研究细菌的N-连接糖基化：十一异戊二烯焦磷酸连接的芽孢胺的合成及糖基受体活性
Investigating bacterial N-linked glycosylation: synthesis and glycosyl acceptor activity of the undecaprenyl pyrophosphate-linked bacillosamine.
作者信息
Weerapana Eranthie, Glover Kerney Jebrell, Chen Mark M, Imperiali Barbara
机构信息
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
出版信息
J Am Chem Soc. 2005 Oct 12;127(40):13766-7. doi: 10.1021/ja054265v.
Abstract
The chemical synthesis and biological activity of undecaprenyl pyrophosphate bacillosamine (Und-PP-Bac), an obligatory intermediate in the asparagine-linked glycosylation pathway of Campylobacter jejuni, are reported. The key transformation involves the coupling of bacillosamine phosphate and undecaprenyl phosphate. The synthetic Und-PP-Bac can be used to investigate the activity of the enzyme PglA, which catalyzes the first glycosyl transfer in substrate biosynthesis for N-linked protein glycosylation in the pathogenic gram-negative bacterium. The availability of this synthetic substrate makes it possible to access polyprenyl-linked oligosaccharides, such as the GalNAc-alpha-1,3-bacillosamine-alpha-1-PP-Und intermediate, that will enable exploration of the remaining enzymes in the prokaryotic glycosylation pathway. Study of the bacterial glycosylation system will provide insight into the corresponding eukaryotic process, which is currently poorly understood.
摘要
报道了空肠弯曲菌天冬酰胺连接糖基化途径中的必需中间体——十一异戊烯基焦磷酸杆菌胺（Und-PP-Bac）的化学合成及生物活性。关键转化步骤涉及磷酸杆菌胺与磷酸十一异戊烯酯的偶联。合成的Und-PP-Bac可用于研究PglA酶的活性，该酶催化致病性革兰氏阴性菌N-连接蛋白糖基化底物生物合成中的首次糖基转移。这种合成底物的可得性使得获取多聚异戊烯基连接的寡糖成为可能，比如GalNAc-α-1,3-杆菌胺-α-1-PP-Und中间体，这将有助于探索原核糖基化途径中的其余酶。对细菌糖基化系统的研究将为目前了解甚少的相应真核过程提供深入见解。
相似文献
1
Investigating bacterial N-linked glycosylation: synthesis and glycosyl acceptor activity of the undecaprenyl pyrophosphate-linked bacillosamine.研究细菌的N-连接糖基化：十一异戊二烯焦磷酸连接的芽孢胺的合成及糖基受体活性
J Am Chem Soc. 2005 Oct 12;127(40):13766-7. doi: 10.1021/ja054265v.
2
Direct biochemical evidence for the utilization of UDP-bacillosamine by PglC, an essential glycosyl-1-phosphate transferase in the Campylobacter jejuni N-linked glycosylation pathway.空肠弯曲菌N-连接糖基化途径中一种必需的糖基-1-磷酸转移酶PglC利用UDP-杆菌胺的直接生化证据。
Biochemistry. 2006 Apr 25;45(16):5343-50. doi: 10.1021/bi0602056.
3
In vitro assembly of the undecaprenylpyrophosphate-linked heptasaccharide for prokaryotic N-linked glycosylation.用于原核生物N-连接糖基化的十一异戊烯基焦磷酸连接的七糖的体外组装。
Proc Natl Acad Sci U S A. 2005 Oct 4;102(40):14255-9. doi: 10.1073/pnas.0507311102. Epub 2005 Sep 26.
4
Synthesis of asparagine-linked bacillosamine.天冬酰胺连接的芽孢胺的合成
Carbohydr Res. 2006 Aug 14;341(11):1922-9. doi: 10.1016/j.carres.2006.04.031. Epub 2006 May 15.
5
N-Glycosylation with synthetic undecaprenyl pyrophosphate-linked oligosaccharide to oligopeptides by PglB oligosaccharyltransferase from Campylobacter jejuni.空肠弯曲杆菌的PglB寡糖基转移酶利用合成的十一异戊烯基焦磷酸连接的寡糖对寡肽进行N-糖基化。
Chembiochem. 2015 Mar 23;16(5):731-7. doi: 10.1002/cbic.201402658. Epub 2015 Feb 16.
