Synthesis of Salmon Endorphin
First synthesis of a nonacosapeptide corresponding to the entire amino acid sequence of salmon endorphin, Ac-Tyr-Gly-Gly-Phe-Met-Lys-Pro-Tyr-Thr-Lys-Gln-Ser-His-Lys-Pro-Leu-Ile-Thr-Leu-Leu-Lys-His-Ile-Thr-Leu-Lys-Asn-Glu-Gln-OH, and its des-acetyl derivative was described. Toward the synthesis of th...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 1980/05/25, Vol.28(5), pp.1655-1658 |
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| container_title | Chemical & pharmaceutical bulletin |
| container_volume | 28 |
| creator | FUJINO, MASAHIKO KITADA, CHIEKO WAKIMASU, MITSUHIRO NISHIMURA, OSAMU DOI, TAKAYUKI KAWAUCHI, HIROSHI MUNEKATA, EISUKE |
| description | First synthesis of a nonacosapeptide corresponding to the entire amino acid sequence of salmon endorphin, Ac-Tyr-Gly-Gly-Phe-Met-Lys-Pro-Tyr-Thr-Lys-Gln-Ser-His-Lys-Pro-Leu-Ile-Thr-Leu-Leu-Lys-His-Ile-Thr-Leu-Lys-Asn-Glu-Gln-OH, and its des-acetyl derivative was described. Toward the synthesis of this hormone, five fragments, 1-7, 8-15, 16-18, 19-24 and 25-29, were prepared and the fragments were served as the building blocks for the final construction of the entire amino acid sequence of the hormone. The final deprotection of the fully protected peptide was achieved by treatment with trifluoroacetic acid and the purification of the synthetic peptides was effected by a column chromatography on CM-cellulose and then Sephadex LH-20. The synthetic acetylated nonacosapeptide was compared with purified natural salmon endorphin by means of chromatography, electrophoresis and also enzymatic digestion and found to be indistinguishable from natural isolated salmon endorphin. The opiate activity of the synthetic salmon endorphin and des-acetyl salmon endorphin was also described. |
| doi_str_mv | 10.1248/cpb.28.1655 |
| format | Article |
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Toward the synthesis of this hormone, five fragments, 1-7, 8-15, 16-18, 19-24 and 25-29, were prepared and the fragments were served as the building blocks for the final construction of the entire amino acid sequence of the hormone. The final deprotection of the fully protected peptide was achieved by treatment with trifluoroacetic acid and the purification of the synthetic peptides was effected by a column chromatography on CM-cellulose and then Sephadex LH-20. The synthetic acetylated nonacosapeptide was compared with purified natural salmon endorphin by means of chromatography, electrophoresis and also enzymatic digestion and found to be indistinguishable from natural isolated salmon endorphin. The opiate activity of the synthetic salmon endorphin and des-acetyl salmon endorphin was also described.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.28.1655</identifier><identifier>PMID: 6250730</identifier><language>eng</language><publisher>Japan: The Pharmaceutical Society of Japan</publisher><subject>Animals ; Binding, Competitive ; DCC-HONB method ; Endorphins - chemical synthesis ; Endorphins - pharmacology ; In Vitro Techniques ; Receptors, Opioid - drug effects ; Salmon</subject><ispartof>Chemical and Pharmaceutical Bulletin, 1980/05/25, Vol.28(5), pp.1655-1658</ispartof><rights>The Pharmaceutical Society of Japan</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c549t-ab0a5fba18d6c3cdeddecd70f3f8b27b8031c34043d3fcefe483244e6a3007623</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,1881,27922,27923</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/6250730$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>FUJINO, MASAHIKO</creatorcontrib><creatorcontrib>KITADA, CHIEKO</creatorcontrib><creatorcontrib>WAKIMASU, MITSUHIRO</creatorcontrib><creatorcontrib>NISHIMURA, OSAMU</creatorcontrib><creatorcontrib>DOI, TAKAYUKI</creatorcontrib><creatorcontrib>KAWAUCHI, HIROSHI</creatorcontrib><creatorcontrib>MUNEKATA, EISUKE</creatorcontrib><title>Synthesis of Salmon Endorphin</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>First synthesis of a nonacosapeptide corresponding to the entire amino acid sequence of salmon endorphin, Ac-Tyr-Gly-Gly-Phe-Met-Lys-Pro-Tyr-Thr-Lys-Gln-Ser-His-Lys-Pro-Leu-Ile-Thr-Leu-Leu-Lys-His-Ile-Thr-Leu-Lys-Asn-Glu-Gln-OH, and its des-acetyl derivative was described. Toward the synthesis of this hormone, five fragments, 1-7, 8-15, 16-18, 19-24 and 25-29, were prepared and the fragments were served as the building blocks for the final construction of the entire amino acid sequence of the hormone. The final deprotection of the fully protected peptide was achieved by treatment with trifluoroacetic acid and the purification of the synthetic peptides was effected by a column chromatography on CM-cellulose and then Sephadex LH-20. The synthetic acetylated nonacosapeptide was compared with purified natural salmon endorphin by means of chromatography, electrophoresis and also enzymatic digestion and found to be indistinguishable from natural isolated salmon endorphin. The opiate activity of the synthetic salmon endorphin and des-acetyl salmon endorphin was also described.