標題: Concise synthesis of 2,7-anhydrosialic acid derivatives and its application
作者: Asressu, Kesatebrhan Haile
Wang, Cheng-Chung
應用化學系
Department of Applied Chemistry
關鍵字: N-Acetyl-2,7-anhydroneuraminic acid;Fucosyl alpha(1 -> 4) sialic acid linkage;Ganglioside HPG-7
公開日期: 14-十二月-2017
摘要: 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.
URI: http://dx.doi.org/10.1016/j.carres.2017.10.007
http://hdl.handle.net/11536/144124
ISSN: 0008-6215
DOI: 10.1016/j.carres.2017.10.007
期刊: CARBOHYDRATE RESEARCH
Volume: 453-454
起始頁: 44
結束頁: 53
顯示於類別:期刊論文