Substitution of the Participating Group of Glycosyl Donors by a Halogen Atom: Influence on the Rearrangement of Transient Orthoesters Formed during Glycosylation Reactions
Substitution of the participating group of glycosyl donors by a halogen atom is shown to specifically induce degradation of transient orthoesters formed during glycosylation reactions, depending on the nature of the acceptor, and to affect the protonation profile of those intermediates. Following th...
Gespeichert in:
| Veröffentlicht in: | Journal of organic chemistry 2017-03, Vol.82 (6), p.3291-3297 |
|---|---|
| Hauptverfasser: | , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 3297 |
|---|---|
| container_issue | 6 |
| container_start_page | 3291 |
| container_title | Journal of organic chemistry |
| container_volume | 82 |
| creator | Joosten, Antoine Boultadakis-Arapinis, Mélissa Gandon, Vincent Micouin, Laurent Lecourt, Thomas |
| description | Substitution of the participating group of glycosyl donors by a halogen atom is shown to specifically induce degradation of transient orthoesters formed during glycosylation reactions, depending on the nature of the acceptor, and to affect the protonation profile of those intermediates. Following these findings, bromo- and chloroacetates, which are major protecting groups in glycochemistry because they are orthogonal to other esters, should be considered with care as participating groups in the future. |
| doi_str_mv | 10.1021/acs.joc.6b03088 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_hal_p</sourceid><recordid>TN_cdi_hal_primary_oai_HAL_hal_02046285v1</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1866296459</sourcerecordid><originalsourceid>FETCH-LOGICAL-a367t-1ebf9b89934462a171988d3baeb29f3a18d904d17848e794c4481092fa925d003</originalsourceid><addsrcrecordid>eNp1kU1vGyEQhlHVqnHTnnurODaq1gH2C3qzksaOZClRmp7RLMvaRLvgAhvJv6l_smzWza1cYOCdZ4Z5EfpMyZISRi9BheWTU8uqITnh_A1a0JKRrBKkeIsWhDCW5azKz9CHEJ5IWmVZvkdnjNOasLJeoD8_xyZEE8donMWuw3Gv8T34aJQ5QDR2h9fejYfpad0flQvHHl8763zAzRED3kDvdtriVXTDd3xru37UVmmcaBPqQYP3YHd60DZOkMcUBTMFdz7unQ5RJ9SN84NucTv6l4qnQvDSVEKo6RA-oncd9EF_Ou3n6NfNj8erTba9W99erbYZ5FUdM6qbTjRciLwoKga0poLzNm9AN0x0OVDepvG0tOYF17UoVFFwSgTrQLCyJSQ_Rxczdw-9PHgzgD9KB0ZuVls53RFGEpmXzzRpv87ag3e_x_QbOZigdN-D1W4MkvKqYqIqSpGkl7NUeReC190rmxI5uSmTmzK5KU9upowvJ_jYpPG86v_ZlwTfZsGcOXqb5vJf3F-jqKyl</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1866296459</pqid></control><display><type>article</type><title>Substitution of the Participating Group of Glycosyl Donors by a Halogen Atom: Influence on the Rearrangement of Transient Orthoesters Formed during Glycosylation Reactions</title><source>American Chemical Society Journals</source><creator>Joosten, Antoine ; Boultadakis-Arapinis, Mélissa ; Gandon, Vincent ; Micouin, Laurent ; Lecourt, Thomas</creator><creatorcontrib>Joosten, Antoine ; Boultadakis-Arapinis, Mélissa ; Gandon, Vincent ; Micouin, Laurent ; Lecourt, Thomas</creatorcontrib><description>Substitution of the participating group of glycosyl donors by a halogen atom is shown to specifically induce degradation of transient orthoesters formed during glycosylation reactions, depending on the nature of the acceptor, and to affect the protonation profile of those intermediates. Following these findings, bromo- and chloroacetates, which are major protecting groups in glycochemistry because they are orthogonal to other esters, should be considered with care as participating groups in the future.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/acs.joc.6b03088</identifier><identifier>PMID: 28170257</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Chemical Sciences</subject><ispartof>Journal of organic chemistry, 2017-03, Vol.82 (6), p.3291-3297</ispartof><rights>Copyright © 2017 American Chemical Society</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a367t-1ebf9b89934462a171988d3baeb29f3a18d904d17848e794c4481092fa925d003</citedby><cites>FETCH-LOGICAL-a367t-1ebf9b89934462a171988d3baeb29f3a18d904d17848e794c4481092fa925d003</cites><orcidid>0000-0002-2532-3012 ; 0000-0003-1108-9410 ; 0000-0002-9506-2583 ; 0000-0003-1080-8591</orcidid></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.joc.6b03088$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.joc.6b03088$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>230,314,776,780,881,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/28170257$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://normandie-univ.hal.science/hal-02046285$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Joosten, Antoine</creatorcontrib><creatorcontrib>Boultadakis-Arapinis, Mélissa</creatorcontrib><creatorcontrib>Gandon, Vincent</creatorcontrib><creatorcontrib>Micouin, Laurent</creatorcontrib><creatorcontrib>Lecourt, Thomas</creatorcontrib><title>Substitution of the Participating Group of Glycosyl Donors by a Halogen Atom: Influence on the Rearrangement of Transient Orthoesters Formed during Glycosylation Reactions</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>Substitution of the participating group of glycosyl donors by a halogen atom is shown to specifically induce degradation of transient orthoesters formed during glycosylation reactions, depending on the nature of the acceptor, and to affect the protonation profile of those intermediates. Following these findings, bromo- and chloroacetates, which are major protecting groups in glycochemistry because they are orthogonal to other esters, should be considered with care as participating groups in the future.