Light fluorous synthesis of glucosylated glycerol teichoic acids
[Display omitted] ► Two fluorous linker systems have been developed for the assembly of teichoic acids. ► Glucosylated TAs with a terminal phosphate or hydroxyl group can be synthesized. ► Light fluorous synthesis is a powerful means to rapidly assemble teichoic acids. [Display omitted] We here desc...
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| Veröffentlicht in: | Carbohydrate research 2012-07, Vol.356, p.142-151 |
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| container_title | Carbohydrate research |
| container_volume | 356 |
| creator | Hogendorf, W.F.J. Kropec, A. Filippov, D.V. Overkleeft, H.S. Huebner, J. van der Marel, G.A. Codée, J.D.C. |
| description | [Display omitted]
► Two fluorous linker systems have been developed for the assembly of teichoic acids. ► Glucosylated TAs with a terminal phosphate or hydroxyl group can be synthesized. ► Light fluorous synthesis is a powerful means to rapidly assemble teichoic acids.
[Display omitted]
We here describe the synthesis of glucosylated teichoic acid (TA) fragments using two complementary fluorous scaffolds. The use of a perfluorooctylpropylsulfonylethyl (F-Pse) linker in combination with (glucosyl)glycerol phosphoramidite building blocks allows for the assembly of TA fragments with a terminal phosphate mono-ester, whereas the use of a perfluorooctylsuccinyl spacer delivers TA oligomers featuring a terminal alcohol functionality. These complementary linker systems have been developed because the nature of the TA chain terminus can play a role in the biological activity of the synthetic TAs. A novel α-glucosylated glycerolphosphoramidite building block is introduced to allow for a robust light fluorous synthetic protocol. |
| doi_str_mv | 10.1016/j.carres.2012.02.023 |
| format | Article |
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► Two fluorous linker systems have been developed for the assembly of teichoic acids. ► Glucosylated TAs with a terminal phosphate or hydroxyl group can be synthesized. ► Light fluorous synthesis is a powerful means to rapidly assemble teichoic acids.
[Display omitted]
We here describe the synthesis of glucosylated teichoic acid (TA) fragments using two complementary fluorous scaffolds. The use of a perfluorooctylpropylsulfonylethyl (F-Pse) linker in combination with (glucosyl)glycerol phosphoramidite building blocks allows for the assembly of TA fragments with a terminal phosphate mono-ester, whereas the use of a perfluorooctylsuccinyl spacer delivers TA oligomers featuring a terminal alcohol functionality. These complementary linker systems have been developed because the nature of the TA chain terminus can play a role in the biological activity of the synthetic TAs. A novel α-glucosylated glycerolphosphoramidite building block is introduced to allow for a robust light fluorous synthetic protocol.</description><identifier>ISSN: 0008-6215</identifier><identifier>EISSN: 1873-426X</identifier><identifier>DOI: 10.1016/j.carres.2012.02.023</identifier><identifier>PMID: 22429772</identifier><language>eng</language><publisher>Netherlands: Elsevier Ltd</publisher><subject>Cell Wall - chemistry ; Enterococcus faecalis - chemistry ; Fluorous ; Glucose ; Glycerol ; Glycosylation ; Hydrocarbons, Fluorinated - chemistry ; Molecular Structure ; Organophosphorus Compounds - chemistry ; Phosphate ; Phosphoramidite ; Teichoic acid ; Teichoic Acids - chemical synthesis</subject><ispartof>Carbohydrate research, 2012-07, Vol.356, p.142-151</ispartof><rights>2012 Elsevier Ltd</rights><rights>Copyright © 2012 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c362t-e00dee8228218c397e99522bd2a5c62a6ef2661d913d7d543b1fe708aef990873</citedby><cites>FETCH-LOGICAL-c362t-e00dee8228218c397e99522bd2a5c62a6ef2661d913d7d543b1fe708aef990873</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.carres.2012.02.023$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,777,781,3537,27905,27906,45976</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/22429772$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Hogendorf, W.F.J.</creatorcontrib><creatorcontrib>Kropec, A.</creatorcontrib><creatorcontrib>Filippov, D.V.</creatorcontrib><creatorcontrib>Overkleeft, H.S.</creatorcontrib><creatorcontrib>Huebner, J.</creatorcontrib><creatorcontrib>van der Marel, G.A.</creatorcontrib><creatorcontrib>Codée, J.D.C.</creatorcontrib><title>Light fluorous synthesis of glucosylated glycerol teichoic acids</title><title>Carbohydrate research</title><addtitle>Carbohydr Res</addtitle><description>[Display omitted]
► Two fluorous linker systems have been developed for the assembly of teichoic acids. ► Glucosylated TAs with a terminal phosphate or hydroxyl group can be synthesized. ► Light fluorous synthesis is a powerful means to rapidly assemble teichoic acids.
