Total Synthesis of WS9326A, a Potent Tachykinin Antagonist from Streptomyces violaceoniger
Total synthesis of the cyclic peptide lactone WS9326A, a potent tachykinin antagonist isolated from Streptomyces violaceoniger strain 9326, has been achieved via Cbz-Thr(Boc-allo-Thr-Asn-Ser(Bzl))-(E)ΔMeTyr-Leu-D-Phe-OTce, which was cyclized (Phe and allo-Thr) using an active ester method with N-hyd...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 1997/02/15, Vol.45(2), pp.236-242 |
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| container_title | Chemical & pharmaceutical bulletin |
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| creator | SHIGEMATSU, Nobuharu KAYAKIRI, Natsuko OKADA, Satoshi TANAKA, Hirokazu |
| description | Total synthesis of the cyclic peptide lactone WS9326A, a potent tachykinin antagonist isolated from Streptomyces violaceoniger strain 9326, has been achieved via Cbz-Thr(Boc-allo-Thr-Asn-Ser(Bzl))-(E)ΔMeTyr-Leu-D-Phe-OTce, which was cyclized (Phe and allo-Thr) using an active ester method with N-hydroxysuccinimide. Finally the unique N-acyl group, the 2-(1(Z)-pentenyl)cinnamoyl moiety, was introduced onto the amino group in the Thr unit. The key step of the synthesis involves the preparation of the E-isomer of the dehydro-N-mehyltyrosine (ΔMeTyr) unit. The debenzoxylation reaction of the threo- and erythro-isomers of β-benzoxy-N-methyltyrosine drivatives gave exclusively the Z-isomer of Cbz-Thr-ΔMeTyr(MOM)-OMe, which was then converted to the desired E-isomer by photochemical isomerization of Cbz-Thr(TBDMS)-(Z)ΔMeTyr(MOM)-Leu-D-Phe-OTce at a later step. |
| doi_str_mv | 10.1248/cpb.45.236 |
| format | Article |
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Finally the unique N-acyl group, the 2-(1(Z)-pentenyl)cinnamoyl moiety, was introduced onto the amino group in the Thr unit. The key step of the synthesis involves the preparation of the E-isomer of the dehydro-N-mehyltyrosine (ΔMeTyr) unit. The debenzoxylation reaction of the threo- and erythro-isomers of β-benzoxy-N-methyltyrosine drivatives gave exclusively the Z-isomer of Cbz-Thr-ΔMeTyr(MOM)-OMe, which was then converted to the desired E-isomer by photochemical isomerization of Cbz-Thr(TBDMS)-(Z)ΔMeTyr(MOM)-Leu-D-Phe-OTce at a later step.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.45.236</identifier><identifier>PMID: 9118439</identifier><identifier>CODEN: CPBTAL</identifier><language>eng</language><publisher>Tokyo: The Pharmaceutical Society of Japan</publisher><subject>Chemistry ; Chromatography, High Pressure Liquid ; cyclic peptide lactone ; Exact sciences and technology ; Isomerism ; Lactones - metabolism ; Organic chemistry ; Peptides ; Peptides, Cyclic - biosynthesis ; Peptides, Cyclic - metabolism ; photochemical isomerization ; Preparations and properties ; Streptomyces - metabolism ; Tachykinins - antagonists & inhibitors ; techykinin antagonist</subject><ispartof>Chemical and Pharmaceutical Bulletin, 1997/02/15, Vol.45(2), pp.236-242</ispartof><rights>The Pharmaceutical Society of Japan</rights><rights>1997 INIST-CNRS</rights><rights>Copyright Japan Science and Technology Agency 1997</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c658t-e1b85e1e7b2c5a9a2079d2d5eeb53ad62538456c1c28e60d1b48c36c1953638b3</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,1877,27901,27902</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=2612392$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/9118439$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>SHIGEMATSU, Nobuharu</creatorcontrib><creatorcontrib>KAYAKIRI, Natsuko</creatorcontrib><creatorcontrib>OKADA, Satoshi</creatorcontrib><creatorcontrib>TANAKA, Hirokazu</creatorcontrib><title>Total Synthesis of WS9326A, a Potent Tachykinin Antagonist from Streptomyces violaceoniger</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>Total synthesis of the cyclic peptide lactone WS9326A, a potent tachykinin antagonist isolated from Streptomyces violaceoniger strain 9326, has been achieved via Cbz-Thr(Boc-allo-Thr-Asn-Ser(Bzl))-(E)ΔMeTyr-Leu-D-Phe-OTce, which was cyclized (Phe and allo-Thr) using an active ester method with N-hydroxysuccinimide. Finally the unique N-acyl group, the 2-(1(Z)-pentenyl)cinnamoyl moiety, was introduced onto the amino group in the Thr unit. The key step of the synthesis involves the preparation of the E-isomer of the dehydro-N-mehyltyrosine (ΔMeTyr) unit. The debenzoxylation reaction of the threo- and erythro-isomers of β-benzoxy-N-methyltyrosine drivatives gave exclusively the Z-isomer of Cbz-Thr-ΔMeTyr(MOM)-OMe, which was then converted to the desired E-isomer by photochemical isomerization of Cbz-Thr(TBDMS)-(Z)ΔMeTyr(MOM)-Leu-D-Phe-OTce at a later step.