Electrochemical cholesterylation of sugars with cholesteryl diphenylphosphate
Electrochemical reactions of sugars with cholesteryl diphenylphosphate provide different polycholesterylated products. [Display omitted] •Electrochemical reactions of sugars with cholesteryl diphenylphosphate provide glycoconjugates.•The cholesterylation reactions are completely stereoselective.•Pol...
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| Veröffentlicht in: | Steroids 2017-01, Vol.117, p.44-51 |
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| container_title | Steroids |
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| creator | Tomkiel, Aneta M. Siergiejczyk, Leszek Naróg, Dorota Płoszyńska, Jolanta Sobkowiak, Andrzej Morzycki, Jacek W. |
| description | Electrochemical reactions of sugars with cholesteryl diphenylphosphate provide different polycholesterylated products. [Display omitted]
•Electrochemical reactions of sugars with cholesteryl diphenylphosphate provide glycoconjugates.•The cholesterylation reactions are completely stereoselective.•Polyol reactions yield mono-, di-, tri-, or tetra-cholesterylated products.
Electrochemical cholesterylation of various sugars with cholesteryl diphenylphosphate was studied. The reaction afforded mono-, di-, tri-, and tetra-cholesterylated products using equivalent amounts of the reagent. The reactions turned out to be completely stereoselective with respect to both sugar and steroid but only partially regioselective – primary and anomeric hydroxyl groups in sugars were the most reactive ones while no substantial differences in reactivity was found for different secondary hydroxyl groups. |
| doi_str_mv | 10.1016/j.steroids.2016.05.011 |
| format | Article |
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•Electrochemical reactions of sugars with cholesteryl diphenylphosphate provide glycoconjugates.•The cholesterylation reactions are completely stereoselective.•Polyol reactions yield mono-, di-, tri-, or tetra-cholesterylated products.
Electrochemical cholesterylation of various sugars with cholesteryl diphenylphosphate was studied. The reaction afforded mono-, di-, tri-, and tetra-cholesterylated products using equivalent amounts of the reagent. The reactions turned out to be completely stereoselective with respect to both sugar and steroid but only partially regioselective – primary and anomeric hydroxyl groups in sugars were the most reactive ones while no substantial differences in reactivity was found for different secondary hydroxyl groups.</description><identifier>ISSN: 0039-128X</identifier><identifier>EISSN: 1878-5867</identifier><identifier>DOI: 10.1016/j.steroids.2016.05.011</identifier><identifier>PMID: 27263439</identifier><language>eng</language><publisher>United States: Elsevier Inc</publisher><subject>Cholesterol ; Cholesterol - chemistry ; Cholesterol - metabolism ; Cholesteryl diphenylphosphate ; Cholesterylation ; Electrochemical oxidation ; Electrochemistry - methods ; Glycosylation ; Molecular Structure ; Stereoisomerism</subject><ispartof>Steroids, 2017-01, Vol.117, p.44-51</ispartof><rights>2016 Elsevier Inc.</rights><rights>Copyright © 2016 Elsevier Inc. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c438t-38c84f4219e03dd4dd0e475318dd857c51b7cf3a67023420dfd85bd6423755383</citedby><cites>FETCH-LOGICAL-c438t-38c84f4219e03dd4dd0e475318dd857c51b7cf3a67023420dfd85bd6423755383</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.steroids.2016.05.011$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3548,27923,27924,45994</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/27263439$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Tomkiel, Aneta M.</creatorcontrib><creatorcontrib>Siergiejczyk, Leszek</creatorcontrib><creatorcontrib>Naróg, Dorota</creatorcontrib><creatorcontrib>Płoszyńska, Jolanta</creatorcontrib><creatorcontrib>Sobkowiak, Andrzej</creatorcontrib><creatorcontrib>Morzycki, Jacek W.</creatorcontrib><title>Electrochemical cholesterylation of sugars with cholesteryl diphenylphosphate</title><title>Steroids</title><addtitle>Steroids</addtitle><description>Electrochemical reactions of sugars with cholesteryl diphenylphosphate provide different polycholesterylated products. [Display omitted]
•Electrochemical reactions of sugars with cholesteryl diphenylphosphate provide glycoconjugates.•The cholesterylation reactions are completely stereoselective.•Polyol reactions yield mono-, di-, tri-, or tetra-cholesterylated products.
