Diastereoselective synthesis, binding affinity for vitamin D receptor, and chiral stationary phase chromatography of hydroxy analogs of 1,25-dihydroxycholecalciferol and 25-hydroxycholecalciferol
A series of analogs of 1,25‐dihydroxycholecalciferol and 25‐hydroxycholecalciferol were obtained with an additional hydroxyl in the aliphatic side chain at carbon atom C‐24. These analogs were synthesized by direct and diastereo‐selective α‐hydroxylation of enolates derived from respective vitamin D...
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| Veröffentlicht in: | Chirality (New York, N.Y.) N.Y.), 1999, Vol.11 (9), p.701-706 |
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| container_title | Chirality (New York, N.Y.) |
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| creator | Odrzywolska, Małgorzata Chodyński, Michał Zorgdrager, Jan Van De Velde, Jan-Paul Kutner, Andrzej |
| description | A series of analogs of 1,25‐dihydroxycholecalciferol and 25‐hydroxycholecalciferol were obtained with an additional hydroxyl in the aliphatic side chain at carbon atom C‐24. These analogs were synthesized by direct and diastereo‐selective α‐hydroxylation of enolates derived from respective vitamin D esters using Davies chiral oxaziridines. The use of (+)‐(2R,8aS)‐(8,8‐dichlorocamphoryl)sulfonyl oxaziridine resulted in (R) stereochemistry of the new asymmetric center for both series of analogs. Similarly, (−)‐(2S,8aR) oxaziridine gave (S) analogs. The diastereomeric purity of hydroxy analogs was determined by high‐performance liquid chromatography on a chiral stationary phase. High diastereopurity of hydroxylation of vitamin D esters was obtained without the use of any chiral auxiliary. The binding affinity of (24R)‐1,24,25‐trihydroxycholecalciferol for the calf thymus intracellular vitamin D receptor was one order of magnitude higher than that of the respective (24S)‐diastereomer. Chirality 11:701–706, 1999. © 1999 Wiley‐Liss, Inc. |
| doi_str_mv | 10.1002/(SICI)1520-636X(1999)11:9<701::AID-CHIR6>3.0.CO;2-L |
| format | Article |
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These analogs were synthesized by direct and diastereo‐selective α‐hydroxylation of enolates derived from respective vitamin D esters using Davies chiral oxaziridines. The use of (+)‐(2R,8aS)‐(8,8‐dichlorocamphoryl)sulfonyl oxaziridine resulted in (R) stereochemistry of the new asymmetric center for both series of analogs. Similarly, (−)‐(2S,8aR) oxaziridine gave (S) analogs. The diastereomeric purity of hydroxy analogs was determined by high‐performance liquid chromatography on a chiral stationary phase. High diastereopurity of hydroxylation of vitamin D esters was obtained without the use of any chiral auxiliary. The binding affinity of (24R)‐1,24,25‐trihydroxycholecalciferol for the calf thymus intracellular vitamin D receptor was one order of magnitude higher than that of the respective (24S)‐diastereomer. Chirality 11:701–706, 1999. © 1999 Wiley‐Liss, Inc.</description><identifier>ISSN: 0899-0042</identifier><identifier>EISSN: 1520-636X</identifier><identifier>DOI: 10.1002/(SICI)1520-636X(1999)11:9<701::AID-CHIR6>3.0.CO;2-L</identifier><identifier>PMID: 10506431</identifier><language>eng</language><publisher>New York: John Wiley & Sons, Inc</publisher><subject>(24R)-1 ; (24R)-24 ; (24R)‐1,24,25‐ and (24S)‐1,24,25‐trihydroxycholecalciferols ; (24R)‐24,25‐ and (24S),24,25‐dihydroxycholecalciferols ; 25- and (24S) ; 25- and (24S)-1 ; 25-dihydroxycholecalciferols ; 25-trihydroxycholecalciferols ; Animals ; binding affinity for vitamin D receptor ; Calcifediol - chemical synthesis ; Calcifediol - isolation & purification ; Calcifediol - metabolism ; Calcitriol - chemical synthesis ; Calcitriol - isolation & purification ; Calcitriol - metabolism ; Cattle ; chiral stationary phase HPLC ; Chromatography, High Pressure Liquid - methods ; diastereoselective α-hydroxylation ; Magnetic Resonance Spectroscopy ; Protein Binding ; Receptors, Calcitriol - metabolism ; Stereoisomerism</subject><ispartof>Chirality (New York, N.Y.), 1999, Vol.11 (9), p.701-706</ispartof><rights>Copyright © 1999 Wiley‐Liss, Inc.</rights><rights>Copyright 1999 Wiley-Liss, Inc.