Resolution of the enantiomers of various α-substituted ornithine and lysine analogs by high-performance liquid chromatography with chiral eluant and by gas chromatography on Chirasil-Val
A reversed-phase high-performance liquid chromatography method, with l-proline and copper as chiral mobile phase, is described for the enantiomeric resolution of various α-substituted ornithine and lysine analogs. Although ornithine gives no separation with the chiral eluant used, excellent resoluti...
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| Veröffentlicht in: | Analytical biochemistry 1987-07, Vol.164 (1), p.102-116 |
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| creator | Wagner, J. Gaget, C. Heintzelmann, B. Wolf, E. |
| description | A reversed-phase high-performance liquid chromatography method, with
l-proline and copper as chiral mobile phase, is described for the enantiomeric resolution of various α-substituted ornithine and lysine analogs. Although ornithine gives no separation with the chiral eluant used, excellent resolutions are obtained for various α-alkyl-, α-halogenomethyl-, α-vinyl-, and α-ethynyl-substituted ornithines. Similar separations are also observed for the dehydroornithine and lysine analogs. Gas chromatography on a chiral stationary phase, Chirasil-Val, allows the resolution of the ornithine and lysine analogs after derivatization into the monofluoroacyl derivatives of their corresponding lactams. No resolution or only a poor resolution is obtained by GC on Chirasil-Val for the dehydroornithine analogs as their di-
N-perfluoroacyl alkyl esters. The chiral eluant HPLC procedure is easily scaled up for the semipreparative resolution of several ornithine analogs, i.e., α-fluoromethylornithine, α-difluoromethylornithine, α-chlorofluoromethylornithine, and α-fluoromethyldehydroornithine, which are known as potent ornithine decarboxylase inhibitors
in vitro and
in vivo. |
| doi_str_mv | 10.1016/0003-2697(87)90374-5 |
| format | Article |
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l-proline and copper as chiral mobile phase, is described for the enantiomeric resolution of various α-substituted ornithine and lysine analogs. Although ornithine gives no separation with the chiral eluant used, excellent resolutions are obtained for various α-alkyl-, α-halogenomethyl-, α-vinyl-, and α-ethynyl-substituted ornithines. Similar separations are also observed for the dehydroornithine and lysine analogs. Gas chromatography on a chiral stationary phase, Chirasil-Val, allows the resolution of the ornithine and lysine analogs after derivatization into the monofluoroacyl derivatives of their corresponding lactams. No resolution or only a poor resolution is obtained by GC on Chirasil-Val for the dehydroornithine analogs as their di-
N-perfluoroacyl alkyl esters. The chiral eluant HPLC procedure is easily scaled up for the semipreparative resolution of several ornithine analogs, i.e., α-fluoromethylornithine, α-difluoromethylornithine, α-chlorofluoromethylornithine, and α-fluoromethyldehydroornithine, which are known as potent ornithine decarboxylase inhibitors
in vitro and
in vivo.</description><identifier>ISSN: 0003-2697</identifier><identifier>EISSN: 1096-0309</identifier><identifier>DOI: 10.1016/0003-2697(87)90374-5</identifier><identifier>PMID: 3118732</identifier><identifier>CODEN: ANBCA2</identifier><language>eng</language><publisher>San Diego, CA: Elsevier Inc</publisher><subject><![CDATA[Aminoacids, peptides. Hormones. Neuropeptides ; Analytical, structural and metabolic biochemistry ; Biological and medical sciences ; chromatographic resolution of enantiomers ; Chromatography, Gas ; Chromatography, High Pressure Liquid ; Copper ; Eflornithine - analogs & derivatives ; Eflornithine - isolation & purification ; Fundamental and applied biological sciences. Psychology ; GC with chiral stationary phase ; HPLC with chiral eluants ; Indicators and Reagents ; lysine ; Lysine - analogs & derivatives ; Lysine - isolation & purification ; lysine analogs ; Organic Chemicals ; ornithine ; Ornithine - analogs & derivatives ; Ornithine - isolation & purification ; Ornithine Decarboxylase Inhibitors ; Proteins ; resolution of amino acids ; Stereoisomerism]]></subject><ispartof>Analytical biochemistry, 1987-07, Vol.164 (1), p.102-116</ispartof><rights>1987</rights><rights>1988 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c417t-77f13fcb52a9b3e609b1d14c2089b7ed7797691481f2a564824225fa8899441e3</citedby><cites>FETCH-LOGICAL-c417t-77f13fcb52a9b3e609b1d14c2089b7ed7797691481f2a564824225fa8899441e3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/0003-2697(87)90374-5$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=7658785$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/3118732$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Wagner, J.