</description><subject>Animals</subject><subject>Binding, Competitive</subject><subject>DCC-HONB method</subject><subject>Endorphins - chemical synthesis</subject><subject>Endorphins - pharmacology</subject><subject>In Vitro Techniques</subject><subject>Receptors, Opioid - drug effects</subject><subject>Salmon</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1980</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpFkE1LAzEQhoMotVZPngs9eZGtk0yymx5F6wcUPFTPIZsPu2W_TLaH_nt3bamXmYHn5YF5CbmlMKeMywfT5nMm5zQV4oyMKfIsEYzhORkDwCJhmOIluYpxC8AEZDgio_TvgDGZrvd1t3GxiLPGz9a6rJp6tqxtE9pNUV-TC6_L6G6Oe0K-XpafT2_J6uP1_elxlRjBF12ic9DC55pKmxo01lnrjM3Ao5c5y3IJSA1y4GjRG-cdl8g4d6lGgCxlOCF3B28bmp-di52qimhcWeraNbuoMsGQS5b2wftD0IQmxuC8akNR6bBXFNRQhurLUEyqoYw-PT1qd3nl7Cl7_L7nzwe-jZ3-dieuQ1eY0g0uuhBy8InDGLT_eKODcjX-AmEicUA</recordid><startdate>19800101</startdate><enddate>19800101</enddate><creator>FUJINO, MASAHIKO</creator><creator>KITADA, CHIEKO</creator><creator>WAKIMASU, MITSUHIRO</creator><creator>NISHIMURA, OSAMU</creator><creator>DOI, TAKAYUKI</creator><creator>KAWAUCHI, HIROSHI</creator><creator>MUNEKATA, EISUKE</creator><general>The Pharmaceutical Society of Japan</general><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>19800101</creationdate><title>Synthesis of Salmon Endorphin</title><author>FUJINO, MASAHIKO ; KITADA, CHIEKO ; WAKIMASU, MITSUHIRO ; NISHIMURA, OSAMU ; DOI, TAKAYUKI ; KAWAUCHI, HIROSHI ; MUNEKATA, EISUKE</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c549t-ab0a5fba18d6c3cdeddecd70f3f8b27b8031c34043d3fcefe483244e6a3007623</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1980</creationdate><topic>Animals</topic><topic>Binding, Competitive</topic><topic>DCC-HONB method</topic><topic>Endorphins - chemical synthesis</topic><topic>Endorphins - pharmacology</topic><topic>In Vitro Techniques</topic><topic>Receptors, Opioid - drug effects</topic><topic>Salmon</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>FUJINO, MASAHIKO</creatorcontrib><creatorcontrib>KITADA, CHIEKO</creatorcontrib><creatorcontrib>WAKIMASU, MITSUHIRO</creatorcontrib><creatorcontrib>NISHIMURA, OSAMU</creatorcontrib><creatorcontrib>DOI, TAKAYUKI</creatorcontrib><creatorcontrib>KAWAUCHI, HIROSHI</creatorcontrib><creatorcontrib>MUNEKATA, EISUKE</creatorcontrib><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>Chemical & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>FUJINO, MASAHIKO</au><au>KITADA, CHIEKO</au><au>WAKIMASU, MITSUHIRO</au><au>NISHIMURA, OSAMU</au><au>DOI, TAKAYUKI</au><au>KAWAUCHI, HIROSHI</au><au>MUNEKATA, EISUKE</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Salmon Endorphin</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>1980-01-01</date><risdate>1980</risdate><volume>28</volume><issue>5</issue><spage>1655</spage><epage>1658</epage><pages>1655-1658</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><abstract>First synthesis of a nonacosapeptide corresponding to the entire amino acid sequence of salmon endorphin, Ac-Tyr-Gly-Gly-Phe-Met-Lys-Pro-Tyr-Thr-Lys-Gln-Ser-His-Lys-Pro-Leu-Ile-Thr-Leu-Leu-Lys-His-Ile-Thr-Leu-Lys-Asn-Glu-Gln-OH, and its des-acetyl derivative was described. Toward the synthesis of this hormone, five fragments, 1-7, 8-15, 16-18, 19-24 and 25-29, were prepared and the fragments were served as the building blocks for the final construction of the entire amino acid sequence of the hormone. The final deprotection of the fully protected peptide was achieved by treatment with trifluoroacetic acid and the purification of the synthetic peptides was effected by a column chromatography on CM-cellulose and then Sephadex LH-20. The synthetic acetylated nonacosapeptide was compared with purified natural salmon endorphin by means of chromatography, electrophoresis and also enzymatic digestion and found to be indistinguishable from natural isolated salmon endorphin. The opiate activity of the synthetic salmon endorphin and des-acetyl salmon endorphin was also described.</abstract><cop>Japan</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>6250730</pmid><doi>10.1248/cpb.28.1655</doi><tpages>4</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Chemical and Pharmaceutical Bulletin, 1980/05/25, Vol.28(5), pp.1655-1658 |
| issn | 0009-2363 1347-5223 |
| language | eng |
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| source | J-STAGE Free; MEDLINE; EZB-FREE-00999 freely available EZB journals; Free Full-Text Journals in Chemistry |
| subjects | Animals Binding, Competitive DCC-HONB method Endorphins - chemical synthesis Endorphins - pharmacology In Vitro Techniques Receptors, Opioid - drug effects Salmon |
| title | Synthesis of Salmon Endorphin |
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