Full metadata record
DC Field | Value | Language |
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dc.contributor.author | Asressu, Kesatebrhan Haile | en_US |
dc.contributor.author | Wang, Cheng-Chung | en_US |
dc.date.accessioned | 2018-08-21T05:52:57Z | - |
dc.date.available | 2018-08-21T05:52:57Z | - |
dc.date.issued | 2017-12-14 | en_US |
dc.identifier.issn | 0008-6215 | en_US |
dc.identifier.uri | http://dx.doi.org/10.1016/j.carres.2017.10.007 | en_US |
dc.identifier.uri | http://hdl.handle.net/11536/144124 | - |
dc.description.abstract | In N-acetylneuraminic acid, apart from O9 and O8, a possible glycosylation site is the O4 position. For example, gangliosides HLG-2 and HPG-7 are considered to be potential lead compounds for carbohydrate-based drug development to treat neural disorders. However, the construction of their alpha(1 -> 4) fucosyl sialic acid and alpha(2 -> 4) linkages between sialic acids is difficult because of the regioselectivity problem. Herein, N-acetyl-2,7-anhydroneuraminic acid was synthesized in three steps from Neu5Ac methyl ester through per-O-trimethylsilylation, heating-assisted intramolecular anomeric protection (iMAP) and desilylation. The iMAP simultaneously circumvents both the 2- and 7-OH protection. Upon protecting the 8- and 9-OH groups as a benzylidene acetal, only 4-OH is free for glycosylation. These 2,7-anhydro-8,9-O-benzylidenesialic acid derivatives were examined as acceptor for an alpha-selective fucosylation to construct the glycosidic linkage of fucosyl alpha(1 -> 4) 2,7-anhydroneuraminic acid. (C) 2017 Published by Elsevier Ltd. | en_US |
dc.language.iso | en_US | en_US |
dc.subject | N-Acetyl-2,7-anhydroneuraminic acid | en_US |
dc.subject | Fucosyl alpha(1 -> 4) sialic acid linkage | en_US |
dc.subject | Ganglioside HPG-7 | en_US |
dc.title | Concise synthesis of 2,7-anhydrosialic acid derivatives and its application | en_US |
dc.type | Article | en_US |
dc.identifier.doi | 10.1016/j.carres.2017.10.007 | en_US |
dc.identifier.journal | CARBOHYDRATE RESEARCH | en_US |
dc.citation.volume | 453-454 | en_US |
dc.citation.spage | 44 | en_US |
dc.citation.epage | 53 | en_US |
dc.contributor.department | 應用化學系 | zh_TW |
dc.contributor.department | Department of Applied Chemistry | en_US |
dc.identifier.wosnumber | WOS:000416212600006 | en_US |
Appears in Collections: | Articles |