Synthesis and Absolute Configuration of Wybutine, the Fluorescent Minor Base from Phenylalanine Transfer Ribonucleic Acids
The phosphonium chloride 6 having an optically active amino acid moiety was synthesized from (S)-serine benzylester tosylate (2b) through a six-step route. The utility of 6 as a reagent for the Witting reaction was exemplified in the olefination with benzaldehyde, affording the (E)-β, γ-unsaturated...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 1991/06/25, Vol.39(6), pp.1407-1414 |
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| container_issue | 6 |
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| container_title | Chemical & pharmaceutical bulletin |
| container_volume | 39 |
| creator | ITAYA, Taisuke MIZUTANI, Akemi IIDA, Takehiko |
| description | The phosphonium chloride 6 having an optically active amino acid moiety was synthesized from (S)-serine benzylester tosylate (2b) through a six-step route. The utility of 6 as a reagent for the Witting reaction was exemplified in the olefination with benzaldehyde, affording the (E)-β, γ-unsaturated amino acid derivative 11 as a sole geometrical ispmer. This new method of amino acid homologation was successuflly employed for the first chiral synthesis of wybutine (1c), the minor base isolated from yeast phenylalanine transfer ribonucleic acids : the Wittig reaction between 6 and the tricyclic aldehyde 16 followed successively by methylation and catalytic reduction afforded 1c. Comparison of wybutine with synthetic 1c has unequivocally established that wybutine has an S configuration. |
| doi_str_mv | 10.1248/cpb.39.1407 |
| format | Article |
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The utility of 6 as a reagent for the Witting reaction was exemplified in the olefination with benzaldehyde, affording the (E)-β, γ-unsaturated amino acid derivative 11 as a sole geometrical ispmer. This new method of amino acid homologation was successuflly employed for the first chiral synthesis of wybutine (1c), the minor base isolated from yeast phenylalanine transfer ribonucleic acids : the Wittig reaction between 6 and the tricyclic aldehyde 16 followed successively by methylation and catalytic reduction afforded 1c. Comparison of wybutine with synthetic 1c has unequivocally established that wybutine has an S configuration.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.39.1407</identifier><identifier>CODEN: CPBTAL</identifier><language>eng</language><publisher>Tokyo: The Pharmaceutical Society of Japan</publisher><subject>absolute configuration ; alanine synthon ; amino acid homologation ; Chemistry ; chiral synthesis ; Exact sciences and technology ; Heterocyclic compounds ; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings ; hypermodified base ; Organic chemistry ; phenylalanine transfer ribonucleic acid ; Preparations and properties ; stereoselective olefination ; Wittig reaction ; wybutine ; β, γ-unsaturated amino acid</subject><ispartof>Chemical and Pharmaceutical Bulletin, 1991/06/25, Vol.39(6), pp.1407-1414</ispartof><rights>The Pharmaceutical Society of Japan</rights><rights>1992 INIST-CNRS</rights><rights>Copyright Japan Science and Technology Agency 1991</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c613t-5d4d492b1f9f66bba27961a9208fd97034e2a94748c881539edecdd7703bc68e3</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=4963376$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>ITAYA, Taisuke</creatorcontrib><creatorcontrib>MIZUTANI, Akemi</creatorcontrib><creatorcontrib>IIDA, Takehiko</creatorcontrib><title>Synthesis and Absolute Configuration of Wybutine, the Fluorescent Minor Base from Phenylalanine Transfer Ribonucleic Acids</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>The phosphonium chloride 6 having an optically active amino acid moiety was synthesized from (S)-serine benzylester tosylate (2b) through a six-step route. The utility of 6 as a reagent for the Witting reaction was exemplified in the olefination with benzaldehyde, affording the (E)-β, γ-unsaturated amino acid derivative 11 as a sole geometrical ispmer. This new method of amino acid homologation was successuflly employed for the first chiral synthesis of wybutine (1c), the minor base isolated from yeast phenylalanine transfer ribonucleic acids : the Wittig reaction between 6 and the tricyclic aldehyde 16 followed successively by methylation and catalytic reduction afforded 1c. Comparison of wybutine with synthetic 1c has unequivocally established that wybutine has an S configuration.