Studies on Peptides. CXXXIX. : Solution Synthesis of a 42-Residue Peptide Corresponding to the Entire Amino Acid Sequence of Human Glucose-Dependent Insulinotropic Polypeptide (GIP)
Eight peptide fragments were prepared by known amide-forming reactions as building blocks for the solution synthesis of the dotetracontapeptide corresponding to the entire amino acid sequence of human intestinal GIP (gastric inhibitory polypeptide or glucose-dependent insulinotropic polypeptide). Be...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 1986/06/25, Vol.34(6), pp.2397-2410 |
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| creator | FUJII, NOBUTAKA SAKURAI, MITSUYA AKAJI, KENICHI NOMIZU, MOTOYOSHI YAJIMA, HARUAKI MIZUTA, KAZUHIKO AONO, MITSURU MORIGA, MOTOYUKI INOUE, KAZUTOMO HOSOTANI, RYO TOBE, TAKAYOSHI |
| description | Eight peptide fragments were prepared by known amide-forming reactions as building blocks for the solution synthesis of the dotetracontapeptide corresponding to the entire amino acid sequence of human intestinal GIP (gastric inhibitory polypeptide or glucose-dependent insulinotropic polypeptide). Besides Lys(Z), Trp(Mts) and Gln-OBzl, two new amino acid derivatives, Asp(OChp) and Glu(OChp) [Mts=mesitylenesulfonyl, Chp=cycloheptyl], were employed to suppress various side reactions. These fragments were successively assembled by the azide procedure to minimize racemization and all protecting groups employed were removed from the protected GIP by using 1M trifluoromethanesulfonic acid-thioanisole in trifluoroacetic acid.Synthetic GIP exhibited a significant glucose-dependent insulinotropic activity in dogs, but failed to produce any notable anti-gastric activity in rats. |
| doi_str_mv | 10.1248/cpb.34.2397 |
| format | Article |
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CXXXIX. : Solution Synthesis of a 42-Residue Peptide Corresponding to the Entire Amino Acid Sequence of Human Glucose-Dependent Insulinotropic Polypeptide (GIP)</title><source>J-STAGE Free</source><source>MEDLINE</source><source>EZB-FREE-00999 freely available EZB journals</source><source>Free Full-Text Journals in Chemistry</source><creator>FUJII, NOBUTAKA ; SAKURAI, MITSUYA ; AKAJI, KENICHI ; NOMIZU, MOTOYOSHI ; YAJIMA, HARUAKI ; MIZUTA, KAZUHIKO ; AONO, MITSURU ; MORIGA, MOTOYUKI ; INOUE, KAZUTOMO ; HOSOTANI, RYO ; TOBE, TAKAYOSHI</creator><creatorcontrib>FUJII, NOBUTAKA ; SAKURAI, MITSUYA ; AKAJI, KENICHI ; NOMIZU, MOTOYOSHI ; YAJIMA, HARUAKI ; MIZUTA, KAZUHIKO ; AONO, MITSURU ; MORIGA, MOTOYUKI ; INOUE, KAZUTOMO ; HOSOTANI, RYO ; TOBE, TAKAYOSHI</creatorcontrib><description>Eight peptide fragments were prepared by known amide-forming reactions as building blocks for the solution synthesis of the dotetracontapeptide corresponding to the entire amino acid sequence of human intestinal GIP (gastric inhibitory polypeptide or glucose-dependent insulinotropic polypeptide). Besides Lys(Z), Trp(Mts) and Gln-OBzl, two new amino acid derivatives, Asp(OChp) and Glu(OChp) [Mts=mesitylenesulfonyl, Chp=cycloheptyl], were employed to suppress various side reactions. These fragments were successively assembled by the azide procedure to minimize racemization and all protecting groups employed were removed from the protected GIP by using 1M trifluoromethanesulfonic acid-thioanisole in trifluoroacetic acid.Synthetic GIP exhibited a significant glucose-dependent insulinotropic activity in dogs, but failed to produce any notable anti-gastric activity in rats.