Stereoselective Construction of β‐Mannopyranosides by Anomeric O‐Alkylation: Synthesis of the Trisaccharide Core of N‐linked Glycans
dc.contributor.author | Nguyen, Hai | |
dc.contributor.author | Zhu, Danyang | |
dc.contributor.author | Li, Xiaohua | |
dc.contributor.author | Zhu, Jianglong | |
dc.date.accessioned | 2017-06-16T20:16:38Z | |
dc.date.available | 2017-06-16T20:16:38Z | |
dc.date.issued | 2016-04-04 | |
dc.identifier.citation | Nguyen, Hai; Zhu, Danyang; Li, Xiaohua; Zhu, Jianglong (2016). "Stereoselective Construction of β‐Mannopyranosides by Anomeric O‐Alkylation: Synthesis of the Trisaccharide Core of N‐linked Glycans." Angewandte Chemie 128(15): 4845-4849. | |
dc.identifier.issn | 0044-8249 | |
dc.identifier.issn | 1521-3757 | |
dc.identifier.uri | https://hdl.handle.net/2027.42/137600 | |
dc.description.abstract | A new and efficient approach for direct and stereoselective synthesis of β‐mannopyranosides by anomeric O‐alkylation has been developed. This anomeric O‐alkylation of mannopyranose‐derived lactols is proposed to occur under synergistic control of a kinetic anomeric effect and metal chelation. The presence of a conformationally flexible C6 oxygen atom in the sugar‐derived lactol donors is required for this anomeric O‐alkylation to be efficient, probably because of its chelation with cesium ion. In contrast, the presence of a C2 oxygen atom plays a minor role. This glycosylation method has been successfully utilized for the synthesis of the trisaccharide core of complex N‐linked glycans.Lactol‐Kontrolle: Die Titelreaktion könnte synergistisch durch einen kinetischen anomeren Effekt und Metallchelatisierung gesteuert ablaufen. Nur mit einem an der C6‐Position des Lactols befindlichen, konformativ flexiblen Sauerstoffatom, das vermutlich chelatisierend an ein Caesiumion bindet, ist die Reaktion effizient. Diese Glykosylierungsmethode bewährte sich in der Synthese der Trisaccharid‐Kerns komplexer N‐verknüpfter Glykane. | |
dc.publisher | Oxford University Press | |
dc.publisher | Wiley Periodicals, Inc. | |
dc.subject.other | β-Mannosylierungen | |
dc.subject.other | Oligosaccharide | |
dc.subject.other | N-verknüpfte Glykane | |
dc.subject.other | Glykosylierungen | |
dc.subject.other | Anomere O-Alkylierung | |
dc.title | Stereoselective Construction of β‐Mannopyranosides by Anomeric O‐Alkylation: Synthesis of the Trisaccharide Core of N‐linked Glycans | |
dc.type | Article | en_US |
dc.rights.robots | IndexNoFollow | |
dc.subject.hlbsecondlevel | Chemical Engineering | |
dc.subject.hlbsecondlevel | Chemistry | |
dc.subject.hlbsecondlevel | Materials Science and Engineering | |
dc.subject.hlbtoplevel | Engineering | |
dc.subject.hlbtoplevel | Science | |
dc.description.peerreviewed | Peer Reviewed | |
dc.description.bitstreamurl | https://deepblue.lib.umich.edu/bitstream/2027.42/137600/1/ange201600488_am.pdf | |
dc.description.bitstreamurl | https://deepblue.lib.umich.edu/bitstream/2027.42/137600/2/ange201600488-sup-0001-misc_information.pdf | |
dc.description.bitstreamurl | https://deepblue.lib.umich.edu/bitstream/2027.42/137600/3/ange201600488.pdf | |
dc.identifier.doi | 10.1002/ange.201600488 | |
dc.identifier.source | Angewandte Chemie | |
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dc.owningcollname | Interdisciplinary and Peer-Reviewed |
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