</description><subject>Chemistry</subject><subject>Chromatography, High Pressure Liquid</subject><subject>cyclic peptide lactone</subject><subject>Exact sciences and technology</subject><subject>Isomerism</subject><subject>Lactones - metabolism</subject><subject>Organic chemistry</subject><subject>Peptides</subject><subject>Peptides, Cyclic - biosynthesis</subject><subject>Peptides, Cyclic - metabolism</subject><subject>photochemical isomerization</subject><subject>Preparations and properties</subject><subject>Streptomyces - metabolism</subject><subject>Tachykinins - antagonists & inhibitors</subject><subject>techykinin antagonist</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1997</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkc2rEzEUxYMoz1rduBcCigtxar4nsyzFL3ig0IrgJmQyd16nziR9SSr0vze1pYIbN7nknh_3cO9B6DklC8qEfuf27ULIBePqAZpRLupKMsYfohkhpKlKmz9GT1LaEcIkqfkNumko1YI3M_RjE7Id8fro8xbSkHDo8fd1w5lavsUWfw0ZfMYb67bHn4MfPF76bO-CH1LGfQwTXucI-xymo4OEfw1htA6KfAfxKXrU2zHBs0udo28f3m9Wn6rbLx8_r5a3lVNS5wpoqyVQqFvmpG0sI3XTsU4CtJLbTjHJtZDKUcc0KNLRVmjHy7-RZTHd8jl6fZ67j-H-ACmbaUgOxtF6CIdkaq2Vbmr6X5AqxgXjsoAv_wF34RB9WcJQoQinhAteqDdnysWQUoTe7OMw2Xg0lJhTLqbkYoQ0pwDm6MVl5KGdoLuilyCK_uqi2-Ts2Efr3ZCuGFOU8YYVbHXGdqnEAFfdxjy4EU6O5S76j-v5KeZ_1a2NBjz_DYyiq0g</recordid><startdate>19970201</startdate><enddate>19970201</enddate><creator>SHIGEMATSU, Nobuharu</creator><creator>KAYAKIRI, Natsuko</creator><creator>OKADA, Satoshi</creator><creator>TANAKA, Hirokazu</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>C1K</scope><scope>7X8</scope></search><sort><creationdate>19970201</creationdate><title>Total Synthesis of WS9326A, a Potent Tachykinin Antagonist from Streptomyces violaceoniger</title><author>SHIGEMATSU, Nobuharu ; KAYAKIRI, Natsuko ; OKADA, Satoshi ; TANAKA, Hirokazu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c658t-e1b85e1e7b2c5a9a2079d2d5eeb53ad62538456c1c28e60d1b48c36c1953638b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1997</creationdate><topic>Chemistry</topic><topic>Chromatography, High Pressure Liquid</topic><topic>cyclic peptide lactone</topic><topic>Exact sciences and technology</topic><topic>Isomerism</topic><topic>Lactones - metabolism</topic><topic>Organic chemistry</topic><topic>Peptides</topic><topic>Peptides, Cyclic - biosynthesis</topic><topic>Peptides, Cyclic - metabolism</topic><topic>photochemical isomerization</topic><topic>Preparations and properties</topic><topic>Streptomyces - metabolism</topic><topic>Tachykinins - antagonists & inhibitors</topic><topic>techykinin antagonist</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>SHIGEMATSU, Nobuharu</creatorcontrib><creatorcontrib>KAYAKIRI, Natsuko</creatorcontrib><creatorcontrib>OKADA, Satoshi</creatorcontrib><creatorcontrib>TANAKA, Hirokazu</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>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>SHIGEMATSU, Nobuharu</au><au>KAYAKIRI, Natsuko</au><au>OKADA, Satoshi</au><au>TANAKA, Hirokazu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Total Synthesis of WS9326A, a Potent Tachykinin Antagonist from Streptomyces violaceoniger</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>1997-02-01</date><risdate>1997</risdate><volume>45</volume><issue>2</issue><spage>236</spage><epage>242</epage><pages>236-242</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><coden>CPBTAL</coden><abstract>Total synthesis of the cyclic peptide lactone WS9326A, a potent tachykinin antagonist isolated from Streptomyces violaceoniger strain 9326, has been achieved via Cbz-Thr(Boc-allo-Thr-Asn-Ser(Bzl))-(E)ΔMeTyr-Leu-D-Phe-OTce, which was cyclized (Phe and allo-Thr) using an active ester method with N-hydroxysuccinimide. Finally the unique N-acyl group, the 2-(1(Z)-pentenyl)cinnamoyl moiety, was introduced onto the amino group in the Thr unit. The key step of the synthesis involves the preparation of the E-isomer of the dehydro-N-mehyltyrosine (ΔMeTyr) unit. The debenzoxylation reaction of the threo- and erythro-isomers of β-benzoxy-N-methyltyrosine drivatives gave exclusively the Z-isomer of Cbz-Thr-ΔMeTyr(MOM)-OMe, which was then converted to the desired E-isomer by photochemical isomerization of Cbz-Thr(TBDMS)-(Z)ΔMeTyr(MOM)-Leu-D-Phe-OTce at a later step.</abstract><cop>Tokyo</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>9118439</pmid><doi>10.1248/cpb.45.236</doi><tpages>7</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | Chemistry Chromatography, High Pressure Liquid cyclic peptide lactone Exact sciences and technology Isomerism Lactones - metabolism Organic chemistry Peptides Peptides, Cyclic - biosynthesis Peptides, Cyclic - metabolism photochemical isomerization Preparations and properties Streptomyces - metabolism Tachykinins - antagonists & inhibitors techykinin antagonist |
| title | Total Synthesis of WS9326A, a Potent Tachykinin Antagonist from Streptomyces violaceoniger |
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