Enantiomeric 3-hydroxypent-4-enethionamides from thioglucosides of Crambe and Brassica seeds by action of ferrous salts
epi-Progoitrin, the major thioglucoside of Crambe abyssinica seed, is cleaved by ferrous salts to yield (S)-1-cyano-2-hydroxy-3-butene and (S)-3-hydroxypent-4-enethionamide. The products are the same whether obtained from the purified thioglucoside or from the seed meal. Identical behavior was obser...
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| Veröffentlicht in: | Canadian journal of chemistry 1968-05, Vol.46 (9), p.1507-1512 |
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| container_title | Canadian journal of chemistry |
| container_volume | 46 |
| creator | Austin, F. L Gent, C. A Wolff, I. A |
| description | epi-Progoitrin, the major thioglucoside of Crambe abyssinica seed, is cleaved by ferrous salts to yield (S)-1-cyano-2-hydroxy-3-butene and (S)-3-hydroxypent-4-enethionamide. The products are the same whether obtained from the purified thioglucoside or from the seed meal. Identical behavior was observed for seed meal of Brassica napus, which gave corresponding derivatives of the opposite configuration. Optical rotatory dispersion and proton magnetic resonance studies suggest the existence of solvent-dependent differences in rotamer composition for the 3-hydroxypent-4-enethionamides. |
| doi_str_mv | 10.1139/v68-247 |
| format | Article |
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L ; Gent, C. A ; Wolff, I. A</creator><creatorcontrib>Austin, F. L ; Gent, C. A ; Wolff, I. A</creatorcontrib><description>epi-Progoitrin, the major thioglucoside of Crambe abyssinica seed, is cleaved by ferrous salts to yield (S)-1-cyano-2-hydroxy-3-butene and (S)-3-hydroxypent-4-enethionamide. The products are the same whether obtained from the purified thioglucoside or from the seed meal. Identical behavior was observed for seed meal of Brassica napus, which gave corresponding derivatives of the opposite configuration. Optical rotatory dispersion and proton magnetic resonance studies suggest the existence of solvent-dependent differences in rotamer composition for the 3-hydroxypent-4-enethionamides.</description><identifier>ISSN: 0008-4042</identifier><identifier>EISSN: 1480-3291</identifier><identifier>DOI: 10.1139/v68-247</identifier><language>eng</language><publisher>Ottawa, Canada: NRC Research Press</publisher><ispartof>Canadian journal of chemistry, 1968-05, Vol.46 (9), p.1507-1512</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c136f-9b9150fe8114959290fc74c5d4e7f3650a7b65b43ddd3533df77f12b362367c3</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://cdnsciencepub.com/doi/pdf/10.1139/v68-247$$EPDF$$P50$$Gnrcresearch$$H</linktopdf><linktohtml>$$Uhttps://cdnsciencepub.com/doi/full/10.1139/v68-247$$EHTML$$P50$$Gnrcresearch$$H</linktohtml><link.rule.ids>314,776,780,2919,27901,27902,64401,64979</link.rule.ids></links><search><creatorcontrib>Austin, F. L</creatorcontrib><creatorcontrib>Gent, C. A</creatorcontrib><creatorcontrib>Wolff, I. A</creatorcontrib><title>Enantiomeric 3-hydroxypent-4-enethionamides from thioglucosides of Crambe and Brassica seeds by action of ferrous salts</title><title>Canadian journal of chemistry</title><addtitle>Revue canadienne de chimie</addtitle><description>epi-Progoitrin, the major thioglucoside of Crambe abyssinica seed, is cleaved by ferrous salts to yield (S)-1-cyano-2-hydroxy-3-butene and (S)-3-hydroxypent-4-enethionamide. The products are the same whether obtained from the purified thioglucoside or from the seed meal. Identical behavior was observed for seed meal of Brassica napus, which gave corresponding derivatives of the opposite configuration. Optical rotatory dispersion and proton magnetic resonance studies suggest the existence of solvent-dependent differences in rotamer composition for the 3-hydroxypent-4-enethionamides.</description><issn>0008-4042</issn><issn>1480-3291</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1968</creationdate><recordtype>article</recordtype><recordid>eNp90F9LwzAUBfAgCs4pfoU8KQjRpEmb9lHH_AMDX_Ze0uTGVdZk5HZqv_06t1d9utzDj_NwCLkW_F4IWT18FSXLlD4hE6FKzmRWiVMy4ZyXTHGVnZMLxM_x1TzLJ-R7Hkzo29hBai2VbDW4FH-GDYSeKQYB-lUbg-laB0h9ih3dBx_rrY34m0VPZ8l0DVATHH1KBrG1hiKAQ9oM1NixPeyZh5TiFimadY-X5MybNcLV8U7J8nm-nL2yxfvL2-xxwayQhWdVU4mceyiFUFVeZRX3ViubOwXayyLnRjdF3ijpnJO5lM5r7UXWyCKThbZySm4PtTZFxAS-3qS2M2moBa_3c9XjXPU41yjvDjIkmwDBJLv6B9_8jY-o3jgvd3tvekY</recordid><startdate>19680501</startdate><enddate>19680501</enddate><creator>Austin, F. L</creator><creator>Gent, C. A</creator><creator>Wolff, I. A</creator><general>NRC Research Press</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>19680501</creationdate><title>Enantiomeric 3-hydroxypent-4-enethionamides from thioglucosides of Crambe and Brassica seeds by action of ferrous salts</title><author>Austin, F. L ; Gent, C. A ; Wolff, I. A</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c136f-9b9150fe8114959290fc74c5d4e7f3650a7b65b43ddd3533df77f12b362367c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1968</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Austin, F. L</creatorcontrib><creatorcontrib>Gent, C. A</creatorcontrib><creatorcontrib>Wolff, I. A</creatorcontrib><collection>CrossRef</collection><jtitle>Canadian journal of chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Austin, F. L</au><au>Gent, C. A</au><au>Wolff, I. A</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enantiomeric 3-hydroxypent-4-enethionamides from thioglucosides of Crambe and Brassica seeds by action of ferrous salts</atitle><jtitle>Canadian journal of chemistry</jtitle><addtitle>Revue canadienne de chimie</addtitle><date>1968-05-01</date><risdate>1968</risdate><volume>46</volume><issue>9</issue><spage>1507</spage><epage>1512</epage><pages>1507-1512</pages><issn>0008-4042</issn><eissn>1480-3291</eissn><abstract>epi-Progoitrin, the major thioglucoside of Crambe abyssinica seed, is cleaved by ferrous salts to yield (S)-1-cyano-2-hydroxy-3-butene and (S)-3-hydroxypent-4-enethionamide. The products are the same whether obtained from the purified thioglucoside or from the seed meal. Identical behavior was observed for seed meal of Brassica napus, which gave corresponding derivatives of the opposite configuration. Optical rotatory dispersion and proton magnetic resonance studies suggest the existence of solvent-dependent differences in rotamer composition for the 3-hydroxypent-4-enethionamides.</abstract><cop>Ottawa, Canada</cop><pub>NRC Research Press</pub><doi>10.1139/v68-247</doi><tpages>6</tpages></addata></record> |
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| language | eng |
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| source | NRC Research Press; EZB-FREE-00999 freely available EZB journals; Free Full-Text Journals in Chemistry |
| title | Enantiomeric 3-hydroxypent-4-enethionamides from thioglucosides of Crambe and Brassica seeds by action of ferrous salts |
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