6
Chemoenzymatic synthesis of polyprenyl phosphates.聚异戊二烯磷酸酯的化学酶法合成。
Bioorg Med Chem. 2008 May 1;16(9):5149-56. doi: 10.1016/j.bmc.2008.03.025. Epub 2008 Mar 14.
7
Development of a multicomponent kinetic assay of the early enzymes in the Campylobacter jejuni N-linked glycosylation pathway.开发空肠弯曲菌 N-连接糖基化途径早期酶的多组分动力学测定法。
Bioorg Med Chem. 2010 Dec 1;18(23):8167-71. doi: 10.1016/j.bmc.2010.10.020. Epub 2010 Oct 29.
8
Chemoenzymatic synthesis of the bacterial polysaccharide repeating unit undecaprenyl pyrophosphate and its analogs.酶促化学合成细菌多糖十一异戊烯焦磷酸重复单元及其类似物。
Nat Protoc. 2016 Jul;11(7):1280-98. doi: 10.1038/nprot.2016.067. Epub 2016 Jun 23.
9
Chemoenzymatic synthesis of glycopeptides with PglB, a bacterial oligosaccharyl transferase from Campylobacter jejuni.利用空肠弯曲菌的细菌寡糖基转移酶PglB进行糖肽的化学酶法合成。
Chem Biol. 2005 Dec;12(12):1311-5. doi: 10.1016/j.chembiol.2005.10.004.
10
An Escherichia coli undecaprenyl-pyrophosphate phosphatase implicated in undecaprenyl phosphate recycling.一种参与磷酸十一碳烯醇循环的大肠杆菌十一碳烯基焦磷酸磷酸酶。
Microbiology (Reading). 2007 Aug;153(Pt 8):2518-2529. doi: 10.1099/mic.0.2007/006312-0.
引用本文的文献
1
Characterization of PglJ, a Glycosyltransferase in the N-Linked Protein Glycosylation Pathway that Expands Glycan Diversity.鉴定 PglJ，一种 N-连接蛋白糖基化途径中的糖基转移酶，可扩展聚糖多样性。
Biochemistry. 2024 Jan 2;63(1):141-151. doi: 10.1021/acs.biochem.3c00564. Epub 2023 Dec 18.
2
Sulfamate-Tethered Aza-Wacker Strategy for a Kasugamine Synthon.用于春日胺合成子的氨磺酸盐连接的氮杂瓦克反应策略。
J Org Chem. 2024 Jan 5;89(1):793-797. doi: 10.1021/acs.joc.3c02292. Epub 2023 Dec 8.
3
Synthetic Approach to 2,4-Diamino-2,4,6-trideoxyhexoses (DATDH): Bacterial and Rare Deoxy-Amino Sugars.合成 2,4-二氨基-2,4,6-三脱氧己糖（DATDH）的方法：细菌和罕见的脱氧-氨基糖。
Org Lett. 2023 Nov 3;25(43):7873-7877. doi: 10.1021/acs.orglett.3c03106. Epub 2023 Oct 20.
4
Structural and mechanistic studies of the N-glycosylation machinery: from lipid-linked oligosaccharide biosynthesis to glycan transfer.糖基化工程结构与机制研究：从脂连接寡糖生物合成到聚糖转移。
Glycobiology. 2023 Dec 25;33(11):861-872. doi: 10.1093/glycob/cwad053.
5
Synthesis of selected unnatural sugar nucleotides for biotechnological applications.用于生物技术应用的选定非天然糖核苷酸的合成。
Crit Rev Biotechnol. 2021 Feb;41(1):47-62. doi: 10.1080/07388551.2020.1844623. Epub 2020 Nov 5.
6
Chemoenzymatic Methods for the Synthesis of Glycoproteins.糖蛋白的化学酶法合成。
Chem Rev. 2018 Sep 12;118(17):8359-8413. doi: 10.1021/acs.chemrev.8b00238. Epub 2018 Aug 24.
