G. Pazynina, V. Nasonov, I. Belyanchikov, R. Brossmer, Maxim Maisel, A. Tuzikov, N. Bovin
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引用次数: 2
摘要
此前我们报道了一种在Koenigs-Knorr反应条件下制备α2-6低聚唾液糖的简便高效方法。使用Ag2CO3可以用乙酰化n -乙酰神经氨酸甲酯氯作为糖基供体对单糖和双糖的半乳糖-4,6-二醇进行α2-6唾液化。在本研究中，我们将该方法应用于神经氨酸的其他衍生物，即Neu5Gc、9-脱氧-9- nac - neu5ac、Neu5Acα2-8Neu5Ac和Neu5Acα2-8Neu5Ac作为糖基供体;合成了neu5ac α- o (CH2)3NH2(8)、neu5ac α- 2- 6galβ 1- 4glcnac β- o (CH2)3NH2(10)、9-脱氧-9- nac - neu5ac - o (CH2)3NH2(15)、9-脱氧-9- nac - neu5ac α- 2- 6galβ 1- 4glcnac β- o (CH2)3NH2(17)、neu5ac α- 2- 8neu5ac α- o (CH2)3NH2(23)、neu5ac α- 2- 8neu5ac α- och2 (p-C6H4)NHCOCH2NH2(25)、neu5ac α- 2- 8neu5ac α- och2 (p-C6H4)NHCOCH2NH2和neu5ac α- 2- 8neu5ac α- o (CH2)3NH2(32)。这些硅皂苷被用于siglecs和其他碳水化合物结合蛋白的表征。
Koenigs-Knorr Glycosylation with Neuraminic Acid Derivatives
Earlier we reported a convenient and efficient method of preparing α2-6 sialooligosaccharides in conditions of Koenigs-Knorr reaction. The use of Ag2CO3 allowed carrying out α2-6 sialylation of galacto-4,6-diol of mono- and disaccharides with chloride of acetylated N-acetylneuraminic acid methyl ester as glycosyl donor. In this study we applied this approach to other derivatives of neuraminic acid, namely, Neu5Gc, 9-deoxy-9-NAc-Neu5Ac, Neu5Acα2-8Neu5Ac, and Neu5Acα2-8Neu5Acα2-8Neu5Ac as glycosyl donors; eight compounds were synthesized: Neu5Gcα-O(CH2)3NH2 (8), Neu5Gcα2-6Galβ1-4GlcNAcβ-O(CH2)3NH2 (10), 9-deoxy-9-NAc-Neu5Ac-O(CH2)3NH2 (15), 9-deoxy-9-NAc-Neu5Acα2-6Galβ1-4GlcNAcβ-O(CH2)3NH2 (17), Neu5Acα2-8Neu5Acα-O(CH2)3NH2(23) Neu5Acα2-8Neu5Acα-OCH3 (24), Neu5Acα2-8Neu5Acα-OCH2(p-C6H4)NHCOCH2NH2 (25), and Neu5Acα2-8Neu5Acα2-8Neu5Acα-O(CH2)3NH2 (32). These sialosides were used for characterization of siglecs and other carbohydrate-binding proteins.
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