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.34.2397</identifier><identifier>PMID: 3769062</identifier><identifier>CODEN: CPBTAL</identifier><language>eng</language><publisher>Tokyo: The Pharmaceutical Society of Japan</publisher><subject>Amino Acid Sequence ; Chemistry ; Chromatography, High Pressure Liquid ; Exact sciences and technology ; gastric inhibition ; gastric inhibitory peptide ; Gastric Inhibitory Polypeptide - analysis ; Gastric Inhibitory Polypeptide - chemical synthesis ; Humans ; man ; Organic chemistry ; peptide synthesis ; Peptides ; Preparations and properties</subject><ispartof>Chemical and Pharmaceutical Bulletin, 1986/06/25, Vol.34(6), pp.2397-2410</ispartof><rights>The Pharmaceutical Society of Japan</rights><rights>1987 INIST-CNRS</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5537-be3bba017a1749f75b5c77b1eb664ddce2025968dabd3a890ff5ba924dde05cc3</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>315,781,785,1884,4025,27928,27929,27930</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=7947615$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/3769062$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>FUJII, NOBUTAKA</creatorcontrib><creatorcontrib>SAKURAI, MITSUYA</creatorcontrib><creatorcontrib>AKAJI, KENICHI</creatorcontrib><creatorcontrib>NOMIZU, MOTOYOSHI</creatorcontrib><creatorcontrib>YAJIMA, HARUAKI</creatorcontrib><creatorcontrib>MIZUTA, KAZUHIKO</creatorcontrib><creatorcontrib>AONO, MITSURU</creatorcontrib><creatorcontrib>MORIGA, MOTOYUKI</creatorcontrib><creatorcontrib>INOUE, KAZUTOMO</creatorcontrib><creatorcontrib>HOSOTANI, RYO</creatorcontrib><creatorcontrib>TOBE, TAKAYOSHI</creatorcontrib><title>Studies on Peptides. CXXXIX. : Solution Synthesis of a 42-Residue Peptide Corresponding to the Entire Amino Acid Sequence of Human Glucose-Dependent Insulinotropic Polypeptide (GIP)</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>Eight peptide fragments were prepared by known amide-forming reactions as building blocks for the solution synthesis of the dotetracontapeptide corresponding to the entire amino acid sequence of human intestinal GIP (gastric inhibitory polypeptide or glucose-dependent insulinotropic polypeptide). Besides Lys(Z), Trp(Mts) and Gln-OBzl, two new amino acid derivatives, Asp(OChp) and Glu(OChp) [Mts=mesitylenesulfonyl, Chp=cycloheptyl], were employed to suppress various side reactions. These fragments were successively assembled by the azide procedure to minimize racemization and all protecting groups employed were removed from the protected GIP by using 1M trifluoromethanesulfonic acid-thioanisole in trifluoroacetic acid.Synthetic GIP exhibited a significant glucose-dependent insulinotropic activity in dogs, but failed to produce any notable anti-gastric activity in rats.</description><subject>Amino Acid Sequence</subject><subject>Chemistry</subject><subject>Chromatography, High Pressure Liquid</subject><subject>Exact sciences and technology</subject><subject>gastric inhibition</subject><subject>gastric inhibitory peptide</subject><subject>Gastric Inhibitory Polypeptide - analysis</subject><subject>Gastric Inhibitory Polypeptide - chemical synthesis</subject><subject>Humans</subject><subject>man</subject><subject>Organic chemistry</subject><subject>peptide synthesis</subject><subject>Peptides</subject><subject>Preparations and properties</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1986</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkU-LEzEYxgdR1nX15FnIQUSRqZn8mTTeSnftFhYsVqG3IZO8s5tlmswmmUM_mN_PDK316CUhPL_3ecL7FMXbCs8qwuZf9NDOKJsRKsWz4rKiTJScEPq8uMQYy5LQmr4sXsX4iDHhWNCL4oKKWuKaXBa_t2k0FiLyDm1gSNZAnKHlbrdb72boK9r6fkw2i9uDSw8QbSY7pBAj5Y_8MiP8HUNLHwLEwTtj3T1KHmUe3bhkA6DF3jqPFtoatIWnEZyGyed23CuHVv2ofYTyGgZwBlxCaxfHPk-k4Aer0cb3h-GU8nG13nx6XbzoVB_hzem-Kn59u_m5vC3vvq_Wy8VdqTmnomyBtq3ClVCVYLITvOVaiLaCtq6ZMRpIXois50a1hqq5xF3HWyVJ1gBzrelV8eHoOwSffx1Ts7dRQ98rB36MjRBY5k3O_wtWjNeSMZLBz0dQBx9jgK4Zgt2rcGgq3ExtNrnNhrJmajPT7062Y7sHc2ZP9WX9_UlXUau-C8ppG8-YkEzUFc_Y9RF7jEndw1lXIVndwxRZST6fYuvjMaX_kx9UaMDRP3XcwUM</recordid><startdate>1986</startdate><enddate>1986</enddate><creator>FUJII, NOBUTAKA</creator><creator>SAKURAI, MITSUYA</creator><creator>AKAJI, KENICHI</creator><creator>NOMIZU, MOTOYOSHI</creator><creator>YAJIMA, HARUAKI</creator><creator>MIZUTA, KAZUHIKO</creator><creator>AONO, MITSURU</creator><creator>MORIGA, MOTOYUKI</creator><creator>INOUE, KAZUTOMO</creator><creator>HOSOTANI, RYO</creator><creator>TOBE, TAKAYOSHI</creator><general>The