7
Chemical Synthesis of Rare, Deoxy-Amino Sugars Containing Bacterial Glycoconjugates as Potential Vaccine Candidates.稀有去氧氨基糖的化学合成，包含细菌糖缀合物作为潜在疫苗候选物。
Molecules. 2018 Aug 10;23(8):1997. doi: 10.3390/molecules23081997.
8
Structural basis of the molecular ruler mechanism of a bacterial glycosyltransferase.细菌糖基转移酶分子尺机制的结构基础。
Nat Commun. 2018 Jan 31;9(1):445. doi: 10.1038/s41467-018-02880-2.
9
Synthesis of 4-Azido-N-acetylhexosamine Uridine Diphosphate Donors: Clickable Glycosaminoglycans.合成 4-叠氮基-N-乙酰己糖胺尿苷二磷酸供体：可点击糖胺聚糖。
J Org Chem. 2017 Sep 15;82(18):9910-9915. doi: 10.1021/acs.joc.7b01787. Epub 2017 Aug 25.
10
Bacterial phosphoglycosyl transferases: initiators of glycan biosynthesis at the membrane interface.细菌磷酸糖基转移酶：膜界面聚糖生物合成的起始者。
Glycobiology. 2017 Sep 1;27(9):820-833. doi: 10.1093/glycob/cwx064.
本文引用的文献
1
In vitro assembly of the undecaprenylpyrophosphate-linked heptasaccharide for prokaryotic N-linked glycosylation.用于原核生物N-连接糖基化的十一异戊烯基焦磷酸连接的七糖的体外组装。
Proc Natl Acad Sci U S A. 2005 Oct 4;102(40):14255-9. doi: 10.1073/pnas.0507311102. Epub 2005 Sep 26.
2
Functional analysis of the Campylobacter jejuni N-linked protein glycosylation pathway.空肠弯曲菌N-连接蛋白糖基化途径的功能分析。
Mol Microbiol. 2005 Mar;55(6):1695-703. doi: 10.1111/j.1365-2958.2005.04519.x.
3
Protein glycosylation in bacterial mucosal pathogens.细菌黏膜病原体中的蛋白质糖基化
Nat Rev Microbiol. 2005 Mar;3(3):225-37. doi: 10.1038/nrmicro1100.
4
The N-X-S/T consensus sequence is required but not sufficient for bacterial N-linked protein glycosylation.N-X-S/T共有序列是细菌N-连接蛋白糖基化所必需的，但并不充分。
Glycobiology. 2005 Apr;15(4):361-7. doi: 10.1093/glycob/cwi019. Epub 2004 Dec 1.
5
N-linked glycosylation in Campylobacter jejuni and its functional transfer into E. coli.空肠弯曲菌中的N-连接糖基化及其向大肠杆菌的功能转移。
Science. 2002 Nov 29;298(5599):1790-3. doi: 10.1126/science.298.5599.1790.
6
Structure of the N-linked glycan present on multiple glycoproteins in the Gram-negative bacterium, Campylobacter jejuni.空肠弯曲杆菌（Campylobacter jejuni）中多种糖蛋白上存在的N-连接聚糖的结构。
J Biol Chem. 2002 Nov 8;277(45):42530-9. doi: 10.1074/jbc.M206114200. Epub 2002 Aug 16.
7
Better substrates for bacterial transglycosylases.更适合细菌转糖基酶的底物。
J Am Chem Soc. 2001 Apr 4;123(13):3155-6. doi: 10.1021/ja010028q.
8
Evidence for a system of general protein glycosylation in Campylobacter jejuni.空肠弯曲杆菌中存在一般蛋白质糖基化系统的证据。
Mol Microbiol. 1999 Jun;32(5):1022-30. doi: 10.1046/j.1365-2958.1999.01415.x.
9
The dolichol pathway of N-linked glycosylation.N-连接糖基化的多萜醇途径。
Biochim Biophys Acta. 1999 Jan 6;1426(2):239-57. doi: 10.1016/s0304-4165(98)00127-5.
10
Synthesis of 2-acetamido-2-deoxy-1-thio-beta-D-glucopyranosides.2-乙酰氨基-2-脱氧-1-硫代-β-D-吡喃葡萄糖苷的合成
Carbohydr Res. 1973 Oct;30(2):414-7. doi: 10.1016/s0008-6215(00)81833-9.
Zotero 插件