Synthesis of a glycopeptide containing oligosaccharides: Chemoenzymatic synthesis of eel calcitonin analogues having natural N-linked oligosaccharides
Synthesis of a glycopeptide containing oligosaccharides: Chemoenzymatic synthesis of eel calcitonin analogues having natural N-linked oligosaccharides
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DOI：
10.1021/ja9831305
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发表时间：
1999-01-20
影响因子：
15
通讯作者：
Inazu, T
中科院分区：
文献类型：
--
作者：
Mizuno, M;Haneda, K;Inazu, T
我们描述了具有天然N-连接寡糖的鳗鱼降钙素（eCT）糖肽类似物的新型化学酶促合成，例如作为糖蛋白合成的模型化合物的二唾液酸双触角复合物I型（NeuAc-Gal-GlcNAc-Man）（2）-Man-GlcNAc（2）]、去唾液酸复合物型[（Gal-GlcNAc-Man）（2）-Man-GlcNAc（2）]和高甘露糖型[MansGlcNAc（2）]。首先，通过化学合成制备含有N-乙酰葡糖胺（GlcNAc）的糖蛋白。接着，通过使用来自冬季毛霉的内切-β-N-乙酰氨基葡糖苷酶（内切-β-GlcNAc-酶）的转糖基化反应，将天然寡糖添加到制备的含有GlcNAc的糖肽中。
We describe a novel chemoenzymatic synthesis of eel calcitonin (eCT) glycopeptide analogues having natural N-linked oligosaccharides, such as a disialo biantennary complex-type I(NeuAc-Gal-GlcNAc-Man)(2)-Man-GlcNAc(2)], an asialo complex-type [(Gal-GlcNAc-Man)(2)-Man-GlcNAc(2)], and a high-mannose type [MansGlcNAc(2)] as model compounds for glycoprotein synthesis. First, a glycoprotein containing N-acetylglucosamine (GlcNAc) was prepared by a chemical synthesis. Next, natural oligosaccharides were added to the prepared glycopeptide containing GlcNAc by a transglycosylation reaction using endo-beta-N-acetylglucosaminidase (endo-beta-GlcNAc-ase) from Mucor hiemalis.