Thermolysin-Catalyzed Synthesis of Peptide Amides
Enzymatic condensation by thermolysin between various amino acid amides and Naprotected or unprotected peptides was examined.As models, three protected tetrapeptide amides, Boc-Trp-Met-Asp-X, Boc-Ser-Glu-Ala-X and Boc-Ser-Lys-Ala-X, and two unprotected tetrapeptide amides, H-Trp-Met-Asp-X and H-Phe-...
Gespeichert in:
| Veröffentlicht in: | Chemical & pharmaceutical bulletin 1988/11/25, Vol.36(11), pp.4345-4354 |
|---|---|
| Hauptverfasser: | , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 4354 |
|---|---|
| container_issue | 11 |
| container_start_page | 4345 |
| container_title | Chemical & pharmaceutical bulletin |
| container_volume | 36 |
| creator | SAKINA, KIYOSHI KAWAZURA, KEIKO MORIHARA, KAZUYUKI YAJIMA, HARUAKI |
| description | Enzymatic condensation by thermolysin between various amino acid amides and Naprotected or unprotected peptides was examined.As models, three protected tetrapeptide amides, Boc-Trp-Met-Asp-X, Boc-Ser-Glu-Ala-X and Boc-Ser-Lys-Ala-X, and two unprotected tetrapeptide amides, H-Trp-Met-Asp-X and H-Phe-Met-Arg-X, were prepared [X=Phe-NH2, Leu-NH2, Phe-NHEt, Val-NH2, Ala-NH2, (p-fluoro) Phe-NH2], and the effects of various experimental conditions (pH, solvent and time) were examined.In addition, the C-terminal of oxidized insulin B-chain was elongated to an amide by addition of various amides mentioned above with the aid of thermolysin. |
| doi_str_mv | 10.1248/cpb.36.4345 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_78748920</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>3132530341</sourcerecordid><originalsourceid>FETCH-LOGICAL-c668t-6cd41ced2e2cd26391fd122aaa44efd6cee6d71646434ee9abe240f875cbbf1f3</originalsourceid><addsrcrecordid>eNqFkE1rGzEQhkVJSN00p54LhpReyroaSavVHoNpPsCQQJyz0Eqjes1-ONL64Pz6aPHiQi69jA7vw7yah5BvQBfAhPptd9WCy4XgIv9EZsBFkeWM8TMyo5SWGeOSfyZfYtxSynJa8AtywZmQlPIZgfUGQ9s3h1h32dIMpjm8oZs_H7phg7GO897Pn3A31A7nN22a8Ss596aJeDW9l-Tl9s96eZ-tHu8eljerzEqphkxaJ8CiY8isY5KX4B0wZowRAr2TFlG6AqSQ6d-IpamQCepVkduq8uD5Jfl53LsL_ese46DbOlpsGtNhv4-6UIVQJaP_BSEHKUuhEnj9Adz2-9ClIzQkHSBzgCJRv46UDX2MAb3ehbo14aCB6tG3Tr41l3r0nejv08591aI7sZPglP-YchOtaXwwna3jCZNKUQoiYbdHbBsH8xdPuQlDbRscK6HM1VgLMM2x_x-wMUFjx98BF-CfMg</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1460165117</pqid></control><display><type>article</type><title>Thermolysin-Catalyzed Synthesis of Peptide Amides</title><source>J-STAGE Free</source><source>MEDLINE</source><source>Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals</source><source>Free Full-Text Journals in Chemistry</source><creator>SAKINA, KIYOSHI ; KAWAZURA, KEIKO ; MORIHARA, KAZUYUKI ; YAJIMA, HARUAKI</creator><creatorcontrib>SAKINA, KIYOSHI ; KAWAZURA, KEIKO ; MORIHARA, KAZUYUKI ; YAJIMA, HARUAKI</creatorcontrib><description>Enzymatic condensation by thermolysin between various amino acid amides and Naprotected or unprotected peptides was examined.As models, three protected tetrapeptide amides, Boc-Trp-Met-Asp-X, Boc-Ser-Glu-Ala-X and Boc-Ser-Lys-Ala-X, and two unprotected tetrapeptide amides, H-Trp-Met-Asp-X and H-Phe-Met-Arg-X, were prepared [X=Phe-NH2, Leu-NH2, Phe-NHEt, Val-NH2, Ala-NH2, (p-fluoro) Phe-NH2], and the effects of various experimental conditions (pH, solvent and time) were examined.In addition, the C-terminal of oxidized insulin B-chain was elongated to an amide by addition of various amides mentioned above with the aid of thermolysin.