Electrochemical cholesterylation of various sugars with cholesteryl diphenylphosphate was studied. The reaction afforded mono-, di-, tri-, and tetra-cholesterylated products using equivalent amounts of the reagent. The reactions turned out to be completely stereoselective with respect to both sugar and steroid but only partially regioselective – primary and anomeric hydroxyl groups in sugars were the most reactive ones while no substantial differences in reactivity was found for different secondary hydroxyl groups.</description><subject>Cholesterol</subject><subject>Cholesterol - chemistry</subject><subject>Cholesterol - metabolism</subject><subject>Cholesteryl diphenylphosphate</subject><subject>Cholesterylation</subject><subject>Electrochemical oxidation</subject><subject>Electrochemistry - methods</subject><subject>Glycosylation</subject><subject>Molecular Structure</subject><subject>Stereoisomerism</subject><issn>0039-128X</issn><issn>1878-5867</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkE1PwzAMhiMEYmPwF6YeubTks0lvoGl8SENcQOIWdYlLM3VLSVrQ_j2dtiFunCzbr_3aD0JTgjOCSX6zymIHwTsbMzrkGRYZJuQEjYmSKhUql6dojDErUkLV-whdxLjCGOesoOdoRCXNGWfFGD3PGzBd8KaGtTNlk5jaN7DbvW3KzvlN4qsk9h9liMm36-q__cS6tobNtmlrH9u67OASnVVlE-HqECfo7X7-OntMFy8PT7O7RWo4U13KlFG84pQUgJm13FoMXApGlLVKSCPIUpqKlbnElHGKbTWUlzbnlEkhmGITdL3f2wb_2Q_n6LWLBpqm3IDvoyZKFJJgrnbSfC81wccYoNJtcOsybDXBeodSr_QRpd6h1FjoAeUwOD149Ms12N-xI7tBcLsXwPDpl4Ogo3GwMWBdGJhq691_Hj9CW4oP</recordid><startdate>201701</startdate><enddate>201701</enddate><creator>Tomkiel, Aneta M.</creator><creator>Siergiejczyk, Leszek</creator><creator>Naróg, Dorota</creator><creator>Płoszyńska, Jolanta</creator><creator>Sobkowiak, Andrzej</creator><creator>Morzycki, Jacek W.</creator><general>Elsevier Inc</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>201701</creationdate><title>Electrochemical cholesterylation of sugars with cholesteryl diphenylphosphate</title><author>Tomkiel, Aneta M. ; Siergiejczyk, Leszek ; Naróg, Dorota ; Płoszyńska, Jolanta ; Sobkowiak, Andrzej ; Morzycki, Jacek W.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c438t-38c84f4219e03dd4dd0e475318dd857c51b7cf3a67023420dfd85bd6423755383</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Cholesterol</topic><topic>Cholesterol - chemistry</topic><topic>Cholesterol - metabolism</topic><topic>Cholesteryl diphenylphosphate</topic><topic>Cholesterylation</topic><topic>Electrochemical oxidation</topic><topic>Electrochemistry - methods</topic><topic>Glycosylation</topic><topic>Molecular Structure</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tomkiel, Aneta M.</creatorcontrib><creatorcontrib>Siergiejczyk, Leszek</creatorcontrib><creatorcontrib>Naróg, Dorota</creatorcontrib><creatorcontrib>Płoszyńska, Jolanta</creatorcontrib><creatorcontrib>Sobkowiak, Andrzej</creatorcontrib><creatorcontrib>Morzycki, Jacek W.</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>Steroids</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tomkiel, Aneta M.</au><au>Siergiejczyk, Leszek</au><au>Naróg, Dorota</au><au>Płoszyńska, Jolanta</au><au>Sobkowiak, Andrzej</au><au>Morzycki, Jacek W.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Electrochemical cholesterylation of sugars with cholesteryl diphenylphosphate</atitle><jtitle>Steroids</jtitle><addtitle>Steroids</addtitle><date>2017-01</date><risdate>2017</risdate><volume>117</volume><spage>44</spage><epage>51</epage><pages>44-51</pages><issn>0039-128X</issn><eissn>1878-5867</eissn><abstract>Electrochemical reactions of sugars with cholesteryl diphenylphosphate provide different polycholesterylated products. [Display omitted]
•Electrochemical reactions of sugars with cholesteryl diphenylphosphate provide glycoconjugates.•The cholesterylation reactions are completely stereoselective.•Polyol reactions yield mono-, di-, tri-, or tetra-cholesterylated products.
Electrochemical cholesterylation of various sugars with cholesteryl diphenylphosphate was studied. The reaction afforded mono-, di-, tri-, and tetra-cholesterylated products using equivalent amounts of the reagent. The reactions turned out to be completely stereoselective with respect to both sugar and steroid but only partially regioselective – primary and anomeric hydroxyl groups in sugars were the most reactive ones while no substantial differences in reactivity was found for different secondary hydroxyl groups.</abstract><cop>United States</cop><pub>Elsevier Inc</pub><pmid>27263439</pmid><doi>10.1016/j.steroids.2016.05.011</doi><tpages>8</tpages></addata></record> |
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| issn | 0039-128X 1878-5867 |
| language | eng |
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| source | MEDLINE; ScienceDirect Journals (5 years ago - present) |
| subjects | Cholesterol Cholesterol - chemistry Cholesterol - metabolism Cholesteryl diphenylphosphate Cholesterylation Electrochemical oxidation Electrochemistry - methods Glycosylation Molecular Structure Stereoisomerism |
| title | Electrochemical cholesterylation of sugars with cholesteryl diphenylphosphate |
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