研究 YjiC 对 3-羟基黄酮的黄酮醇体外糖随机化作用。
Probing 3-hydroxyflavone for in vitro glycorandomization of flavonols by YjiC.
机构信息
Institute of Biomolecule Reconstruction (iBR), Department of Pharmaceutical Engineering, Sun Moon University, Tangjeong-myeon, Asan-si, Chungnam, Republic of Korea.
出版信息
Appl Environ Microbiol. 2013 Nov;79(21):6833-8. doi: 10.1128/AEM.02057-13. Epub 2013 Aug 23.
Abstract
The glycosylation of five different flavonols, fisetin, quercetin, myricetin, kaempferol, and 3-hydroxyflavone, was achieved by applying YjiC. 3-Hydroxyflavone was selected as a probe for in vitro glycorandomization of all flavonols using diverse nucleotide diphosphate-d/l-sugars. This study unlocked the possibilities of the glycodiversification of flavonols and the generation of novel compounds as future therapeutics.
摘要
五种不同的黄酮醇，即非瑟酮、槲皮素、杨梅素、山奈酚和 3-羟基黄酮，通过应用 YjiC 进行了糖基化。选择 3-羟基黄酮作为探针，使用不同的核苷酸二磷酸-d/l-糖，对所有黄酮醇进行体外糖基随机化。这项研究为黄酮醇的糖基多样化以及生成新化合物作为未来治疗方法提供了可能。
相似文献
1
Probing 3-hydroxyflavone for in vitro glycorandomization of flavonols by YjiC.研究 YjiC 对 3-羟基黄酮的黄酮醇体外糖随机化作用。
Appl Environ Microbiol. 2013 Nov;79(21):6833-8. doi: 10.1128/AEM.02057-13. Epub 2013 Aug 23.
2
Donor specificity of YjiC glycosyltransferase determines the conjugation of cytosolic NDP-sugar in in vivo glycosylation reactions.YjiC糖基转移酶的供体特异性决定了体内糖基化反应中胞质NDP-糖的结合。
Enzyme Microb Technol. 2016 Sep;91:26-33. doi: 10.1016/j.enzmictec.2016.05.006. Epub 2016 May 21.
3
Assessing acceptor substrate promiscuity of YjiC-mediated glycosylation toward flavonoids.评估YjiC介导的糖基化对黄酮类化合物的受体底物选择性。
Carbohydr Res. 2014 Jul 1;393:26-31. doi: 10.1016/j.carres.2014.03.011. Epub 2014 May 9.
4
Altering UDP-glucose Donor Substrate Specificity of Glycosyltransferase towards TDP-glucose.改变糖基转移酶对胸苷二磷酸葡萄糖（TDP - 葡萄糖）的尿苷二磷酸葡萄糖（UDP - 葡萄糖）供体底物特异性。
J Microbiol Biotechnol. 2019 Feb 28;29(2):268-273. doi: 10.4014/jmb.1811.11009.
5
Enzymatic synthesis of novel phloretin glucosides.新型根皮苷葡萄糖苷的酶法合成。
Appl Environ Microbiol. 2013 Jun;79(11):3516-21. doi: 10.1128/AEM.00409-13. Epub 2013 Mar 29.
6
Formation of flavone di-O-glucosides using a glycosyltransferase from Bacillus cereus.利用蜡样芽孢杆菌的糖基转移酶形成黄酮二 - O - 葡萄糖苷。
J Microbiol Biotechnol. 2009 Apr;19(4):387-90. doi: 10.4014/jmb.0802.116.
7
Genetic engineering approach for the production of rhamnosyl and allosyl flavonoids from Escherichia coli.从大肠杆菌中生产鼠李糖基和阿洛糖基类黄酮的遗传工程方法。
Biotechnol Bioeng. 2010 Sep 1;107(1):154-62. doi: 10.1002/bit.22782.
8
Metabolic engineering of Escherichia coli into a versatile glycosylation platform: production of bio-active quercetin glycosides.将大肠杆菌代谢工程改造为通用糖基化平台：生物活性槲皮素糖苷的生产。
Microb Cell Fact. 2015 Sep 16;14:138. doi: 10.1186/s12934-015-0326-1.
9
Crystal structures of glycosyltransferase UGT78G1 reveal the molecular basis for glycosylation and deglycosylation of (iso)flavonoids.糖基转移酶UGT78G1的晶体结构揭示了（异）黄酮糖基化和去糖基化的分子基础。
J Mol Biol. 2009 Oct 9;392(5):1292-302. doi: 10.1016/j.jmb.2009.08.017. Epub 2009 Aug 13.
10
Exploiting the aglycon promiscuity of glycosyltransferase Bs-YjiC from Bacillus subtilis and its application in synthesis of glycosides.利用枯草芽孢杆菌糖基转移酶Bs-YjiC的苷元选择性及其在糖苷合成中的应用。
J Biotechnol. 2017 Apr 20;248:69-76. doi: 10.1016/j.jbiotec.2017.03.009. Epub 2017 Mar 16.
引用本文的文献
1
Dietary flavonoid fisetin binds human SUMO1 and blocks sumoylation of p53.饮食类黄酮非瑟酮与人 SUMO1 结合并阻断 p53 的 sumoylation。
PLoS One. 2020 Jun 12;15(6):e0234468. doi: 10.1371/journal.pone.0234468. eCollection 2020.
2
Exploring the Nucleophilic - and -Glycosylation Capacity of YjiC Enzyme.探索 YjiC 酶的亲核 - 和 - 糖苷化能力。
J Microbiol Biotechnol. 2020 Jul 28;30(7):1092-1096. doi: 10.4014/jmb.2001.01024.
