Highly efficient synthesis of UDP-GalNAc/GlcNAc analogues with promiscuous recombinant human UDP-GalNAc pyrophosphorylase AGX1.
作者信息
Guan Wanyi, Cai Li, Wang Peng George
机构信息
Department of Chemistry and Biochemistry, The Ohio State University, 484 West 12th Avenue, Columbus, OH 43210, USA.
出版信息
Chemistry. 2010 Dec 3;16(45):13343-5. doi: 10.1002/chem.201002315.
Abstract
摘要
相似文献
1
Highly efficient synthesis of UDP-GalNAc/GlcNAc analogues with promiscuous recombinant human UDP-GalNAc pyrophosphorylase AGX1.利用混杂的重组人UDP-N-乙酰半乳糖胺焦磷酸化酶AGX1高效合成UDP-N-乙酰半乳糖胺/ N-乙酰葡糖胺类似物。
Chemistry. 2010 Dec 3;16(45):13343-5. doi: 10.1002/chem.201002315.
2
Investigation of the nucleotide triphosphate substrate specificity of Homo sapiens UDP-N-acetylgalactosamine pyrophosphorylase (AGX1).人源 UDP-N-乙酰氨基半乳糖胺焦磷酸化酶（AGX1）的核苷酸三磷酸底物特异性研究。
Bioorg Med Chem Lett. 2012 Jun 15;22(12):3957-61. doi: 10.1016/j.bmcl.2012.04.102. Epub 2012 Apr 28.
3
A 17-amino acid insert changes UDP-N-acetylhexosamine pyrophosphorylase specificity from UDP-GalNAc to UDP-GlcNAc.一段17个氨基酸的插入序列将UDP-N-乙酰己糖胺焦磷酸化酶的特异性从UDP-GalNAc改变为UDP-GlcNAc。
J Biol Chem. 1998 Oct 16;273(42):27055-7. doi: 10.1074/jbc.273.42.27055.
4
Synthesis of novel donor mimetics of UDP-Gal, UDP-GlcNAc, and UDP-GalNAc as potential transferase inhibitors.新型UDP - 半乳糖、UDP - N - 乙酰葡糖胺和UDP - N - 乙酰半乳糖胺供体模拟物的合成作为潜在的转移酶抑制剂。
J Org Chem. 2000 Jan 14;65(1):24-9. doi: 10.1021/jo990766l.
5
Two-step enzymatic synthesis of UDP-N-acetylgalactosamine.UDP-N-乙酰半乳糖胺的两步酶促合成
Bioorg Med Chem Lett. 2005 Dec 15;15(24):5459-62. doi: 10.1016/j.bmcl.2005.08.088. Epub 2005 Oct 3.
6
Chemoenzymatic synthesis of uridine diphosphate-GlcNAc and uridine diphosphate-GalNAc analogs for the preparation of unnatural glycosaminoglycans.酶促化学合成尿苷二磷酸-N-乙酰葡糖胺和尿苷二磷酸-N-乙酰半乳糖胺类似物用于制备非天然糖胺聚糖。
J Org Chem. 2012 Feb 3;77(3):1449-56. doi: 10.1021/jo202322k. Epub 2012 Jan 12.
7
Amino sugar phosphate levels in Giardia change during cyst wall formation.贾第虫中氨基糖磷酸水平在包囊壁形成过程中会发生变化。
Microbiology (Reading). 2004 May;150(Pt 5):1225-1230. doi: 10.1099/mic.0.26898-0.
8
New UDP-GlcNAc C4 epimerase involved in the biosynthesis of 2-acetamino-2-deoxy-L-altruronic acid in the O-antigen repeating units of Plesiomonas shigelloides O17.参与弗氏志贺菌O17 O抗原重复单元中2-乙酰氨基-2-脱氧-L-阿卓糖醛酸生物合成的新型UDP-N-乙酰葡糖胺C4差向异构酶
Biochemistry. 2002 Dec 24;41(51):15410-4. doi: 10.1021/bi026384i.
