The Reaction of S-Aminomethylthiamine with Acid Anhydride : The Synthesis of O, S-Bis (α-aminoacyl) thiamine
It was found that the reaction of S-aminomethylthiamine (II) with acid anhydride afforded the corresponding S-acylthiamine (III) or, O, S-diacylthiamine (IV). Furthermore the reaction of II with anhydrides (VII, IX, XII) of N-benzyloxycarbonyl-or N-t-butyloxycarbonyl-L-amino acid in tetrahydrofuran...
Gespeichert in:
| Veröffentlicht in: | Chemical & pharmaceutical bulletin 1976/05/25, Vol.24(5), pp.852-858 |
|---|---|
| Hauptverfasser: | , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 858 |
|---|---|
| container_issue | 5 |
| container_start_page | 852 |
| container_title | Chemical & pharmaceutical bulletin |
| container_volume | 24 |
| creator | YASUO, HARUNORI YONEDA, NAOTO MATSUOKA, YUZO |
| description | It was found that the reaction of S-aminomethylthiamine (II) with acid anhydride afforded the corresponding S-acylthiamine (III) or, O, S-diacylthiamine (IV). Furthermore the reaction of II with anhydrides (VII, IX, XII) of N-benzyloxycarbonyl-or N-t-butyloxycarbonyl-L-amino acid in tetrahydrofuran at -5-5° gave successfully the novel thiamine compounds with amino acid residues : O, S-bis (α-N-benzyloxycarbonyl-aminoacyl) thiamine (VIII) or O, S-bis (α-N-t-butyloxycarbonylaminoacyl) thiamine (X). O, S-Bis (α-aminoacyl) thiamine trihydrochloride (XI·3HCl) was obtained in good yield by the treatment of X with hydrogen chloride in ethyl acetate at -10°. Thiamine activities of VIII·HCl and XI·3HCl in thiamine deficient rats were similar to those of equimolar thiamine chloride hydrochloride (I-Cl·HCl). |
| doi_str_mv | 10.1248/cpb.24.852 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_83726203</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>83726203</sourcerecordid><originalsourceid>FETCH-LOGICAL-c444t-b0fcf837e85e0c5af390d5970994792bebff2c5f4b3fa85379b9d6ba139662883</originalsourceid><addsrcrecordid>eNpNkMtO3DAYhS1URIfLhn0lrypAZOr4ksTspqNykZCQynRtOc5vYpTLEHtU5bF4EZ6pTmdo2fwXnXO-xUHoNCXzlPLim1mXc8rnhaB7aJYynieCUvYJzQghMqEsY5_RoffPhFBBcnaADlJCU5rJGWpXNeCfoE1wfYd7ix-TReu6voVQj02onY4f4N8u1HhhXIUXXT1Wg6sAX-Ep-zh2oQbv_BR-uIz57_E-e3tNpmSvzdic43fOMdq3uvFwsttH6Nf1j9XyNrl_uLlbLu4TwzkPSUmssQXLoRBAjNCWSVIJmRMpeS5pCaW11AjLS2Z1IVguS1llpU6ZzDJaFOwIfd1y10P_sgEfVOu8gabRHfQbryKbZpSwaLzYGs3Qez-AVevBtXoYVUrU1K2K3SrKVew2mr_sqJuyheqD9W-ZUV9u9Wcf9BP80_UQnGlgQqVSFBNObEek_ldrPSjo2B-VHIw9</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>83726203</pqid></control><display><type>article</type><title>The Reaction of S-Aminomethylthiamine with Acid Anhydride : The Synthesis of O, S-Bis (α-aminoacyl) thiamine</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>YASUO, HARUNORI ; YONEDA, NAOTO ; MATSUOKA, YUZO</creator><creatorcontrib>YASUO, HARUNORI ; YONEDA, NAOTO ; MATSUOKA, YUZO</creatorcontrib><description>It was found that the reaction of S-aminomethylthiamine (II) with acid anhydride afforded the corresponding S-acylthiamine (III) or, O, S-diacylthiamine (IV). Furthermore the reaction of II with anhydrides (VII, IX, XII) of N-benzyloxycarbonyl-or N-t-butyloxycarbonyl-L-amino acid in tetrahydrofuran at -5-5° gave successfully the novel thiamine compounds with amino acid residues : O, S-bis (α-N-benzyloxycarbonyl-aminoacyl) thiamine (VIII) or O, S-bis (α-N-t-butyloxycarbonylaminoacyl) thiamine (X). O, S-Bis (α-aminoacyl) thiamine trihydrochloride (XI·3HCl) was obtained in good yield by the treatment of X with hydrogen chloride in ethyl acetate at -10°. Thiamine activities of VIII·HCl and XI·3HCl in thiamine deficient rats were similar to those of equimolar thiamine chloride hydrochloride (I-Cl·HCl).