</description><subject>absolute configuration</subject><subject>alanine synthon</subject><subject>amino acid homologation</subject><subject>Chemistry</subject><subject>chiral synthesis</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings</subject><subject>hypermodified base</subject><subject>Organic chemistry</subject><subject>phenylalanine transfer ribonucleic acid</subject><subject>Preparations and properties</subject><subject>stereoselective olefination</subject><subject>Wittig reaction</subject><subject>wybutine</subject><subject>β, γ-unsaturated amino acid</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1991</creationdate><recordtype>article</recordtype><recordid>eNpdkU2LFDEYhIMoOK6e_AMBxYvbY7463TmOo6vCiqIrHkM6_WYnQ08yJunD-Os3zSwreEkO9bxFUYXQS0rWlIn-nT0Oa67WVJDuEVpRLrqmZYw_RitCiGoYl_wpepbznhDWko6v0N-fp1B2kH3GJox4M-Q4zQXwNgbnb-dkio8BR4d_n4a5-ACXuOL4appjgmwhFPzVh5jwe5MBuxQP-PsOwmkykwkVxzfJhOwg4R9-iGG2E3iLN9aP-Tl64syU4cX9f4F-XX282X5urr99-rLdXDdWUl6adhSjUGygTjkph8GwTklqFCO9G1VHuABmlOhEb_uetlzBCHYcu6oMVvbAL9Cbs-8xxT8z5KIPviafakCIc9ZUEkoZVxV89R-4j3MKNZumQhJW62x5pd6eKZtizgmcPiZ_MOmkKdHLCrquoLnSywqVfn3vabI1k6ttWJ8fToSSnHeyYh_O2D4XcwsPuknF18oWS6rafrGV52dx_yfvTNIQ-B1QtKBB</recordid><startdate>1991</startdate><enddate>1991</enddate><creator>ITAYA, Taisuke</creator><creator>MIZUTANI, Akemi</creator><creator>IIDA, Takehiko</creator><general>The Pharmaceutical Society of Japan</general><general>Maruzen</general><general>Japan Science and Technology Agency</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TK</scope><scope>7TM</scope><scope>7U9</scope><scope>H94</scope></search><sort><creationdate>1991</creationdate><title>Synthesis and Absolute Configuration of Wybutine, the Fluorescent Minor Base from Phenylalanine Transfer Ribonucleic Acids</title><author>ITAYA, Taisuke ; MIZUTANI, Akemi ; IIDA, Takehiko</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c613t-5d4d492b1f9f66bba27961a9208fd97034e2a94748c881539edecdd7703bc68e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1991</creationdate><topic>absolute configuration</topic><topic>alanine synthon</topic><topic>amino acid homologation</topic><topic>Chemistry</topic><topic>chiral synthesis</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings</topic><topic>hypermodified base</topic><topic>Organic chemistry</topic><topic>phenylalanine transfer ribonucleic acid</topic><topic>Preparations and properties</topic><topic>stereoselective olefination</topic><topic>Wittig reaction</topic><topic>wybutine</topic><topic>β, γ-unsaturated amino acid</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>ITAYA, Taisuke</creatorcontrib><creatorcontrib>MIZUTANI, Akemi</creatorcontrib><creatorcontrib>IIDA, Takehiko</creatorcontrib><collection>Pascal-Francis</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><jtitle>Chemical & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>ITAYA, Taisuke</au><au>MIZUTANI, Akemi</au><au>IIDA, Takehiko</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and Absolute Configuration of Wybutine, the Fluorescent Minor Base from Phenylalanine Transfer Ribonucleic Acids</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>1991</date><risdate>1991</risdate><volume>39</volume><issue>6</issue><spage>1407</spage><epage>1414</epage><pages>1407-1414</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><coden>CPBTAL</coden><abstract>The phosphonium chloride 6 having an optically active amino acid moiety was synthesized from (S)-serine benzylester tosylate (2b) through a six-step route. The utility of 6 as a reagent for the Witting reaction was exemplified in the olefination with benzaldehyde, affording the (E)-β, γ-unsaturated amino acid derivative 11 as a sole geometrical ispmer. This new method of amino acid homologation was successuflly employed for the first chiral synthesis of wybutine (1c), the minor base isolated from yeast phenylalanine transfer ribonucleic acids : the Wittig reaction between 6 and the tricyclic aldehyde 16 followed successively by methylation and catalytic reduction afforded 1c. Comparison of wybutine with synthetic 1c has unequivocally established that wybutine has an S configuration.</abstract><cop>Tokyo</cop><pub>The Pharmaceutical Society of Japan</pub><doi>10.1248/cpb.39.1407</doi><tpages>8</tpages><oa>free_for_read</oa></addata></record> |
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| identifier | ISSN: 0009-2363 |
| ispartof | Chemical and Pharmaceutical Bulletin, 1991/06/25, Vol.39(6), pp.1407-1414 |
| issn | 0009-2363 1347-5223 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_16011239 |
| source | J-STAGE Free; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; Free Full-Text Journals in Chemistry |
| subjects | absolute configuration alanine synthon amino acid homologation Chemistry chiral synthesis Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings hypermodified base Organic chemistry phenylalanine transfer ribonucleic acid Preparations and properties stereoselective olefination Wittig reaction wybutine β, γ-unsaturated amino acid |
| title | Synthesis and Absolute Configuration of Wybutine, the Fluorescent Minor Base from Phenylalanine Transfer Ribonucleic Acids |
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