[Display omitted]
We here describe the synthesis of glucosylated teichoic acid (TA) fragments using two complementary fluorous scaffolds. The use of a perfluorooctylpropylsulfonylethyl (F-Pse) linker in combination with (glucosyl)glycerol phosphoramidite building blocks allows for the assembly of TA fragments with a terminal phosphate mono-ester, whereas the use of a perfluorooctylsuccinyl spacer delivers TA oligomers featuring a terminal alcohol functionality. These complementary linker systems have been developed because the nature of the TA chain terminus can play a role in the biological activity of the synthetic TAs. A novel α-glucosylated glycerolphosphoramidite building block is introduced to allow for a robust light fluorous synthetic protocol.</description><subject>Cell Wall - chemistry</subject><subject>Enterococcus faecalis - chemistry</subject><subject>Fluorous</subject><subject>Glucose</subject><subject>Glycerol</subject><subject>Glycosylation</subject><subject>Hydrocarbons, Fluorinated - chemistry</subject><subject>Molecular Structure</subject><subject>Organophosphorus Compounds - chemistry</subject><subject>Phosphate</subject><subject>Phosphoramidite</subject><subject>Teichoic acid</subject><subject>Teichoic Acids - chemical synthesis</subject><issn>0008-6215</issn><issn>1873-426X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kE9LxDAQxYMo7rr6DUR69NKaTNu0uYiy-A8WvCh4C9lkupulu9GkFfrtTdnVozAwPPjNvJlHyCWjGaOM32wyrbzHkAFlkNGx8iMyZXWVpwXwj2MypZTWKQdWTshZCJsoKa_4KZkAFCCqCqbkbmFX6y5p2t5514ckDLtujcGGxDXJqu21C0OrOjRRDBq9a5MOrV47qxOlrQnn5KRRbcCLQ5-R98eHt_lzunh9epnfL1Kdc-hSpNQg1gA1sFrnokIhSoClAVVqDopjA5wzI1huKlMW-ZI1WNFaYSMEjT_NyPV-76d3Xz2GTm5t0Ni2aofxcMkoMAaciSKixR7V3oXgsZGf3m6VHyIkx-zkRu6zk2N2ko6Vx7Grg0O_3KL5G_oNKwK3ewDjn98WvQza4k6jsR51J42z_zv8AGCKgas</recordid><startdate>20120715</startdate><enddate>20120715</enddate><creator>Hogendorf, W.F.J.</creator><creator>Kropec, A.</creator><creator>Filippov, D.V.</creator><creator>Overkleeft, H.S.</creator><creator>Huebner, J.</creator><creator>van der Marel, G.A.</creator><creator>Codée, J.D.C.</creator><general>Elsevier Ltd</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>20120715</creationdate><title>Light fluorous synthesis of glucosylated glycerol teichoic acids</title><author>Hogendorf, W.F.J. ; Kropec, A. ; Filippov, D.V. ; Overkleeft, H.S. ; Huebner, J. ; van der Marel, G.A. ; Codée, J.D.C.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c362t-e00dee8228218c397e99522bd2a5c62a6ef2661d913d7d543b1fe708aef990873</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Cell Wall - chemistry</topic><topic>Enterococcus faecalis - chemistry</topic><topic>Fluorous</topic><topic>Glucose</topic><topic>Glycerol</topic><topic>Glycosylation</topic><topic>Hydrocarbons, Fluorinated - chemistry</topic><topic>Molecular Structure</topic><topic>Organophosphorus Compounds - chemistry</topic><topic>Phosphate</topic><topic>Phosphoramidite</topic><topic>Teichoic acid</topic><topic>Teichoic Acids - chemical synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hogendorf, W.F.J.</creatorcontrib><creatorcontrib>Kropec, A.</creatorcontrib><creatorcontrib>Filippov, D.V.</creatorcontrib><creatorcontrib>Overkleeft, H.S.</creatorcontrib><creatorcontrib>Huebner, J.</creatorcontrib><creatorcontrib>van der Marel, G.A.</creatorcontrib><creatorcontrib>Codée, J.D.C.</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>Carbohydrate research</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hogendorf, W.F.J.</au><au>Kropec, A.</au><au>Filippov, D.V.</au><au>Overkleeft, H.S.</au><au>Huebner, J.</au><au>van der Marel, G.A.</au><au>Codée, J.D.C.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Light fluorous synthesis of glucosylated glycerol teichoic acids</atitle><jtitle>Carbohydrate research</jtitle><addtitle>Carbohydr Res</addtitle><date>2012-07-15</date><risdate>2012</risdate><volume>356</volume><spage>142</spage><epage>151</epage><pages>142-151</pages><issn>0008-6215</issn><eissn>1873-426X</eissn><abstract>[Display omitted]
► Two fluorous linker systems have been developed for the assembly of teichoic acids. ► Glucosylated TAs with a terminal phosphate or hydroxyl group can be synthesized. ► Light fluorous synthesis is a powerful means to rapidly assemble teichoic acids.
[Display omitted]
We here describe the synthesis of glucosylated teichoic acid (TA) fragments using two complementary fluorous scaffolds. The use of a perfluorooctylpropylsulfonylethyl (F-Pse) linker in combination with (glucosyl)glycerol phosphoramidite building blocks allows for the assembly of TA fragments with a terminal phosphate mono-ester, whereas the use of a perfluorooctylsuccinyl spacer delivers TA oligomers featuring a terminal alcohol functionality. These complementary linker systems have been developed because the nature of the TA chain terminus can play a role in the biological activity of the synthetic TAs. A novel α-glucosylated glycerolphosphoramidite building block is introduced to allow for a robust light fluorous synthetic protocol.</abstract><cop>Netherlands</cop><pub>Elsevier Ltd</pub><pmid>22429772</pmid><doi>10.1016/j.carres.2012.02.023</doi><tpages>10</tpages></addata></record> |
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| ispartof | Carbohydrate research, 2012-07, Vol.356, p.142-151 |
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| language | eng |
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| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | Cell Wall - chemistry Enterococcus faecalis - chemistry Fluorous Glucose Glycerol Glycosylation Hydrocarbons, Fluorinated - chemistry Molecular Structure Organophosphorus Compounds - chemistry Phosphate Phosphoramidite Teichoic acid Teichoic Acids - chemical synthesis |
| title | Light fluorous synthesis of glucosylated glycerol teichoic acids |
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