Pharmaceutical Society of Japan</general><general>Maruzen</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>1986</creationdate><title>Studies on Peptides. CXXXIX. : Solution Synthesis of a 42-Residue Peptide Corresponding to the Entire Amino Acid Sequence of Human Glucose-Dependent Insulinotropic Polypeptide (GIP)</title><author>FUJII, NOBUTAKA ; SAKURAI, MITSUYA ; AKAJI, KENICHI ; NOMIZU, MOTOYOSHI ; YAJIMA, HARUAKI ; MIZUTA, KAZUHIKO ; AONO, MITSURU ; MORIGA, MOTOYUKI ; INOUE, KAZUTOMO ; HOSOTANI, RYO ; TOBE, TAKAYOSHI</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5537-be3bba017a1749f75b5c77b1eb664ddce2025968dabd3a890ff5ba924dde05cc3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1986</creationdate><topic>Amino Acid Sequence</topic><topic>Chemistry</topic><topic>Chromatography, High Pressure Liquid</topic><topic>Exact sciences and technology</topic><topic>gastric inhibition</topic><topic>gastric inhibitory peptide</topic><topic>Gastric Inhibitory Polypeptide - analysis</topic><topic>Gastric Inhibitory Polypeptide - chemical synthesis</topic><topic>Humans</topic><topic>man</topic><topic>Organic chemistry</topic><topic>peptide synthesis</topic><topic>Peptides</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>FUJII, NOBUTAKA</creatorcontrib><creatorcontrib>SAKURAI, MITSUYA</creatorcontrib><creatorcontrib>AKAJI, KENICHI</creatorcontrib><creatorcontrib>NOMIZU, MOTOYOSHI</creatorcontrib><creatorcontrib>YAJIMA, HARUAKI</creatorcontrib><creatorcontrib>MIZUTA, KAZUHIKO</creatorcontrib><creatorcontrib>AONO, MITSURU</creatorcontrib><creatorcontrib>MORIGA, MOTOYUKI</creatorcontrib><creatorcontrib>INOUE, KAZUTOMO</creatorcontrib><creatorcontrib>HOSOTANI, RYO</creatorcontrib><creatorcontrib>TOBE, TAKAYOSHI</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>Chemical & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>FUJII, NOBUTAKA</au><au>SAKURAI, MITSUYA</au><au>AKAJI, KENICHI</au><au>NOMIZU, MOTOYOSHI</au><au>YAJIMA, HARUAKI</au><au>MIZUTA, KAZUHIKO</au><au>AONO, MITSURU</au><au>MORIGA, MOTOYUKI</au><au>INOUE, KAZUTOMO</au><au>HOSOTANI, RYO</au><au>TOBE, TAKAYOSHI</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Studies on Peptides. CXXXIX. : Solution Synthesis of a 42-Residue Peptide Corresponding to the Entire Amino Acid Sequence of Human Glucose-Dependent Insulinotropic Polypeptide (GIP)</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>1986</date><risdate>1986</risdate><volume>34</volume><issue>6</issue><spage>2397</spage><epage>2410</epage><pages>2397-2410</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><coden>CPBTAL</coden><abstract>Eight peptide fragments were prepared by known amide-forming reactions as building blocks for the solution synthesis of the dotetracontapeptide corresponding to the entire amino acid sequence of human intestinal GIP (gastric inhibitory polypeptide or glucose-dependent insulinotropic polypeptide). Besides Lys(Z), Trp(Mts) and Gln-OBzl, two new amino acid derivatives, Asp(OChp) and Glu(OChp) [Mts=mesitylenesulfonyl, Chp=cycloheptyl], were employed to suppress various side reactions. 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| ispartof | Chemical and Pharmaceutical Bulletin, 1986/06/25, Vol.34(6), pp.2397-2410 |
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| 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 | Amino Acid Sequence Chemistry Chromatography, High Pressure Liquid Exact sciences and technology gastric inhibition gastric inhibitory peptide Gastric Inhibitory Polypeptide - analysis Gastric Inhibitory Polypeptide - chemical synthesis Humans man Organic chemistry peptide synthesis Peptides Preparations and properties |
| title | Studies on Peptides. CXXXIX. : Solution Synthesis of a 42-Residue Peptide Corresponding to the Entire Amino Acid Sequence of Human Glucose-Dependent Insulinotropic Polypeptide (GIP) |
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