub>Blackwell Publishing Ltd</pub><pmid>3073147</pmid><doi>10.1111/j.1399-3011.1988.tb01383.x</doi><tpages>8</tpages></addata></record> |
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| ispartof | International Journal of Peptide and Protein Research, 1988-12, Vol.32 (6), p.519-526 |
| issn | 0367-8377 1399-3011 |
| language | eng |
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| source | MEDLINE; Wiley Online Library Journals Frontfile Complete |
| subjects | Amino Acid Sequence Animals aortic endothelial cells Chemistry Chromatography, High Pressure Liquid disulfide analogs disulfide structure Disulfides - analysis endothelin Endothelins Endothelium, Vascular - physiology Exact sciences and technology In Vitro Techniques Indicators and Reagents Male Muscle, Smooth, Vascular - drug effects Muscle, Smooth, Vascular - physiology Organic chemistry Peptides Peptides - chemical synthesis Preparations and properties Pulmonary Artery - drug effects Pulmonary Artery - physiology Rats Rats, Inbred Strains solid phase synthesis solution synthesis Swine vasoconstricting activity Vasoconstriction |
| title | Synthesis and disulfide structure determination of porcine endothelin: an endothelium-derived vasoconstricting peptide |
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