化学生物学解析疾病中O-GlcNAc糖基化功能: 研究工具与策略

doi:10.6023/A23020040

摘要/Abstract

O-连接β-N-乙酰葡糖胺(O-GlcNAc)糖基化是广泛存在于蛋白质丝/苏氨酸残基的翻译后修饰. 这一动态、可逆单糖修饰以位点特异性方式影响底物蛋白的结构和生物学功能, 参与调控几乎所有细胞生理过程和重大疾病的演进过程. 随着研究深入, O-GlcNAc糖基化生物功能的系统解析需要更多特异、精准的研究工具和糖蛋白质组学研究策略. 近年来, 化学生物学领域开发了包括小分子糖探针、生物正交糖代谢标记物、化学酶法、特异性抗体和凝集素等多种O-GlcNAc糖基化分析工具和方法, 以此为基础进一步发展了O-GlcNAc糖蛋白质组学研究策略. 同时, 借助高分辨质谱, 大量蛋白质O-GlcNAc修饰位点得以鉴定, 极大促进了位点特异性O-GlcNAc的生物功能研究. 本文综述了近年来这一领域的研究进展, 以期为更多化学工具的开发提供依据, 为揭示O-GlcNAc糖基化在疾病演进中的功能提供新的研究思路和策略.

关键词: O-GlcNAc糖基化, 化学生物学, 分子工具, 糖蛋白质组学

The addition of O-linked-β-N-acetylglucosamine (O-GlcNAc) onto serine and threonine residues of nuclear and cytoplasmic proteins is an abundant and unique post-translational modification that plays a critical role in governing important biological processes. Since its discovery, O-GlcNAcylation has been shown to contribute to numerous cellular processes, including signaling, protein localization and stability, transcription, chromatin remodeling, mitochondrial function, and cell survival. O-GlcNAcylation is a dynamic and reversible post-translational modification that regulates protein function in a site-specific manner, making it an important player in the regulation of diverse biological processes. Dysregulation of O-GlcNAcylation has been implicated in the pathogenesis of various diseases, including cancer, neurodegenerative disorders, and diabetes. To better understand the regulatory roles of O-GlcNAcylation in cellular physiology and disease pathogenesis, O-GlcNAc proteomics strategies and more specialized, more exact research tools are needed to further explore the bio-functional systematization of O-GlcNAcylation. In recent years, the field of chemical biology has developed various tools and methods for analyzing O-GlcNAc glycosylation, including small molecule sugar probes, metabolic labeling reagents, chemoenzymatic techniques, specific antibodies, and lectins. These tools have served as a foundation for the further development of O-GlcNAc glycoproteomic research strategies. O-GlcNAc glycoproteomic strategies, such as high-resolution mass spectrometry-based approaches have been developed to allow for the detection and quantification of O-GlcNAc modifications on specific proteins, enabling site-specific analysis of O-GlcNAc modification patterns. The number of proteins modified by O-GlcNAc is quite extensive, with at least 7000 modification sites identified in human cells. This highlights the importance of O-GlcNAcylation in regulating diverse biological processes. Identification of O-GlcNAcylation sites with specific biological functions is still a remaining problem. Innovative solutions are required to address this challenge in cell models and disease therapy. At the same time, with the aid of high-resolution mass spectrometry, a large number of O-GlcNAc modification sites on proteins have been identified, which has greatly promoted the study of site-specific O-GlcNAc biological functions. This article has reviewed the recent advances in the field of O-GlcNAc research, with the aim of providing a basis for the development of more chemical tools and offering new research ideas and strategies for uncovering the functions of O-GlcNAcylation in disease progression.

Key words: O-GlcNAcylation, chemical biology, molecular tools, glycoproteomics

引用此文

张娜娜, 于恺然, 李际婷, 张嘉宁, 刘宇博. 化学生物学解析疾病中O-GlcNAc糖基化功能: 研究工具与策略[J]. 化学学报, 2023, 81(7): 843-856.

Nana Zhang, Kairan Yu, Jiting Li, Jianing Zhang, Yubo Liu. Application of Chemical Biology to Reveal the Function of O-GlcNAcylation in Diseases: Research Tools and Tactics[J]. Acta Chimica Sinica, 2023, 81(7): 843-856.