9
Identification and modification of the uridine-binding site of the UDP-GalNAc (GlcNAc) pyrophosphorylase.UDP-N-乙酰半乳糖胺（GlcNAc）焦磷酸化酶尿苷结合位点的鉴定与改造。
J Biol Chem. 2000 Jan 14;275(2):1433-8. doi: 10.1074/jbc.275.2.1433.
10
Efficient chemoenzymatic synthesis of uridine 5'-diphosphate N-acetylglucosamine and uridine 5'-diphosphate N-trifluoacetyl glucosamine with three recombinant enzymes.利用三种重组酶高效化学酶法合成5'-二磷酸尿苷-N-乙酰葡糖胺和5'-二磷酸尿苷-N-三氟乙酰葡糖胺
Prep Biochem Biotechnol. 2017 Oct 21;47(9):852-859. doi: 10.1080/10826068.2016.1188315. Epub 2016 May 24.
引用本文的文献
1
Protein β-O-glucosylation by Legionella LtpM through short consensus sequons G-T/S and S-G.嗜肺军团菌LtpM通过短共有序列G-T/S和S-G对蛋白质进行β-O-葡萄糖基化修饰。
Nat Chem Biol. 2025 Jul 14. doi: 10.1038/s41589-025-01968-3.
2
Comprehensive Modular Synthesis of Ganglioside Glycans and Evaluation of their Binding Affinities to Siglec-7 and Siglec-9.神经节苷脂聚糖的综合模块化合成及其与唾液酸结合免疫球蛋白样凝集素-7和唾液酸结合免疫球蛋白样凝集素-9结合亲和力的评估
Adv Sci (Weinh). 2025 Jan;12(2):e2412815. doi: 10.1002/advs.202412815. Epub 2024 Nov 18.
3
A Bioorthogonal Precision Tool for Human -Acetylglucosaminyltransferase V.一种用于人源N-乙酰葡糖胺基转移酶V的生物正交精密工具。
J Am Chem Soc. 2024 Oct 2;146(39):26707-26718. doi: 10.1021/jacs.4c05955. Epub 2024 Sep 17.
4
Biosynthetic production of anticoagulant heparin polysaccharides through metabolic and sulfotransferases engineering strategies.通过代谢和磺基转移酶工程策略的生物合成生产抗凝肝素多糖。
Nat Commun. 2024 May 4;15(1):3755. doi: 10.1038/s41467-024-48193-5.
5
A modular chemoenzymatic cascade strategy for the structure-customized assembly of ganglioside analogs.一种用于神经节苷脂类似物结构定制组装的模块化化学酶级联策略。
Commun Chem. 2024 Jan 18;7(1):17. doi: 10.1038/s42004-024-01102-9.
6
A concise chemoenzymatic total synthesis of neutral Globo-series glycosphingolipids Globo A and Globo B, and Forssman and para-Forssman antigens.中性 Globo 系列糖脂 Globo A 和 Globo B 以及 Forssman 和 para-Forssman 抗原的简明酶促全合成。
Glycoconj J. 2023 Oct;40(5):551-563. doi: 10.1007/s10719-023-10133-8. Epub 2023 Aug 22.
7
Novel β1,4 N-acetylglucosaminyltransferase in de novo enzymatic synthesis of hyaluronic acid oligosaccharides.新型β1,4-N-乙酰氨基葡萄糖基转移酶在透明质酸寡糖的从头酶法合成中的应用。
Appl Microbiol Biotechnol. 2023 Aug;107(16):5119-5129. doi: 10.1007/s00253-023-12671-5. Epub 2023 Jul 5.
8
Imaging of K5 and glycosaminoglycan precursors via targeted metabolic labeling of capsular polysaccharides in bacteria.通过靶向代谢标记细菌荚膜多糖来进行 K5 和糖胺聚糖前体的成像。
Sci Adv. 2023 Feb 17;9(7):eade4770. doi: 10.1126/sciadv.ade4770.