</creatorcontrib><creatorcontrib>Gaget, C.</creatorcontrib><creatorcontrib>Heintzelmann, B.</creatorcontrib><creatorcontrib>Wolf, E.</creatorcontrib><title>Resolution of the enantiomers of various α-substituted ornithine and lysine analogs by high-performance liquid chromatography with chiral eluant and by gas chromatography on Chirasil-Val</title><title>Analytical biochemistry</title><addtitle>Anal Biochem</addtitle><description>A reversed-phase high-performance liquid chromatography method, with
l-proline and copper as chiral mobile phase, is described for the enantiomeric resolution of various α-substituted ornithine and lysine analogs. Although ornithine gives no separation with the chiral eluant used, excellent resolutions are obtained for various α-alkyl-, α-halogenomethyl-, α-vinyl-, and α-ethynyl-substituted ornithines. Similar separations are also observed for the dehydroornithine and lysine analogs. Gas chromatography on a chiral stationary phase, Chirasil-Val, allows the resolution of the ornithine and lysine analogs after derivatization into the monofluoroacyl derivatives of their corresponding lactams. No resolution or only a poor resolution is obtained by GC on Chirasil-Val for the dehydroornithine analogs as their di-
N-perfluoroacyl alkyl esters. The chiral eluant HPLC procedure is easily scaled up for the semipreparative resolution of several ornithine analogs, i.e., α-fluoromethylornithine, α-difluoromethylornithine, α-chlorofluoromethylornithine, and α-fluoromethyldehydroornithine, which are known as potent ornithine decarboxylase inhibitors
in vitro and
in vivo.</description><subject>Aminoacids, peptides. Hormones. Neuropeptides</subject><subject>Analytical, structural and metabolic biochemistry</subject><subject>Biological and medical sciences</subject><subject>chromatographic resolution of enantiomers</subject><subject>Chromatography, Gas</subject><subject>Chromatography, High Pressure Liquid</subject><subject>Copper</subject><subject>Eflornithine - analogs & derivatives</subject><subject>Eflornithine - isolation & purification</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>GC with chiral stationary phase</subject><subject>HPLC with chiral eluants</subject><subject>Indicators and Reagents</subject><subject>lysine</subject><subject>Lysine - analogs & derivatives</subject><subject>Lysine - isolation & purification</subject><subject>lysine analogs</subject><subject>Organic Chemicals</subject><subject>ornithine</subject><subject>Ornithine - analogs & derivatives</subject><subject>Ornithine - isolation & purification</subject><subject>Ornithine Decarboxylase Inhibitors</subject><subject>Proteins</subject><subject>resolution of amino acids</subject><subject>Stereoisomerism</subject><issn>0003-2697</issn><issn>1096-0309</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1987</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkc-u1CAUxonRXMerb6AJC2N0UYWWFtiYmIn_kpuYGHVLKD1MMbTMBXrNPJZr38Fnkt6ZzMKFroBzfufj5PsQekzJS0po94oQ0lR1J_lzwV9I0nBWtXfQhhLZVaQh8i7anJH76EFK3wmhlLXdBbpoKBW8qTfo12dIwS_ZhRkHi_MIGGY9l_cEMa2lGx1dWBL-_bNKS5-yy0uGAYc4uzy6GbCeB-wP6XjVPuwS7g94dLux2kO0IU56NoC9u17cgM0Yw6Rz2EW9Hw_4RxEpNRe1x-CX8vOtXhHY6fQ3XHbcrmhyvvqm_UN0z2qf4NHpvERf3739sv1QXX16_3H75qoyjPJccW5pY03f1lr2DXRE9nSgzNREyJ7DwLnknaRMUFvrtmOiZnXdWi2ElIxRaC7Rs6PuPobrBVJWk0sGvNczFGeUKJYLVqz-H0iZJIKKuoDsCJoYUopg1T66SceDokSt4ao1ObUmpwRXt-Gqtow9Oekv_QTDeeiUZuk_PfV1MtrbWIx36YzxrhVcrDKvjxgU024cRJWMg5LR4CKYrIbg_r3HHzV_xNw</recordid><startdate>19870701</startdate><enddate>19870701</enddate><creator>Wagner, J.</creator><creator>Gaget, C.</creator><creator>Heintzelmann, B.</creator><creator>Wolf, E.</creator><general>Elsevier Inc</general><general>Elsevier</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>7QL</scope><scope>C1K</scope><scope>7X8</scope></search><sort><creationdate>19870701</creationdate><title>Resolution of the enantiomers of various α-substituted ornithine and lysine analogs by high-performance liquid chromatography with chiral eluant and by gas chromatography on Chirasil-Val</title><author>Wagner, J. ; Gaget, C. ; Heintzelmann, B. ; Wolf, E.