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图/表 9

图1. O-GlcNAc糖基化调控多种细胞功能和生理过程. S: 丝氨酸; T: 苏氨酸. HBP: 己糖胺合成途径

Figure 1. O-GlcNAcylation regulates various cellular functions and physiological processes. S: serine; T: threonine. HBP: hexosamine biosynthetic pathway

图2. OGT抑制剂类O-GlcNAc糖探针化学结构. (a) UDP以及UDP-GlcNAc类似物O-GlcNAc糖探针. (b)高通量筛选获得的O-GlcNAc糖探针

Figure 2. Chemical structures of OGT inhibitor-related O-GlcNAc molecular probes. (a) UDP and UDP-GlcNAc analog O-GlcNAc molecular probes. (b) O-GlcNAc molecular probes obtained by high-throughput screening

OGT抑制剂	抑制性参数	优点	缺点
Alloxan	IC₅₀=100 μmol/L	细胞渗透性好	选择性差
Ac-5SGlcNAc	EC₅₀=5 μmol/L	选择性好	脱靶, 水溶性差
5SGlcNAc	与Ac-5SGlcNAc近似	选择性好, 细胞渗透性好	未知
5S-GlcNHex	IC₅₀=11 μmol/L	水溶性、细胞渗透力强	同时抑制其它糖基转移酶
Goblin	IC₅₀=18 μmol/L	—	细胞渗透性差, 无法体内实验
OSMI-1	IC₅₀=2.7 μmol/L	细胞渗透性、选择性好	降低细胞活力, 脱靶效应
OSMI-2, OSMI-3, OSMI-4	OSMI-2 IC₅₀= 140 nmol/L OSMI-3 IC₅₀=5 nmol/L OSMI-4 IC₅₀=8 nmol/L	抑制效果好	未知
L01	IC₅₀=21.8 μmol/L	细胞可渗透, 天然产物, 低毒性	脱靶效应
APNT, APBT	APNT: IC₅₀=66.7 μmol/L APBT IC₅₀=139 μmol/L	细胞可渗透, 非竞争抑制, 低毒性	水中溶解性差, 效力低
LQMed 330	IC₅₀=11.7 μmol/L	未知	选择性差, 溶解性和渗透性未知

表1. OGT抑制剂类O-GlcNAc糖探针及特性

Table 1. Characteristics of OGT inhibitor-related O-GlcNAcylation molecular probes

图3. OGA抑制剂类O-GlcNAc糖探针化学结构

Figure 3. Chemical structures of OGT inhibitor-related O-GlcNAcylation molecular probes

O-GlcNAc抗体	抗原	抗体	应用范围
RL2	CTSPPDS (O-GlcNAc) SVIVTLLD	IgG	免疫印迹、免疫荧光、酶联免疫
CTD110.6	VYKSPVVS (O-GlcNAc) GDTSPRH	IgM	免疫印迹、免疫组化
HGAC85	KKFELLPT (O-GlcNAc) PPLSPSRR	IgG	免疫印迹、免疫组化、免疫沉淀、酶联免疫、免疫细胞化学、染色质免疫沉淀
EPR19847	CDTSPAAPVS (O-GlcNAc) YADMRTGI	IgG	免疫印记、免疫沉淀、点杂交

表2. 代表性O-GlcNAc修饰特异性抗体的特性

Table 2. Parameters of several O-GlcNAcylation specific antibodies

图4. 几种代表性的O-GlcNAc代谢标记分子化学结构

Figure 4. Chemical structures of several representative O-GlcNAcylation metabolic labeling molecules

图5. O-GlcNAc糖代谢标记和化学酶法标记流程

Figure 5. Process of metabolic labeling and chemoenzymatic labeling of O-GlcNAcylation

图6. 可剪切生物素探针化学结构

Figure 6. Chemical structures of cleavable alkyne-biotin probes

图7. O-GlcNAc糖基化位点特异性功能研究策略. (a)酶催化的蛋白质O-GlcNAc修饰过程. (b)、(c) O-GlcNAc特异性位点突变和人工S-GlcNAc糖基化. (d)通过纳米抗体/标签将OGT催化结构域靶向蛋白质, 标记靶蛋白. 添加O-GlcNAc修饰. OGA纳米抗体可以靶向去除O-GlcNAc修饰

Figure 7. Several strategies used in site-specific research of O-GlcNAcylation. (a) Enzyme-catalyzed protein O-GlcNAcylation process. (b), (c) Site-directed mutagenesis and S-Glycosylation enables O-GlcNAc engineering at a specific site. (d) Targeting OGT catalytic domains to proteins through nanoantibodies or tags, labeling target proteins and adding O-GlcNAc modification. Similarly, OGA can be a nanoantibody targeted to remove O-GlcNAc

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