The first synthesis of Neu5Acα2-3Galβ1-4GlcNAcβ1-2Manα1-Ser -: a newly discovered component of α-dystroglycan

The first synthesis of Neu5Acα2-3Galβ1-4GlcNAcβ1-2Manα1-Ser -: a newly discovered component of α-dystroglycan
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DOI:
10.1016/s0040-4039(99)00930-2
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发表时间:
1999-07-02
影响因子:
1.8
通讯作者:
Ajisaka, K
Ajisaka, K
中科院分区:
化学4区
文献类型:
--
作者:
Matsuo, I;Isomura, M;Ajisaka, K

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糖肽(1),Neu 5 β 2 -3Gal β 1-4GlcNAc β 1- 2 Man α 1-Ser,采用化学酶法合成。使用糖苷酶辅助的低聚糖合成制备Gal beta 1-4GlcNA beta 1- 2 Man三糖。在通过化学糖基化将该三糖与丝氨酸衍生物偶联后,使用唾液酸转移酶引入唾液酸以产生四糖丝氨酸衍生物。除去保护基得到糖肽(1)。使用化学酶策略允许消除许多合成步骤和有效制备目标化合物。(C)1999爱思唯尔科技有限公司。保留所有权利。
Glycopeptide (1), Neu5Aca2-3Gal beta 1-4GlcNAc beta 1-2Man alpha 1-Ser, was synthesized using a chemoenzymatic strategy. Gal beta 1-4GlcNA beta 1-2Man trisaccharide was prepared using glycosidase assisted oligosaccharide synthesis. After coupling of this trisaccharide with a serine derivative by chemical glycosylation, sialic add was introduced using sialyltransferase to produce a tetrasaccharide serine derivative. Removal of protecting group afforded glycopeptide (1). Use of a chemoenzymatic strategy allowed for the elimination of numerous synthetic steps and efficient preparation of the target compound. (C) 1999 Elsevier Science Ltd. All rights reserved.