3
Recent Advances in the Metabolic Engineering of Yeasts for Ginsenoside Biosynthesis.酵母代谢工程用于人参皂苷生物合成的最新进展
Front Bioeng Biotechnol. 2020 Feb 25;8:139. doi: 10.3389/fbioe.2020.00139. eCollection 2020.
4
Biocatalytic Synthesis of Non-Natural Monoterpene -Glycosides Exhibiting Superior Antibacterial and Antinematodal Properties.具有卓越抗菌和抗线虫特性的非天然单萜糖苷的生物催化合成。
ACS Omega. 2019 May 29;4(5):9367-9375. doi: 10.1021/acsomega.9b00535. eCollection 2019 May 31.
5
Glycosylation of 3-Hydroxyflavone, 3-Methoxyflavone, Quercetin and Baicalein in Fungal Cultures of the Genus .3-羟基黄酮、3-甲氧基黄酮、槲皮素和黄芩素在.属真菌培养物中的糖基化
Molecules. 2018 Sep 27;23(10):2477. doi: 10.3390/molecules23102477.
6
Enzymatic synthesis of lactosylated and sialylated derivatives of epothilone A.埃坡霉素A的乳糖基化和唾液酸化衍生物的酶促合成
Glycoconj J. 2016 Apr;33(2):137-46. doi: 10.1007/s10719-015-9646-y. Epub 2016 Feb 6.
7
Modification of emodin and aloe-emodin by glycosylation in engineered Escherihia coli.工程化大肠杆菌中大黄素和芦荟大黄素的糖基化修饰
World J Microbiol Biotechnol. 2015 Apr;31(4):611-9. doi: 10.1007/s11274-015-1815-4. Epub 2015 Feb 7.
8
Excited state proton transfer of natural flavonoids and their chromophores in duplex and tetraplex DNAs.天然黄酮类化合物及其发色团在双链和四链DNA中的激发态质子转移
J Phys Chem B. 2015 Feb 12;119(6):2546-56. doi: 10.1021/jp508599h. Epub 2014 Nov 13.
9
Enzymatic Biosynthesis of Novel Resveratrol Glucoside and Glycoside Derivatives.新型白藜芦醇糖苷和糖苷衍生物的酶促生物合成
Appl Environ Microbiol. 2014 Dec;80(23):7235-43. doi: 10.1128/AEM.02076-14. Epub 2014 Sep 19.
10
Enzymatic glycosylation of the topical antibiotic mupirocin.局部用抗生素莫匹罗星的酶促糖基化作用。
Glycoconj J. 2014 Nov;31(8):563-72. doi: 10.1007/s10719-014-9538-6. Epub 2014 Jul 30.
本文引用的文献
1
Enzymatic synthesis of novel phloretin glucosides.新型根皮苷葡萄糖苷的酶法合成。
Appl Environ Microbiol. 2013 Jun;79(11):3516-21. doi: 10.1128/AEM.00409-13. Epub 2013 Mar 29.
2
Production of 3-O-xylosyl quercetin in Escherichia coli.在大肠杆菌中生产 3-O-木糖基槲皮素。
Appl Microbiol Biotechnol. 2013 Mar;97(5):1889-901. doi: 10.1007/s00253-012-4438-9. Epub 2012 Oct 5.
3
Enzymatic glycosylation of nonbenzoquinone geldanamycin analogs via Bacillus UDP-glycosyltransferase.通过芽孢杆菌 UDP-糖基转移酶对非苯醌格尔德霉素类似物进行酶糖基化。
Appl Environ Microbiol. 2012 Nov;78(21):7680-6. doi: 10.1128/AEM.02004-12. Epub 2012 Aug 24.
4
Production of a novel quercetin glycoside through metabolic engineering of Escherichia coli.通过大肠杆菌代谢工程生产新型槲皮素糖苷。
Appl Environ Microbiol. 2012 Jun;78(12):4256-62. doi: 10.1128/AEM.00275-12. Epub 2012 Apr 6.
5
Facile syntheses of 3-hydroxyflavones.3-羟基黄酮的简便合成。
Org Lett. 2012 Mar 16;14(6):1576-9. doi: 10.1021/ol300310e. Epub 2012 Mar 8.
6
Biological synthesis of quercetin 3-O-N-acetylglucosamine conjugate using engineered Escherichia coli expressing UGT78D2.利用表达 UGT78D2 的工程大肠杆菌生物合成槲皮素 3-O-N-乙酰氨基葡萄糖苷缀合物。
Appl Microbiol Biotechnol. 2012 Mar;93(6):2447-53. doi: 10.1007/s00253-011-3747-8. Epub 2011 Dec 13.
7
Fluorescence light-up recognition of DNA nucleotide based on selective abasic site binding of an excited-state intramolecular proton transfer probe.基于激发态分子内质子转移探针对碱基切除修复中无碱基位点的选择性识别实现 DNA 核苷酸的光致荧光增强。
Analyst. 2011 Nov 7;136(21):4480-5. doi: 10.1039/c1an15652g. Epub 2011 Sep 22.
8
Flavonols: old compounds for old roles.类黄酮：古老的化合物，古老的角色。
Ann Bot. 2011 Nov;108(7):1225-33. doi: 10.1093/aob/mcr234. Epub 2011 Aug 31.
9
Quercetin. Monograph.槲皮素。专论。
Altern Med Rev. 2011 Jun;16(2):172-94.
10
Flavonoids: potential Wnt/beta-catenin signaling modulators in cancer.类黄酮：癌症中潜在的 Wnt/β-连环蛋白信号通路调节剂。
Life Sci. 2011 Oct 10;89(15-16):545-54. doi: 10.1016/j.lfs.2011.05.003. Epub 2011 May 18.
Zotero 插件