Synthesis of α‑C-Galactosylceramide via Diastereoselective Aziridination: The New Immunostimulant 4′-epi-C-Glycoside of KRN7000
A new immunostimulant, the 4′-epimer of α-C-GalCer, was synthesized from a C 2-symmetric dienediol and α-C-allyl galactoside. The intramolecular aziridination and the following reductive ring opening provided the core of the aliphatic amino alcohol with excellent regio- and stereocontrol. The new im...
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| Veröffentlicht in: | Organic letters 2016-02, Vol.18 (4), p.808-811 |
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| creator | Chang, Ya-Jen Hsuan, Yi-Chen Lai, Alan Chuan-Ying Han, Yun-Chiann Hou, Duen-Ren |
| description | A new immunostimulant, the 4′-epimer of α-C-GalCer, was synthesized from a C 2-symmetric dienediol and α-C-allyl galactoside. The intramolecular aziridination and the following reductive ring opening provided the core of the aliphatic amino alcohol with excellent regio- and stereocontrol. The new immunostimulants 3d and 3e gave a better polarized Th1-type cytokine response in murine NKT cells than the benchmarked α-C-GalCer. |
| doi_str_mv | 10.1021/acs.orglett.6b00090 |
| format | Article |
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The intramolecular aziridination and the following reductive ring opening provided the core of the aliphatic amino alcohol with excellent regio- and stereocontrol. The new immunostimulants 3d and 3e gave a better polarized Th1-type cytokine response in murine NKT cells than the benchmarked α-C-GalCer.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/acs.orglett.6b00090</identifier><identifier>PMID: 26844691</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Adjuvants, Immunologic - chemical synthesis ; Adjuvants, Immunologic - chemistry ; Adjuvants, Immunologic - pharmacology ; Animals ; Aziridines - chemistry ; Cardiac Glycosides ; Cytokines ; Galactosylceramides - chemical synthesis ; Galactosylceramides - chemistry ; Galactosylceramides - pharmacology ; Glycosides ; Marine Biology ; Mice ; Mice, Inbred BALB C ; Molecular Structure ; Monosaccharides - chemistry ; Natural Killer T-Cells ; Porifera - chemistry ; Stereoisomerism</subject><ispartof>Organic letters, 2016-02, Vol.18 (4), p.808-811</ispartof><rights>Copyright © 2016 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a345t-999830c878f476db8012aa76423895eb22e5ff67f7135f4e9dd06d8f980c17c43</citedby><cites>FETCH-LOGICAL-a345t-999830c878f476db8012aa76423895eb22e5ff67f7135f4e9dd06d8f980c17c43</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.orglett.6b00090$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.orglett.6b00090$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>315,782,786,2767,27083,27931,27932,56745,56795</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26844691$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Chang, Ya-Jen</creatorcontrib><creatorcontrib>Hsuan, Yi-Chen</creatorcontrib><creatorcontrib>Lai, Alan Chuan-Ying</creatorcontrib><creatorcontrib>Han, Yun-Chiann</creatorcontrib><creatorcontrib>Hou, Duen-Ren</creatorcontrib><title>Synthesis of α‑C-Galactosylceramide via Diastereoselective Aziridination: The New Immunostimulant 4′-epi-C-Glycoside of KRN7000</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>A new immunostimulant, the 4′-epimer of α-C-GalCer, was synthesized from a C 2-symmetric dienediol and α-C-allyl galactoside. The intramolecular aziridination and the following reductive ring opening provided the core of the aliphatic amino alcohol with excellent regio- and stereocontrol. The new immunostimulants 3d and 3e gave a better polarized Th1-type cytokine response in murine NKT cells than the benchmarked α-C-GalCer.</description><subject>Adjuvants, Immunologic - chemical synthesis</subject><subject>Adjuvants, Immunologic - chemistry</subject><subject>Adjuvants, Immunologic - pharmacology</subject><subject>Animals</subject><subject>Aziridines - chemistry</subject><subject>Cardiac Glycosides</subject><subject>Cytokines</subject><subject>Galactosylceramides - chemical synthesis</subject><subject>Galactosylceramides - chemistry</subject><subject>Galactosylceramides - pharmacology</subject><subject>Glycosides</subject><subject>Marine Biology</subject><subject>Mice</subject><subject>Mice, Inbred BALB C</subject><subject>Molecular Structure</subject><subject>Monosaccharides - chemistry</subject><subject>Natural Killer