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.36.4345</identifier><identifier>PMID: 3246003</identifier><identifier>CODEN: CPBTAL</identifier><language>eng</language><publisher>Tokyo: The Pharmaceutical Society of Japan</publisher><subject>Amides - chemical synthesis ; Catalysis ; Chemical Phenomena ; Chemistry ; enzymatic synthesis ; Exact sciences and technology ; FMRF-NH2 ; optimal pH conditions ; Organic chemistry ; oxidized insulin B-Phe31-NH2 ; peptide amide synthesis ; Peptides ; Peptides - chemical synthesis ; Preparations and properties ; tetragastrin ; Thermolysin ; thermolysin-catalyzed synthesis</subject><ispartof>Chemical and Pharmaceutical Bulletin, 1988/11/25, Vol.36(11), pp.4345-4354</ispartof><rights>The Pharmaceutical Society of Japan</rights><rights>1990 INIST-CNRS</rights><rights>Copyright Japan Science and Technology Agency 1988</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c668t-6cd41ced2e2cd26391fd122aaa44efd6cee6d71646434ee9abe240f875cbbf1f3</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,1877,4010,27900,27901,27902</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=6880014$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/3246003$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>SAKINA, KIYOSHI</creatorcontrib><creatorcontrib>KAWAZURA, KEIKO</creatorcontrib><creatorcontrib>MORIHARA, KAZUYUKI</creatorcontrib><creatorcontrib>YAJIMA, HARUAKI</creatorcontrib><title>Thermolysin-Catalyzed Synthesis of Peptide Amides</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>Enzymatic condensation by thermolysin between various amino acid amides and Naprotected or unprotected peptides was examined.As models, three protected tetrapeptide amides, Boc-Trp-Met-Asp-X, Boc-Ser-Glu-Ala-X and Boc-Ser-Lys-Ala-X, and two unprotected tetrapeptide amides, H-Trp-Met-Asp-X and H-Phe-Met-Arg-X, were prepared [X=Phe-NH2, Leu-NH2, Phe-NHEt, Val-NH2, Ala-NH2, (p-fluoro) Phe-NH2], and the effects of various experimental conditions (pH, solvent and time) were examined.In addition, the C-terminal of oxidized insulin B-chain was elongated to an amide by addition of various amides mentioned above with the aid of thermolysin.</description><subject>Amides - chemical synthesis</subject><subject>Catalysis</subject><subject>Chemical Phenomena</subject><subject>Chemistry</subject><subject>enzymatic synthesis</subject><subject>Exact sciences and technology</subject><subject>FMRF-NH2</subject><subject>optimal pH conditions</subject><subject>Organic chemistry</subject><subject>oxidized insulin B-Phe31-NH2</subject><subject>peptide amide synthesis</subject><subject>Peptides</subject><subject>Peptides - chemical synthesis</subject><subject>Preparations and properties</subject><subject>tetragastrin</subject><subject>Thermolysin</subject><subject>thermolysin-catalyzed synthesis</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1988</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkE1rGzEQhkVJSN00p54LhpReyroaSavVHoNpPsCQQJyz0Eqjes1-ONL64Pz6aPHiQi69jA7vw7yah5BvQBfAhPptd9WCy4XgIv9EZsBFkeWM8TMyo5SWGeOSfyZfYtxSynJa8AtywZmQlPIZgfUGQ9s3h1h32dIMpjm8oZs_H7phg7GO897Pn3A31A7nN22a8Ss596aJeDW9l-Tl9s96eZ-tHu8eljerzEqphkxaJ8CiY8isY5KX4B0wZowRAr2TFlG6AqSQ6d-IpamQCepVkduq8uD5Jfl53LsL_ese46DbOlpsGtNhv4-6UIVQJaP_BSEHKUuhEnj9Adz2-9ClIzQkHSBzgCJRv46UDX2MAb3ehbo14aCB6tG3Tr41l3r0nejv08591aI7sZPglP-YchOtaXwwna3jCZNKUQoiYbdHbBsH8xdPuQlDbRscK6HM1VgLMM2x_x-wMUFjx98BF-CfMg</recordid><startdate>1988</startdate><enddate>1988</enddate><creator>SAKINA, KIYOSHI</creator><creator>KAWAZURA, KEIKO</creator><creator>MORIHARA, KAZUYUKI</creator><creator>YAJIMA, HARUAKI</creator><general>The Pharmaceutical Society of Japan</general><general>Maruzen</general><general>Japan Science and Technology Agency</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>7TK</scope><scope>7TM</scope><scope>7U9</scope><scope>H94</scope><scope>7QL</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>M81</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>1988</creationdate><title>Thermolysin-Catalyzed Synthesis of Peptide Amides</title><author>SAKINA, KIYOSHI ; KAWAZURA, KEIKO ; MORIHARA, KAZUYUKI ; YAJIMA, HARUAKI</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c668t-6cd41ced2e2cd26391fd122aaa44efd6cee6d71646434ee9abe240f875cbbf1f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1988</creationdate><topic>Amides - chemical synthesis</topic><topic>Catalysis</topic><topic>Chemical Phenomena</topic><topic>Chemistry</topic><topic>enzymatic synthesis</topic><topic>Exact sciences and technology</topic><topic>FMRF-NH2</topic><topic>optimal pH conditions</topic><topic>Organic chemistry</topic><topic>oxidized insulin B-Phe31-NH2</topic><topic>peptide amide synthesis</topic><topic>Peptides</topic><topic>Peptides - chemical synthesis</topic><topic>Preparations and properties</topic><topic>tetragastrin</topic><topic>Thermolysin</topic><topic>thermolysin-catalyzed synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>SAKINA, KIYOSHI</creatorcontrib><creatorcontrib>KAWAZURA, KEIKO</creatorcontrib><creatorcontrib>MORIHARA, KAZUYUKI</creatorcontrib><creatorcontrib>YAJIMA, HARUAKI</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>Neurosciences Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>Bacteriology Abstracts (Microbiology B)</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biochemistry Abstracts 3</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>SAKINA, KIYOSHI</au><au>KAWAZURA, KEIKO</au><au>MORIHARA, KAZUYUKI</au><au>YAJIMA, HARUAKI</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Thermolysin-Catalyzed Synthesis of Peptide Amides</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>1988</date><risdate>1988</risdate><volume>36</volume><issue>11</issue><spage>4345</spage><epage>4354</epage><pages>4345-4354</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><coden>CPBTAL</coden><abstract>Enzymatic condensation by thermolysin between various amino acid amides and Naprotected or unprotected peptides was examined.As models, three protected tetrapeptide amides, Boc-Trp-Met-Asp-X, Boc-Ser-Glu-Ala-X and Boc-Ser-Lys-Ala-X, and two unprotected tetrapeptide amides, H-Trp-Met-Asp-X and H-Phe-Met-Arg-X, were prepared [X=Phe-NH2, Leu-NH2, Phe-NHEt, Val-NH2, Ala-NH2, (p-fluoro) Phe-NH2], and the effects of various experimental conditions (pH, solvent and time) were examined.In addition, the C-terminal of oxidized insulin B-chain was elongated to an amide by addition of various amides mentioned above with the aid of thermolysin.</abstract><cop>Tokyo</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>3246003</pmid><doi>10.1248/cpb.36.4345</doi><tpages>10</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0009-2363 |
| ispartof | Chemical and Pharmaceutical Bulletin, 1988/11/25, Vol.36(11), pp.4345-4354 |
| issn | 0009-2363 1347-5223 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_78748920 |
| source | J-STAGE Free; MEDLINE; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; Free Full-Text Journals in Chemistry |
| subjects | Amides - chemical synthesis Catalysis Chemical Phenomena Chemistry enzymatic synthesis Exact sciences and technology FMRF-NH2 optimal pH conditions Organic chemistry oxidized insulin B-Phe31-NH2 peptide amide synthesis Peptides Peptides - chemical synthesis Preparations and properties tetragastrin Thermolysin thermolysin-catalyzed synthesis |
| title | Thermolysin-Catalyzed Synthesis of Peptide Amides |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-02T19%3A31%3A47IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Thermolysin-Catalyzed%20Synthesis%20of%20Peptide%20Amides&rft.jtitle=Chemical%20&%20pharmaceutical%20bulletin&rft.au=SAKINA,%20KIYOSHI&rft.date=1988&rft.volume=36&rft.issue=11&rft.spage=4345&rft.epage=4354&rft.pages=4345-4354&rft.issn=0009-2363&rft.eissn=1347-5223&rft.coden=CPBTAL&rft_id=info:doi/10.1248/cpb.36.4345&rft_dat=%3Cproquest_cross%3E3132530341%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1460165117&rft_id=info:pmid/3246003&rfr_iscdi=true |