Fragmentation behavior of glycated peptides derived from D-glucose, D-fructose and D-ribose in tandem mass spectrometry
Fragmentation behavior of glycated peptides derived from D-glucose, D-fructose and D-ribose in tandem mass spectrometry
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DOI：
10.1002/jms.1117
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发表时间：
2006-11-01
影响因子：
2.3
通讯作者：
Hoffmann, Ralf
中科院分区：
文献类型：
--
作者：
Frolov, Andrej;Hoffmann, Peter;Hoffmann, Ralf
非酶糖基化（或糖基化）是一种常见的非酶侧链特异性序列独立的翻译后修饰，由还原性碳水化合物与游离氨基反应形成。因此，蛋白质可以与醛糖或酮糖反应，分别产生阿马多里或海因斯化合物。在此，通过电喷雾 (ESI) 或基质辅助激光解吸/电离 (MALDI) 质谱 (MS) 后的碰撞诱导裂解 (CID) 研究了 D-葡萄糖和 D-核糖衍生的 Amadori 肽以及 D-果糖衍生的 Heynes 肽的裂解行为。所有三个糖部分都显示出伴随母体离子和碎片离子的特征断裂模式，这可以通过水和甲醛的连续损失来解释。葡萄糖衍生的 Amadori 母离子和碎片离子在特征强度分布下显示出 18、36、54、72 和 84 u 的损失，而 D-果糖衍生离子的损失为 18、36、54、72、84 和 96 U，核糖衍生离子的损失为 18、36 和 54 u。此外，每个糖部分都产生了指示性的赖氨酸衍生的亚胺离子，这些亚胺离子成功地用于前体离子扫描分析，以鉴定用 D-葡萄糖糖化的牛血清白蛋白 (BSA) 的胰蛋白酶消化物中的 Amadori pepticles。 BSA 在第 36、160、235、256、401 和 548 位的赖氨酸残基上进行了修饰。版权所有 (c) 2006 John Wiley & Sons, Ltd.。
Nonenzymatic glycosylation (or glycation) is a common nonenzymatic side-chain specific sequence-independent posttranslational modification formed by the reaction of reducing carbohydrates with free amino groups. Thus, proteins can react with aldoses or ketoses to yield Amadori or Heynes compounds, respectively. Here, the fragmentation behavior of D-glucose and D-ribose-derived Amadori peptides as well as D-fructose-derived Heynes peptides were studied by collision-induced fragmentation (CID) after electrospray (ESI) or matrix-assisted laser desorption/ionization (MALDI) mass spectrometry (MS). All three sugar moieties displayed characteristic fragmentation patterns accompanying the parent and the fragment ions, which could be explained by consecutive losses of water and formaldehyde. Glucose-derived Amadori parent and fragment ions displayed losses of 18, 36, 54, 72, and 84 u at a characteristic intensity distribution compared with losses of 18, 36, 54, 72, 84, and 96 U for D-fructose-derived ions and losses of 18, 36, and 54 u for ribose-derived ions. Furthermore, each sugar moiety produced indicative lysine-derived immonium ions that were successfully used in a precursor ion scan analysis to identify Amadori pepticles in a tryptic digest of bovine serum albumin (BSA) glycated with D-glucose. BSA was modified on lysine residues at positions 36, 160, 235, 256, 401, and 548. Copyright (c) 2006 John Wiley & Sons, Ltd.