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本文引用的文献

1
(Glycan Binding) Activity-Based Protein Profiling in Cells Enabled by Mass Spectrometry-Based Proteomics.基于质谱蛋白质组学的细胞中基于聚糖结合活性的蛋白质谱分析
Isr J Chem. 2023 Mar;63(3-4). doi: 10.1002/ijch.202200097. Epub 2023 Jan 18.
2
Chemoproteomic mapping of human milk oligosaccharide (HMO) interactions in cells.人乳寡糖（HMO）在细胞中相互作用的化学蛋白质组学图谱分析
RSC Chem Biol. 2022 Oct 18;3(12):1369-1374. doi: 10.1039/d2cb00176d. eCollection 2022 Nov 30.
3
Stereoselective β-mannosylations and β-rhamnosylations from glycosyl hemiacetals mediated by lithium iodide.由碘化锂介导的从糖基半缩醛进行的立体选择性β-甘露糖基化和β-鼠李糖基化反应。
Chem Sci. 2021 Jul 5;12(29):10070-10075. doi: 10.1039/d1sc01300a. eCollection 2021 Jul 28.
4
Chemoproteomic-enabled phenotypic screening.基于化学蛋白质组学的表型筛选。
Cell Chem Biol. 2021 Mar 18;28(3):371-393. doi: 10.1016/j.chembiol.2021.01.012. Epub 2021 Feb 11.
5
Activation of the G-protein coupled receptor GPR35 by human milk oligosaccharides through different pathways.人乳寡糖通过不同途径激活 G 蛋白偶联受体 GPR35。
Sci Rep. 2020 Sep 30;10(1):16117. doi: 10.1038/s41598-020-73008-0.
6
Photoaffinity Probes for the Identification of Sequence-Specific Glycosaminoglycan-Binding Proteins.用于鉴定序列特异性糖胺聚糖结合蛋白的光亲和探针。
J Am Chem Soc. 2020 Aug 12;142(32):13672-13676. doi: 10.1021/jacs.0c06046. Epub 2020 Aug 3.
7
Photocrosslinking probes for capture of carbohydrate interactions.用于捕获碳水化合物相互作用的光交联探针。
Curr Opin Chem Biol. 2019 Dec;53:173-182. doi: 10.1016/j.cbpa.2019.09.002. Epub 2019 Nov 6.
8
Novel NMR Avenues to Explore the Conformation and Interactions of Glycans.探索聚糖构象与相互作用的新型核磁共振途径
ACS Omega. 2019 Aug 19;4(9):13618-13630. doi: 10.1021/acsomega.9b01901. eCollection 2019 Aug 27.
9
A bioactive mammalian disaccharide associated with autoimmunity activates STING-TBK1-dependent immune response.一种与自身免疫相关的生物活性哺乳动物二糖激活 STING-TBK1 依赖性免疫反应。
Nat Commun. 2019 May 30;10(1):2377. doi: 10.1038/s41467-019-10319-5.
10
Influence of remote functional groups towards the formation of 1,2-cis glycosides: special emphasis on β-mannosylation.远程官能团对 1,2-顺式糖苷形成的影响：特别强调β-甘露糖基化。
Org Biomol Chem. 2019 May 8;17(18):4605-4610. doi: 10.1039/c9ob00670b.

基于Man(β1,4)GlcNAc的光可激活生物正交探针的立体选择性合成。

Stereoselective synthesis of photoactivatable Man(β1,4)GlcNAc-based bioorthogonal probes.

作者信息

Hassan Abdullah A, Huang Mia L

机构信息

Department of Molecular Medicine and Department of Chemistry, Scripps Research, 10550 N. Torrey Pines Rd., La Jolla, CA 92037.

Skaggs Graduate School of Chemical and Biological Sciences, Scripps Research, 10550 N. Torrey Pines Rd., La Jolla, CA 92037.

出版信息

Tetrahedron Lett. 2023 Jun 6;122. doi: 10.1016/j.tetlet.2023.154521. Epub 2023 May 5.

DOI:10.1016/j.tetlet.2023.154521
PMID:37274137
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10237449/
Abstract

We report an operationally facile protocol to prepare photoactivatable probes of the bioactive mammalian disaccharide, Man(β1,4)GlcNAc. Using conformationally restricted mannosyl hemi-acetal donors in a one-pot chlorination, iodination and glycosylation sequence, β-mannosides were generated in excellent diastereoselectivities and yields. Upon accessing the disaccharide, we generated the corresponding photoactivatable probes by appending a diazirine-alkyne equipped linker via a condensation reaction between a diazirine-containing linker and C-1 and C-2 derivatized mannosylamines to furnish the desired C-1 and C-2 modified Man(β1,4)GlcNAc-based probes. This new synthetic protocol greatly simplifies the preparation of this important bioactive disaccharide to enable future work to identify its protein binding partners in cells.

摘要

我们报道了一种操作简便的方法来制备具有生物活性的哺乳动物二糖Man(β1,4)GlcNAc的光活化探针。在一锅法氯化、碘化和糖基化序列中使用构象受限的甘露糖基半缩醛供体，以优异的非对映选择性和产率生成了β-甘露糖苷。在获得二糖后，我们通过含重氮环丙烷的连接子与C-1和C-2衍生化的甘露糖胺之间的缩合反应，连接一个重氮环丙烷-炔基连接子，生成相应的光活化探针，以提供所需的基于C-1和C-2修饰的Man(β1,4)GlcNAc的探针。这种新的合成方法极大地简化了这种重要生物活性二糖的制备，以便未来能够在细胞中鉴定其蛋白质结合伙伴。