Key Laboratory of Analytical Chemistry for Biology and Medicine (Ministry of Education), Department of Chemistry, Wuhan University, Wuhan, China.
Adv Exp Med Biol. 2021;1280:161-172. doi: 10.1007/978-3-030-51652-9_11.
Gain-of-function mutations of isocitrate dehydrogenase 1 and 2 (IDH1/2) were demonstrated to induce the production and accumulation of oncometabolite 2-hydroxyglutarate (2HG). 2HG is a potent competitor of α-ketoglutarate (α-KG) and can inhibit multiple α-KG-dependent dioxygenases that are critical for regulating the metabolic and epigenetic state of cells. The accumulation of 2HG contributes to elevated risk of malignant tumors. 2HG carries an asymmetric carbon atom in its carbon backbone and therefore occurs in two enantiomers, D-2-hydroxyglutarate (D-2HG) and L-2-hydroxyglutarate (L-2HG). Each enantiomer is produced and metabolized in independent biochemical pathway and catalyzed by different enzymes. The accurate diagnosis of 2HG-related diseases relies on determining the configuration of the two enantiomers. Quantitative methods for analysis of D-2HG and L-2HG have been well developed. These analytical strategies mainly include the use of chiral chromatography medium to facilitate chromatographic separation of enantiomers prior to spectroscopy or mass spectrometry analysis and the use of chiral derivatization reagents to convert the enantiomers to diastereomers with differential physical and chemical properties that can improve their chromatographic separation. Here, we summarize and discuss these established methods for analysis of total 2HG as well as the determination of the enantiomers of D-2HG and L-2HG.
IDH1/2 基因突变会导致 2-羟戊二酸(2HG)的产生和积累。2HG 是一种有效的 α-酮戊二酸(α-KG)竞争物,能够抑制多种对细胞代谢和表观遗传状态至关重要的α-KG 依赖性双加氧酶。2HG 的积累会增加恶性肿瘤的风险。2HG 在其碳骨架中有一个不对称碳原子,因此存在两种对映异构体,D-2-羟戊二酸(D-2HG)和 L-2-羟戊二酸(L-2HG)。每个对映异构体都是通过独立的生化途径产生和代谢的,由不同的酶催化。2HG 相关疾病的准确诊断依赖于确定两种对映异构体的构型。D-2HG 和 L-2HG 的定量分析方法已经得到很好的发展。这些分析策略主要包括使用手性色谱介质在光谱或质谱分析之前促进对映异构体的色谱分离,以及使用手性衍生化试剂将对映异构体转化为具有不同物理和化学性质的非对映异构体,从而改善它们的色谱分离。在这里,我们总结和讨论了这些用于分析总 2HG 以及确定 D-2HG 和 L-2HG 对映异构体的既定方法。