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c417t-77f13fcb52a9b3e609b1d14c2089b7ed7797691481f2a564824225fa8899441e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1987</creationdate><topic>Aminoacids, peptides. Hormones. Neuropeptides</topic><topic>Analytical, structural and metabolic biochemistry</topic><topic>Biological and medical sciences</topic><topic>chromatographic resolution of enantiomers</topic><topic>Chromatography, Gas</topic><topic>Chromatography, High Pressure Liquid</topic><topic>Copper</topic><topic>Eflornithine - analogs & derivatives</topic><topic>Eflornithine - isolation & purification</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>GC with chiral stationary phase</topic><topic>HPLC with chiral eluants</topic><topic>Indicators and Reagents</topic><topic>lysine</topic><topic>Lysine - analogs & derivatives</topic><topic>Lysine - isolation & purification</topic><topic>lysine analogs</topic><topic>Organic Chemicals</topic><topic>ornithine</topic><topic>Ornithine - analogs & derivatives</topic><topic>Ornithine - isolation & purification</topic><topic>Ornithine Decarboxylase Inhibitors</topic><topic>Proteins</topic><topic>resolution of amino acids</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wagner, J.</creatorcontrib><creatorcontrib>Gaget, C.</creatorcontrib><creatorcontrib>Heintzelmann, B.</creatorcontrib><creatorcontrib>Wolf, E.</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>Bacteriology Abstracts (Microbiology B)</collection><collection>Environmental Sciences and Pollution Management</collection><collection>MEDLINE - Academic</collection><jtitle>Analytical biochemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wagner, J.</au><au>Gaget, C.</au><au>Heintzelmann, B.</au><au>Wolf, E.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Resolution of the enantiomers of various α-substituted ornithine and lysine analogs by high-performance liquid chromatography with chiral eluant and by gas chromatography on Chirasil-Val</atitle><jtitle>Analytical biochemistry</jtitle><addtitle>Anal Biochem</addtitle><date>1987-07-01</date><risdate>1987</risdate><volume>164</volume><issue>1</issue><spage>102</spage><epage>116</epage><pages>102-116</pages><issn>0003-2697</issn><eissn>1096-0309</eissn><coden>ANBCA2</coden><abstract>A reversed-phase high-performance liquid chromatography method, with
l-proline and copper as chiral mobile phase, is described for the enantiomeric resolution of various α-substituted ornithine and lysine analogs. Although ornithine gives no separation with the chiral eluant used, excellent resolutions are obtained for various α-alkyl-, α-halogenomethyl-, α-vinyl-, and α-ethynyl-substituted ornithines. Similar separations are also observed for the dehydroornithine and lysine analogs. Gas chromatography on a chiral stationary phase, Chirasil-Val, allows the resolution of the ornithine and lysine analogs after derivatization into the monofluoroacyl derivatives of their corresponding lactams. No resolution or only a poor resolution is obtained by GC on Chirasil-Val for the dehydroornithine analogs as their di-
N-perfluoroacyl alkyl esters. The chiral eluant HPLC procedure is easily scaled up for the semipreparative resolution of several ornithine analogs, i.e., α-fluoromethylornithine, α-difluoromethylornithine, α-chlorofluoromethylornithine, and α-fluoromethyldehydroornithine, which are known as potent ornithine decarboxylase inhibitors
in vitro and
in vivo.</abstract><cop>San Diego, CA</cop><pub>Elsevier Inc</pub><pmid>3118732</pmid><doi>10.1016/0003-2697(87)90374-5</doi><tpages>15</tpages></addata></record> |
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| ispartof | Analytical biochemistry, 1987-07, Vol.164 (1), p.102-116 |
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| subjects | Aminoacids, peptides. Hormones. Neuropeptides Analytical, structural and metabolic biochemistry Biological and medical sciences chromatographic resolution of enantiomers Chromatography, Gas Chromatography, High Pressure Liquid Copper Eflornithine - analogs & derivatives Eflornithine - isolation & purification Fundamental and applied biological sciences. Psychology GC with chiral stationary phase HPLC with chiral eluants Indicators and Reagents lysine Lysine - analogs & derivatives Lysine - isolation & purification lysine analogs Organic Chemicals ornithine Ornithine - analogs & derivatives Ornithine - isolation & purification Ornithine Decarboxylase Inhibitors Proteins resolution of amino acids Stereoisomerism |
| title | Resolution of the enantiomers of various α-substituted ornithine and lysine analogs by high-performance liquid chromatography with chiral eluant and by gas chromatography on Chirasil-Val |
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