</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.24.852</identifier><identifier>PMID: 1021269</identifier><language>eng</language><publisher>Japan: The Pharmaceutical Society of Japan</publisher><subject>Animals ; Male ; Methods ; Rats ; Thiamine - analogs & derivatives ; Thiamine - chemical synthesis ; Thiamine - therapeutic use ; Thiamine Deficiency - drug therapy</subject><ispartof>Chemical and Pharmaceutical Bulletin, 1976/05/25, Vol.24(5), pp.852-858</ispartof><rights>The Pharmaceutical Society of Japan</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c444t-b0fcf837e85e0c5af390d5970994792bebff2c5f4b3fa85379b9d6ba139662883</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,1883,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/1021269$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>YASUO, HARUNORI</creatorcontrib><creatorcontrib>YONEDA, NAOTO</creatorcontrib><creatorcontrib>MATSUOKA, YUZO</creatorcontrib><title>The Reaction of S-Aminomethylthiamine with Acid Anhydride : The Synthesis of O, S-Bis (α-aminoacyl) thiamine</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>It was found that the reaction of S-aminomethylthiamine (II) with acid anhydride afforded the corresponding S-acylthiamine (III) or, O, S-diacylthiamine (IV). Furthermore the reaction of II with anhydrides (VII, IX, XII) of N-benzyloxycarbonyl-or N-t-butyloxycarbonyl-L-amino acid in tetrahydrofuran at -5-5° gave successfully the novel thiamine compounds with amino acid residues : O, S-bis (α-N-benzyloxycarbonyl-aminoacyl) thiamine (VIII) or O, S-bis (α-N-t-butyloxycarbonylaminoacyl) thiamine (X). O, S-Bis (α-aminoacyl) thiamine trihydrochloride (XI·3HCl) was obtained in good yield by the treatment of X with hydrogen chloride in ethyl acetate at -10°. Thiamine activities of VIII·HCl and XI·3HCl in thiamine deficient rats were similar to those of equimolar thiamine chloride hydrochloride (I-Cl·HCl).</description><subject>Animals</subject><subject>Male</subject><subject>Methods</subject><subject>Rats</subject><subject>Thiamine - analogs & derivatives</subject><subject>Thiamine - chemical synthesis</subject><subject>Thiamine - therapeutic use</subject><subject>Thiamine Deficiency - drug therapy</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1976</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpNkMtO3DAYhS1URIfLhn0lrypAZOr4ksTspqNykZCQynRtOc5vYpTLEHtU5bF4EZ6pTmdo2fwXnXO-xUHoNCXzlPLim1mXc8rnhaB7aJYynieCUvYJzQghMqEsY5_RoffPhFBBcnaADlJCU5rJGWpXNeCfoE1wfYd7ix-TReu6voVQj02onY4f4N8u1HhhXIUXXT1Wg6sAX-Ep-zh2oQbv_BR-uIz57_E-e3tNpmSvzdic43fOMdq3uvFwsttH6Nf1j9XyNrl_uLlbLu4TwzkPSUmssQXLoRBAjNCWSVIJmRMpeS5pCaW11AjLS2Z1IVguS1llpU6ZzDJaFOwIfd1y10P_sgEfVOu8gabRHfQbryKbZpSwaLzYGs3Qez-AVevBtXoYVUrU1K2K3SrKVew2mr_sqJuyheqD9W-ZUV9u9Wcf9BP80_UQnGlgQqVSFBNObEek_ldrPSjo2B-VHIw9</recordid><startdate>19760101</startdate><enddate>19760101</enddate><creator>YASUO, HARUNORI</creator><creator>YONEDA, NAOTO</creator><creator>MATSUOKA, YUZO</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>19760101</creationdate><title>The Reaction of S-Aminomethylthiamine with Acid Anhydride : The Synthesis of O, S-Bis (α-aminoacyl) thiamine</title><author>YASUO, HARUNORI ; YONEDA, NAOTO ; MATSUOKA, YUZO</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c444t-b0fcf837e85e0c5af390d5970994792bebff2c5f4b3fa85379b9d6ba139662883</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1976</creationdate><topic>Animals</topic><topic>Male</topic><topic>Methods</topic><topic>Rats</topic><topic>Thiamine - analogs & derivatives</topic><topic>Thiamine - chemical synthesis</topic><topic>Thiamine - therapeutic use</topic><topic>Thiamine Deficiency - drug therapy</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>YASUO, HARUNORI</creatorcontrib><creatorcontrib>YONEDA, NAOTO</creatorcontrib><creatorcontrib>MATSUOKA, YUZO</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>YASUO, HARUNORI</au><au>YONEDA, NAOTO</au><au>MATSUOKA, YUZO</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>The Reaction of S-Aminomethylthiamine with Acid Anhydride : The Synthesis of O, S-Bis (α-aminoacyl) thiamine</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>1976-01-01</date><risdate>1976</risdate><volume>24</volume><issue>5</issue><spage>852</spage><epage>858</epage><pages>852-858</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><abstract>It was found that the reaction of S-aminomethylthiamine (II) with acid anhydride afforded the corresponding S-acylthiamine (III) or, O, S-diacylthiamine (IV). Furthermore the reaction of II with anhydrides (VII, IX, XII) of N-benzyloxycarbonyl-or N-t-butyloxycarbonyl-L-amino acid in tetrahydrofuran at -5-5° gave successfully the novel thiamine compounds with amino acid residues : O, S-bis (α-N-benzyloxycarbonyl-aminoacyl) thiamine (VIII) or O, S-bis (α-N-t-butyloxycarbonylaminoacyl) thiamine (X). O, S-Bis (α-aminoacyl) thiamine trihydrochloride (XI·3HCl) was obtained in good yield by the treatment of X with hydrogen chloride in ethyl acetate at -10°. Thiamine activities of VIII·HCl and XI·3HCl in thiamine deficient rats were similar to those of equimolar thiamine chloride hydrochloride (I-Cl·HCl).</abstract><cop>Japan</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>1021269</pmid><doi>10.1248/cpb.24.852</doi><tpages>7</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0009-2363 |
| ispartof | Chemical and Pharmaceutical Bulletin, 1976/05/25, Vol.24(5), pp.852-858 |
| issn | 0009-2363 1347-5223 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_83726203 |
| source | J-STAGE Free; MEDLINE; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; Free Full-Text Journals in Chemistry |
| subjects | Animals Male Methods Rats Thiamine - analogs & derivatives Thiamine - chemical synthesis Thiamine - therapeutic use Thiamine Deficiency - drug therapy |
| title | The Reaction of S-Aminomethylthiamine with Acid Anhydride : The Synthesis of O, S-Bis (α-aminoacyl) thiamine |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-06T02%3A18%3A21IST&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=The%20Reaction%20of%20S-Aminomethylthiamine%20with%20Acid%20Anhydride%20:%20The%20Synthesis%20of%20O,%20S-Bis%20(%CE%B1-aminoacyl)%20thiamine&rft.jtitle=Chemical%20&%20pharmaceutical%20bulletin&rft.au=YASUO,%20HARUNORI&rft.date=1976-01-01&rft.volume=24&rft.issue=5&rft.spage=852&rft.epage=858&rft.pages=852-858&rft.issn=0009-2363&rft.eissn=1347-5223&rft_id=info:doi/10.1248/cpb.24.852&rft_dat=%3Cproquest_cross%3E83726203%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=83726203&rft_id=info:pmid/1021269&rfr_iscdi=true |