</description><subject>Chemical Sciences</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNp1kU1vGyEQhlHVqnHTnnurODaq1gH2C3qzksaOZClRmp7RLMvaRLvgAhvJv6l_smzWza1cYOCdZ4Z5EfpMyZISRi9BheWTU8uqITnh_A1a0JKRrBKkeIsWhDCW5azKz9CHEJ5IWmVZvkdnjNOasLJeoD8_xyZEE8donMWuw3Gv8T34aJQ5QDR2h9fejYfpad0flQvHHl8763zAzRED3kDvdtriVXTDd3xru37UVmmcaBPqQYP3YHd60DZOkMcUBTMFdz7unQ5RJ9SN84NucTv6l4qnQvDSVEKo6RA-oncd9EF_Ou3n6NfNj8erTba9W99erbYZ5FUdM6qbTjRciLwoKga0poLzNm9AN0x0OVDepvG0tOYF17UoVFFwSgTrQLCyJSQ_Rxczdw-9PHgzgD9KB0ZuVls53RFGEpmXzzRpv87ag3e_x_QbOZigdN-D1W4MkvKqYqIqSpGkl7NUeReC190rmxI5uSmTmzK5KU9upowvJ_jYpPG86v_ZlwTfZsGcOXqb5vJf3F-jqKyl</recordid><startdate>20170317</startdate><enddate>20170317</enddate><creator>Joosten, Antoine</creator><creator>Boultadakis-Arapinis, Mélissa</creator><creator>Gandon, Vincent</creator><creator>Micouin, Laurent</creator><creator>Lecourt, Thomas</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>1XC</scope><orcidid>https://orcid.org/0000-0002-2532-3012</orcidid><orcidid>https://orcid.org/0000-0003-1108-9410</orcidid><orcidid>https://orcid.org/0000-0002-9506-2583</orcidid><orcidid>https://orcid.org/0000-0003-1080-8591</orcidid></search><sort><creationdate>20170317</creationdate><title>Substitution of the Participating Group of Glycosyl Donors by a Halogen Atom: Influence on the Rearrangement of Transient Orthoesters Formed during Glycosylation Reactions</title><author>Joosten, Antoine ; Boultadakis-Arapinis, Mélissa ; Gandon, Vincent ; Micouin, Laurent ; Lecourt, Thomas</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a367t-1ebf9b89934462a171988d3baeb29f3a18d904d17848e794c4481092fa925d003</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Chemical Sciences</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Joosten, Antoine</creatorcontrib><creatorcontrib>Boultadakis-Arapinis, Mélissa</creatorcontrib><creatorcontrib>Gandon, Vincent</creatorcontrib><creatorcontrib>Micouin, Laurent</creatorcontrib><creatorcontrib>Lecourt, Thomas</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>Hyper Article en Ligne (HAL)</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Joosten, Antoine</au><au>Boultadakis-Arapinis, Mélissa</au><au>Gandon, Vincent</au><au>Micouin, Laurent</au><au>Lecourt, Thomas</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Substitution of the Participating Group of Glycosyl Donors by a Halogen Atom: Influence on the Rearrangement of Transient Orthoesters Formed during Glycosylation Reactions</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2017-03-17</date><risdate>2017</risdate><volume>82</volume><issue>6</issue><spage>3291</spage><epage>3297</epage><pages>3291-3297</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>Substitution of the participating group of glycosyl donors by a halogen atom is shown to specifically induce degradation of transient orthoesters formed during glycosylation reactions, depending on the nature of the acceptor, and to affect the protonation profile of those intermediates. Following these findings, bromo- and chloroacetates, which are major protecting groups in glycochemistry because they are orthogonal to other esters, should be considered with care as participating groups in the future.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>28170257</pmid><doi>10.1021/acs.joc.6b03088</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0002-2532-3012</orcidid><orcidid>https://orcid.org/0000-0003-1108-9410</orcidid><orcidid>https://orcid.org/0000-0002-9506-2583</orcidid><orcidid>https://orcid.org/0000-0003-1080-8591</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0022-3263 |
| ispartof | Journal of organic chemistry, 2017-03, Vol.82 (6), p.3291-3297 |
| issn | 0022-3263 1520-6904 |
| language | eng |
| recordid | cdi_hal_primary_oai_HAL_hal_02046285v1 |
| source | American Chemical Society Journals |
| subjects | Chemical Sciences |
| title | Substitution of the Participating Group of Glycosyl Donors by a Halogen Atom: Influence on the Rearrangement of Transient Orthoesters Formed during Glycosylation Reactions |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-03T07%3A58%3A02IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_hal_p&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Substitution%20of%20the%20Participating%20Group%20of%20Glycosyl%20Donors%20by%20a%20Halogen%20Atom:%20Influence%20on%20the%20Rearrangement%20of%20Transient%20Orthoesters%20Formed%20during%20Glycosylation%20Reactions&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Joosten,%20Antoine&rft.date=2017-03-17&rft.volume=82&rft.issue=6&rft.spage=3291&rft.epage=3297&rft.pages=3291-3297&rft.issn=0022-3263&rft.eissn=1520-6904&rft_id=info:doi/10.1021/acs.joc.6b03088&rft_dat=%3Cproquest_hal_p%3E1866296459%3C/proquest_hal_p%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1866296459&rft_id=info:pmid/28170257&rfr_iscdi=true |