T-Cells</subject><subject>Porifera - chemistry</subject><subject>Stereoisomerism</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kMFu1DAQhi1UREvhCSpVPnLJdpw4dtxbtS2loioSlHPkdcatqyRebKdoOfXAC_Ao8CA8RJ8Er3bpsacZjf7_n5mPkAMGMwYlO9Imzny46TGlmVgAgIIXZI_VZVVIqMudp17ALnkd4x0AyxP1iuyWouFcKLZHfn5ZjekWo4vUW_r39-PDr3lxrnttko-r3mDQg-uQ3jtNT52OCQP6iD2a5O6RnvxwwXVu1Mn58Zhe3yK9wu_0Yhim0cfkhqnXY6L88eFPgUtX5Ox-ZXxcR-Z9Hz9fyXz4G_LS6j7i223dJ1_fn13PPxSXn84v5ieXha54nQqlVFOBaWRjuRTdogFWai0FL6tG1bgoS6ytFdJKVtWWo-o6EF1jVQOGScOrffJuk7sM_tuEMbWDiwb7fCP6KbZMCgmSg6qytNpITfAxBrTtMrhBh1XLoF3jbzP-dou_3eLPrsPtgmkxYPfk-c87C442grX7zk9hzP8-G_kP-QKXDA</recordid><startdate>20160219</startdate><enddate>20160219</enddate><creator>Chang, Ya-Jen</creator><creator>Hsuan, Yi-Chen</creator><creator>Lai, Alan Chuan-Ying</creator><creator>Han, Yun-Chiann</creator><creator>Hou, Duen-Ren</creator><general>American Chemical Society</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>20160219</creationdate><title>Synthesis of α‑C-Galactosylceramide via Diastereoselective Aziridination: The New Immunostimulant 4′-epi-C-Glycoside of KRN7000</title><author>Chang, Ya-Jen ; Hsuan, Yi-Chen ; Lai, Alan Chuan-Ying ; Han, Yun-Chiann ; Hou, Duen-Ren</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a345t-999830c878f476db8012aa76423895eb22e5ff67f7135f4e9dd06d8f980c17c43</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Adjuvants, Immunologic - chemical synthesis</topic><topic>Adjuvants, Immunologic - chemistry</topic><topic>Adjuvants, Immunologic - pharmacology</topic><topic>Animals</topic><topic>Aziridines - chemistry</topic><topic>Cardiac Glycosides</topic><topic>Cytokines</topic><topic>Galactosylceramides - chemical synthesis</topic><topic>Galactosylceramides - chemistry</topic><topic>Galactosylceramides - pharmacology</topic><topic>Glycosides</topic><topic>Marine Biology</topic><topic>Mice</topic><topic>Mice, Inbred BALB C</topic><topic>Molecular Structure</topic><topic>Monosaccharides - chemistry</topic><topic>Natural Killer T-Cells</topic><topic>Porifera - chemistry</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Chang, Ya-Jen</creatorcontrib><creatorcontrib>Hsuan, Yi-Chen</creatorcontrib><creatorcontrib>Lai, Alan Chuan-Ying</creatorcontrib><creatorcontrib>Han, Yun-Chiann</creatorcontrib><creatorcontrib>Hou, Duen-Ren</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>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Chang, Ya-Jen</au><au>Hsuan, Yi-Chen</au><au>Lai, Alan Chuan-Ying</au><au>Han, Yun-Chiann</au><au>Hou, Duen-Ren</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of α‑C-Galactosylceramide via Diastereoselective Aziridination: The New Immunostimulant 4′-epi-C-Glycoside of KRN7000</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2016-02-19</date><risdate>2016</risdate><volume>18</volume><issue>4</issue><spage>808</spage><epage>811</epage><pages>808-811</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>A new immunostimulant, the 4′-epimer of α-C-GalCer, was synthesized from a C 2-symmetric dienediol and α-C-allyl galactoside. The intramolecular aziridination and the following reductive ring opening provided the core of the aliphatic amino alcohol with excellent regio- and stereocontrol. The new immunostimulants 3d and 3e gave a better polarized Th1-type cytokine response in murine NKT cells than the benchmarked α-C-GalCer.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>26844691</pmid><doi>10.1021/acs.orglett.6b00090</doi><tpages>4</tpages></addata></record> |
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| identifier | ISSN: 1523-7060 |
| ispartof | Organic letters, 2016-02, Vol.18 (4), p.808-811 |
| issn | 1523-7060 1523-7052 |
| language | eng |
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| source | American Chemical Society; MEDLINE |
| subjects | Adjuvants, Immunologic - chemical synthesis Adjuvants, Immunologic - chemistry Adjuvants, Immunologic - pharmacology Animals Aziridines - chemistry Cardiac Glycosides Cytokines Galactosylceramides - chemical synthesis Galactosylceramides - chemistry Galactosylceramides - pharmacology Glycosides Marine Biology Mice Mice, Inbred BALB C Molecular Structure Monosaccharides - chemistry Natural Killer T-Cells Porifera - chemistry Stereoisomerism |
| title | Synthesis of α‑C-Galactosylceramide via Diastereoselective Aziridination: The New Immunostimulant 4′-epi-C-Glycoside of KRN7000 |
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