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c3796-2de25c1882e763e77f27dc92ef0de5e0b400ae087656976e984b060f672964dd3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2F%28SICI%291520-636X%281999%2911%3A9%3C701%3A%3AAID-CHIR6%3E3.0.CO%3B2-L$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2F%28SICI%291520-636X%281999%2911%3A9%3C701%3A%3AAID-CHIR6%3E3.0.CO%3B2-L$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,4024,27923,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/10506431$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Odrzywolska, Małgorzata</creatorcontrib><creatorcontrib>Chodyński, Michał</creatorcontrib><creatorcontrib>Zorgdrager, Jan</creatorcontrib><creatorcontrib>Van De Velde, Jan-Paul</creatorcontrib><creatorcontrib>Kutner, Andrzej</creatorcontrib><title>Diastereoselective synthesis, binding affinity for vitamin D receptor, and chiral stationary phase chromatography of hydroxy analogs of 1,25-dihydroxycholecalciferol and 25-hydroxycholecalciferol</title><title>Chirality (New York, N.Y.)</title><addtitle>Chirality</addtitle><description>A series of analogs of 1,25‐dihydroxycholecalciferol and 25‐hydroxycholecalciferol were obtained with an additional hydroxyl in the aliphatic side chain at carbon atom C‐24. These analogs were synthesized by direct and diastereo‐selective α‐hydroxylation of enolates derived from respective vitamin D esters using Davies chiral oxaziridines. The use of (+)‐(2R,8aS)‐(8,8‐dichlorocamphoryl)sulfonyl oxaziridine resulted in (R) stereochemistry of the new asymmetric center for both series of analogs. Similarly, (−)‐(2S,8aR) oxaziridine gave (S) analogs. The diastereomeric purity of hydroxy analogs was determined by high‐performance liquid chromatography on a chiral stationary phase. High diastereopurity of hydroxylation of vitamin D esters was obtained without the use of any chiral auxiliary. The binding affinity of (24R)‐1,24,25‐trihydroxycholecalciferol for the calf thymus intracellular vitamin D receptor was one order of magnitude higher than that of the respective (24S)‐diastereomer. Chirality 11:701–706, 1999. © 1999 Wiley‐Liss, Inc.</description><subject>(24R)-1</subject><subject>(24R)-24</subject><subject>(24R)‐1,24,25‐ and (24S)‐1,24,25‐trihydroxycholecalciferols</subject><subject>(24R)‐24,25‐ and (24S),24,25‐dihydroxycholecalciferols</subject><subject>25- and (24S)</subject><subject>25- and (24S)-1</subject><subject>25-dihydroxycholecalciferols</subject><subject>25-trihydroxycholecalciferols</subject><subject>Animals</subject><subject>binding affinity for vitamin D receptor</subject><subject>Calcifediol - chemical synthesis</subject><subject>Calcifediol - isolation & purification</subject><subject>Calcifediol - metabolism</subject><subject>Calcitriol - chemical synthesis</subject><subject>Calcitriol - isolation & purification</subject><subject>Calcitriol - metabolism</subject><subject>Cattle</subject><subject>chiral stationary phase HPLC</subject><subject>Chromatography, High Pressure Liquid - methods</subject><subject>diastereoselective α-hydroxylation</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Protein Binding</subject><subject>Receptors, Calcitriol - metabolism</subject><subject>Stereoisomerism</subject><issn>0899-0042</issn><issn>1520-636X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1999</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9ktFu0zAUhiMEYmXwCshXaJOacuwkdt0hpCmFrlKhwIbgznKTk9YjjYudjuX5eDGSpZqQmLiydM7v77fyJQjOKIwoAHt9cjlP56c0YRDyiH8_oVLKU0on8o0AOpmcz6dhejH_wt9GIxilyzMWLh4Fg_v842AAYylDgJgdBc-8vwYAyaP4aXBEIQEeR3QQ_J4a7Wt0aD2WmNXmBolvqnqD3vghWZkqN9Wa6KIwlakbUlhHbkytt6YiU-Iww11t3ZDoKifZxjhdEl_r2thKu4bsNtpjO3d2q2u7dnq3aYgtyKbJnb1t2lu6tGvfjeiQJWFuDptsY9vX6DIzBTpb3uHb_cPb58GTQpceXxzO4-Dr-3dX6UW4WM7m6fkizCIhechyZElGx2OGgkcoRMFEnkmGBeSYIKxiAI0wFjzhUnCU43gFHAoumORxnkfHwaueu3P25x59rbbGZ1iWukK790qAEIJKaIOXfTBz1nuHhdo5s20_iKKgOrdKdW5V50p1rlTnVlGqZAuhSrVu1Z1bFSlQ6VIxtWipLw_1-9UW87-Yvcw2cNUHfpkSm386_1v5UGM_aLFhjzXtj3J7j9Xuh-IiEon69nGm6AcmZ9NPTH2O_gAZSNNi</recordid><startdate>1999</startdate><enddate>1999</enddate><creator>Odrzywolska, Małgorzata</creator><creator>Chodyński, Michał</creator><creator>Zorgdrager, Jan</creator><creator>Van De Velde, Jan-Paul</creator><creator>Kutner, Andrzej</creator><general>John Wiley & Sons, Inc</general><scope>BSCLL</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>7X8</scope></search><sort><creationdate>1999</creationdate><title>Diastereoselective synthesis, binding affinity for vitamin D receptor, and chiral stationary phase chromatography of hydroxy analogs of 1,25-dihydroxycholecalciferol and 25-hydroxycholecalciferol</title><author>Odrzywolska, Małgorzata ; Chodyński, Michał ; Zorgdrager, Jan ; Van De Velde, Jan-Paul ; Kutner, Andrzej</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3796-2de25c1882e763e77f27dc92ef0de5e0b400ae087656976e984b060f672964dd3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1999</creationdate><topic>(24R)-1</topic><topic>(24R)-24</topic><topic>(24R)‐1,24,25‐ and (24S)‐1,24,25‐trihydroxycholecalciferols</topic><topic>(24R)‐24,25‐ and (24S),24,25‐dihydroxycholecalciferols</topic><topic>25- and (24S)</topic><topic>25- and (24S)-1</topic><topic>25-dihydroxycholecalciferols</topic><topic>25-trihydroxycholecalciferols</topic><topic>Animals</topic><topic>binding affinity for vitamin D receptor</topic><topic>Calcifediol - chemical synthesis</topic><topic>Calcifediol - isolation & purification</topic><topic>Calcifediol - metabolism</topic><topic>Calcitriol - chemical synthesis</topic><topic>Calcitriol - isolation & purification</topic><topic>Calcitriol - metabolism</topic><topic>Cattle</topic><topic>chiral stationary phase HPLC</topic><topic>Chromatography, High Pressure Liquid - methods</topic><topic>diastereoselective α-hydroxylation</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Protein Binding</topic><topic>Receptors, Calcitriol - metabolism</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Odrzywolska, Małgorzata</creatorcontrib><creatorcontrib>Chodyński, Michał</creatorcontrib><creatorcontrib>Zorgdrager, Jan</creatorcontrib><creatorcontrib>Van De Velde, Jan-Paul</creatorcontrib><creatorcontrib>Kutner, Andrzej</creatorcontrib><collection>Istex</collection><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>Chirality (New York, N.Y.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Odrzywolska, Małgorzata</au><au>Chodyński, Michał</au><au>Zorgdrager, Jan</au><au>Van De Velde, Jan-Paul</au><au>Kutner, Andrzej</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Diastereoselective synthesis, binding affinity for vitamin D receptor, and chiral stationary phase chromatography of hydroxy analogs of 1,25-dihydroxycholecalciferol and 25-hydroxycholecalciferol</atitle><jtitle>Chirality (New York, N.Y.)</jtitle><addtitle>Chirality</addtitle><date>1999</date><risdate>1999</risdate><volume>11</volume><issue>9</issue><spage>701</spage><epage>706</epage><pages>701-706</pages><issn>0899-0042</issn><eissn>1520-636X</eissn><abstract>A series of analogs of 1,25‐dihydroxycholecalciferol and 25‐hydroxycholecalciferol were obtained with an additional hydroxyl in the aliphatic side chain at carbon atom C‐24. These analogs were synthesized by direct and diastereo‐selective α‐hydroxylation of enolates derived from respective vitamin D esters using Davies chiral oxaziridines. The use of (+)‐(2R,8aS)‐(8,8‐dichlorocamphoryl)sulfonyl oxaziridine resulted in (R) stereochemistry of the new asymmetric center for both series of analogs. Similarly, (−)‐(2S,8aR) oxaziridine gave (S) analogs. The diastereomeric purity of hydroxy analogs was determined by high‐performance liquid chromatography on a chiral stationary phase. High diastereopurity of hydroxylation of vitamin D esters was obtained without the use of any chiral auxiliary. The binding affinity of (24R)‐1,24,25‐trihydroxycholecalciferol for the calf thymus intracellular vitamin D receptor was one order of magnitude higher than that of the respective (24S)‐diastereomer. Chirality 11:701–706, 1999. © 1999 Wiley‐Liss, Inc.</abstract><cop>New York</cop><pub>John Wiley & Sons, Inc</pub><pmid>10506431</pmid><doi>10.1002/(SICI)1520-636X(1999)11:9<701::AID-CHIR6>3.0.CO;2-L</doi><tpages>6</tpages></addata></record> |
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| identifier | ISSN: 0899-0042 |
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| subjects | (24R)-1 (24R)-24 (24R)‐1,24,25‐ and (24S)‐1,24,25‐trihydroxycholecalciferols (24R)‐24,25‐ and (24S),24,25‐dihydroxycholecalciferols 25- and (24S) 25- and (24S)-1 25-dihydroxycholecalciferols 25-trihydroxycholecalciferols Animals binding affinity for vitamin D receptor Calcifediol - chemical synthesis Calcifediol - isolation & purification Calcifediol - metabolism Calcitriol - chemical synthesis Calcitriol - isolation & purification Calcitriol - metabolism Cattle chiral stationary phase HPLC Chromatography, High Pressure Liquid - methods diastereoselective α-hydroxylation Magnetic Resonance Spectroscopy Protein Binding Receptors, Calcitriol - metabolism Stereoisomerism |
| title | Diastereoselective synthesis, binding affinity for vitamin D receptor, and chiral stationary phase chromatography of hydroxy analogs of 1,25-dihydroxycholecalciferol and 25-hydroxycholecalciferol |
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