Branching of poly(ADP-ribose): Synthesis of the Core Motif
The synthesis of the core motif of branched poly(adenosine diphosphate ribose) (poly(ADPr)) is described, and structural analysis reasserted the proposed stereochemistry for branching. For the synthesis, a ribose trisaccharide was first constructed with only α-O-glycosidic linkages. Finally, the a...
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| Veröffentlicht in: | Organic letters 2015-09, Vol.17 (17), p.4328-4331 |
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| container_title | Organic letters |
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| creator | Kistemaker, Hans A. V Overkleeft, Herman S van der Marel, Gijsbert A Filippov, Dmitri V |
| description | The synthesis of the core motif of branched poly(adenosine diphosphate ribose) (poly(ADPr)) is described, and structural analysis reasserted the proposed stereochemistry for branching. For the synthesis, a ribose trisaccharide was first constructed with only α-O-glycosidic linkages. Finally, the adenine nucleobase was introduced via a Vorbrüggen-type glycosylation reaction. The orthogonality of the selected protecting groups was demonstrated, allowing for the construction of branched poly(ADPr) oligomers in the near future. |
| doi_str_mv | 10.1021/acs.orglett.5b02143 |
| format | Article |
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The orthogonality of the selected protecting groups was demonstrated, allowing for the construction of branched poly(ADPr) oligomers in the near future.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/acs.orglett.5b02143</identifier><identifier>PMID: 26307949</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Glycosylation ; Molecular Structure ; Nuclear Magnetic Resonance, Biomolecular ; Poly Adenosine Diphosphate Ribose - chemical synthesis ; Poly Adenosine Diphosphate Ribose - chemistry</subject><ispartof>Organic letters, 2015-09, Vol.17 (17), p.4328-4331</ispartof><rights>Copyright © 2015 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a411t-92501776b80e4194bb022b7627e209c71f986d75a796627dcedac87f20f33ed13</citedby><cites>FETCH-LOGICAL-a411t-92501776b80e4194bb022b7627e209c71f986d75a796627dcedac87f20f33ed13</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.5b02143$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.orglett.5b02143$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26307949$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kistemaker, Hans A. 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The orthogonality of the selected protecting groups was demonstrated, allowing for the construction of branched poly(ADPr) oligomers in the near future.</description><subject>Glycosylation</subject><subject>Molecular Structure</subject><subject>Nuclear Magnetic Resonance, Biomolecular</subject><subject>Poly Adenosine Diphosphate Ribose - chemical synthesis</subject><subject>Poly Adenosine Diphosphate Ribose - chemistry</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kM1OwzAQhC0EoqXwBEgox3JI67UTO-6tlF-pCCTgbDmJ3aZK42Inh749rho4ctrVeGbX-yF0DXgCmMBUFX5i3arWbTtJ86Ak9AQNISU05jglp389wwN04f0GYwiKOEcDwijmIhFDNLtzqinWVbOKrIl2tt6P5_fvsaty6_XtLPrYN-1a-8ofnkMXLazT0attK3OJzoyqvb7q6wh9PT58Lp7j5dvTy2K-jFUC0MaCpBg4Z3mGdQIiycNXSc4Z4ZpgUXAwImMlTxUXLIhloUtVZNwQbCjVJdARGh_n7pz97rRv5bbyha5r1WjbeQkcCw6QMRas9GgtnPXeaSN3rtoqt5eA5QGaDNBkD0320ELqpl_Q5Vtd_mV-KQXD9Gg4pDe2c02499-RPw2yeKA</recordid><startdate>20150904</startdate><enddate>20150904</enddate><creator>Kistemaker, Hans A. 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V ; Overkleeft, Herman S ; van der Marel, Gijsbert A ; Filippov, Dmitri V</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a411t-92501776b80e4194bb022b7627e209c71f986d75a796627dcedac87f20f33ed13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Glycosylation</topic><topic>Molecular Structure</topic><topic>Nuclear Magnetic Resonance, Biomolecular</topic><topic>Poly Adenosine Diphosphate Ribose - chemical synthesis</topic><topic>Poly Adenosine Diphosphate Ribose - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kistemaker, Hans A. V</creatorcontrib><creatorcontrib>Overkleeft, Herman S</creatorcontrib><creatorcontrib>van der Marel, Gijsbert A</creatorcontrib><creatorcontrib>Filippov, Dmitri V</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>Kistemaker, Hans A. V</au><au>Overkleeft, Herman S</au><au>van der Marel, Gijsbert A</au><au>Filippov, Dmitri V</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Branching of poly(ADP-ribose): Synthesis of the Core Motif</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2015-09-04</date><risdate>2015</risdate><volume>17</volume><issue>17</issue><spage>4328</spage><epage>4331</epage><pages>4328-4331</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>The synthesis of the core motif of branched poly(adenosine diphosphate ribose) (poly(ADPr)) is described, and structural analysis reasserted the proposed stereochemistry for branching. For the synthesis, a ribose trisaccharide was first constructed with only α-O-glycosidic linkages. Finally, the adenine nucleobase was introduced via a Vorbrüggen-type glycosylation reaction. The orthogonality of the selected protecting groups was demonstrated, allowing for the construction of branched poly(ADPr) oligomers in the near future.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>26307949</pmid><doi>10.1021/acs.orglett.5b02143</doi><tpages>4</tpages></addata></record> |
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| source | ACS Publications; MEDLINE |
| subjects | Glycosylation Molecular Structure Nuclear Magnetic Resonance, Biomolecular Poly Adenosine Diphosphate Ribose - chemical synthesis Poly Adenosine Diphosphate Ribose - chemistry |
| title | Branching of poly(ADP-ribose): Synthesis of the Core Motif |
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