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Sialic Acid Linkage Specific Derivatization of Glycosphingolipid Glycans by Ring-Opening Aminolysis of Lactones
Analytical Chemistry ( IF 6.7 ) Pub Date : 2018-10-17 00:00:00 , DOI: 10.1021/acs.analchem.8b02775 Hisatoshi Hanamatsu 1, 2 , Takashi Nishikaze 3 , Nobuaki Miura 4 , Jinhua Piao 2 , Kazue Okada 2 , Sadanori Sekiya 3 , Shinichi Iwamoto 3 , Naoya Sakamoto 1 , Koichi Tanaka 3 , Jun-ichi Furukawa 2
Analytical Chemistry ( IF 6.7 ) Pub Date : 2018-10-17 00:00:00 , DOI: 10.1021/acs.analchem.8b02775 Hisatoshi Hanamatsu 1, 2 , Takashi Nishikaze 3 , Nobuaki Miura 4 , Jinhua Piao 2 , Kazue Okada 2 , Sadanori Sekiya 3 , Shinichi Iwamoto 3 , Naoya Sakamoto 1 , Koichi Tanaka 3 , Jun-ichi Furukawa 2
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Sialic acids occur widely as glycoconjugates at the nonreducing ends of glycans. Glycosphingolipids (GSLs) include a large number of sialyl-linked glycan isomers with α2,3-, α2,6-, and α2,8-linked polysialic acids. Thus, it is difficult to distinguish structural isomers with the same mass by mass spectrometry. The sialic acid linkage specific alkylamidation (SALSA) method has been developed for discriminating between α2,3- and α2,6-linked isomers, but sequential amidation of linkage-specific sialic acids is generally complicated and time-consuming. Moreover, analysis of GSL-glycans containing α2,8-linked polysialic acids using solid-phase SALSA has not been reported. Herein, we report a novel SALSA method focused on ring-opening aminolysis (aminolysis-SALSA), which shortens the reaction time and simplifies the experimental procedures. We demonstrate that aminolysis-SALSA can successfully distinguish serum GSL-glycan isomers by mass spectrometry. In addition, ring-opening aminolysis can easily be applied to amine and hydrazine derivatives.
中文翻译：
内酯的内酯开环水解对糖鞘脂聚糖的唾液酸键的特异性衍生作用
唾液酸作为糖缀合物广泛存在于聚糖的非还原端。糖鞘脂（GSL）包括大量的与α2,3-，α2,6-和α2,8连接的多唾液酸的唾液酸连接的聚糖异构体。因此，通过质谱法难以区分具有相同质量的结构异构体。已经开发了唾液酸键合特异性烷基酰胺化（SALSA）方法来区分α2，3-和α2，6-连接的异构体，但是键合特异性唾液酸的顺序酰胺化通常是复杂且耗时的。此外，尚未报道使用固相SALSA分析含有α2，8-连接的多唾液酸的GSL-聚糖。在本文中，我们报告了一种新型的SALSA方法，该方法侧重于开环氨解（aminolysis-SALSA），它缩短了反应时间并简化了实验程序。我们证明，氨解-SALSA可以通过质谱成功地区分血清GSL-聚糖异构体。另外，开环氨解可容易地应用于胺和肼衍生物。
更新日期：2018-10-17
中文翻译：
内酯的内酯开环水解对糖鞘脂聚糖的唾液酸键的特异性衍生作用
唾液酸作为糖缀合物广泛存在于聚糖的非还原端。糖鞘脂（GSL）包括大量的与α2,3-，α2,6-和α2,8连接的多唾液酸的唾液酸连接的聚糖异构体。因此，通过质谱法难以区分具有相同质量的结构异构体。已经开发了唾液酸键合特异性烷基酰胺化（SALSA）方法来区分α2，3-和α2，6-连接的异构体，但是键合特异性唾液酸的顺序酰胺化通常是复杂且耗时的。此外，尚未报道使用固相SALSA分析含有α2，8-连接的多唾液酸的GSL-聚糖。在本文中，我们报告了一种新型的SALSA方法，该方法侧重于开环氨解（aminolysis-SALSA），它缩短了反应时间并简化了实验程序。我们证明，氨解-SALSA可以通过质谱成功地区分血清GSL-聚糖异构体。另外，开环氨解可容易地应用于胺和肼衍生物。
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