9
Metabolic labeling of the bacterial peptidoglycan by functionalized glucosamine.通过功能化葡糖胺对细菌肽聚糖进行代谢标记
iScience. 2022 Jul 12;25(8):104753. doi: 10.1016/j.isci.2022.104753. eCollection 2022 Aug 19.
10
General Tolerance of Galactosyltransferases toward UDP-galactosamine Expands Their Synthetic Capability.半乳糖基转移酶对 UDP-半乳糖胺的普遍耐受性扩展了它们的合成能力。
Angew Chem Int Ed Engl. 2021 Dec 13;60(51):26555-26560. doi: 10.1002/anie.202112574. Epub 2021 Nov 9.
本文引用的文献
1
Chemoenzymatic synthesis of uridine 5'-diphospho-2-acetonyl-2-deoxy-alpha-D-glucose as C(2)-carbon isostere of UDP-GlcNAc.通过酶促化学合成尿苷 5'-二磷酸-2-乙酰基-2-脱氧-α-D-葡萄糖作为 UDP-GlcNAc 的 C(2)-碳等排物。
J Org Chem. 2010 May 21;75(10):3492-4. doi: 10.1021/jo100385p.
2
Enzymatic route to preparative-scale synthesis of UDP-GlcNAc/GalNAc, their analogues and GDP-fucose.酶法制备 UDP-GlcNAc/GalNAc、其类似物和 GDP-Fuc 的大规模合成。
Nat Protoc. 2010 Apr;5(4):636-46. doi: 10.1038/nprot.2010.3. Epub 2010 Mar 11.
3
Enzymatic synthesis of UDP-GlcNAc/UDP-GalNAc analogs using N-acetylglucosamine 1-phosphate uridyltransferase (GlmU).使用 N-乙酰氨基葡萄糖 1-磷酸尿苷酰转移酶（GlmU）酶促合成 UDP-GlcNAc/UDP-GalNAc 类似物。
Chem Commun (Camb). 2009 Dec 7(45):6976-8. doi: 10.1039/b917573c. Epub 2009 Oct 20.
4
A survey of chemical methods for sugar-nucleotide synthesis.糖核苷酸合成化学方法综述。
Nat Prod Rep. 2009 Sep;26(9):1172-94. doi: 10.1039/b909621n. Epub 2009 Jul 27.
5
Substrate specificity of N-acetylhexosamine kinase towards N-acetylgalactosamine derivatives.N-乙酰己糖胺激酶对N-乙酰半乳糖胺衍生物的底物特异性。
Bioorg Med Chem Lett. 2009 Sep 15;19(18):5433-5. doi: 10.1016/j.bmcl.2009.07.104. Epub 2009 Jul 25.
6
A chemoenzymatic route to N-acetylglucosamine-1-phosphate analogues: substrate specificity investigations of N-acetylhexosamine 1-kinase.一条通往N-乙酰葡糖胺-1-磷酸类似物的化学酶法途径：N-乙酰己糖胺1-激酶的底物特异性研究
Chem Commun (Camb). 2009 May 28(20):2944-6. doi: 10.1039/b904853g. Epub 2009 Apr 24.
7
Natural-product sugar biosynthesis and enzymatic glycodiversification.天然产物糖生物合成与酶促糖多样化
Angew Chem Int Ed Engl. 2008;47(51):9814-59. doi: 10.1002/anie.200801204.
8
In vivo imaging of membrane-associated glycans in developing zebrafish.发育中斑马鱼膜相关聚糖的体内成像
Science. 2008 May 2;320(5876):664-7. doi: 10.1126/science.1155106.
9
Cycling of O-linked beta-N-acetylglucosamine on nucleocytoplasmic proteins.核质蛋白上O-连接的β-N-乙酰葡糖胺循环
Nature. 2007 Apr 26;446(7139):1017-22. doi: 10.1038/nature05815.
10
Artificial N-functionalized UDP-glucosamine analogues as modified substrates for N-acetylglucosaminyl transferases.
Carbohydr Res. 2006 Apr 10;341(5):569-76. doi: 10.1016/j.carres.2006.01.017. Epub 2006 Jan 30.
Zotero 插件