电子圆二色光谱的计算研究预测了鸟嘌呤氧化产物5-羧酰胺基-5-甲酰胺基-2-亚氨基乙内酰脲的绝对构型归属。
Computational studies of electronic circular dichroism spectra predict absolute configuration assignments for the guanine oxidation product 5-carboxamido-5-formamido-2-iminohydantoin.
作者信息
Fleming Aaron M, Alshykhly Omar, Orendt Anita M, Burrows Cynthia J
机构信息
Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, Utah 84112-0850, USA.
Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, Utah 84112-0850, USA ; Center for High Performance Computing, University of Utah, Salt Lake City, Utah 84112-0190, USA.
出版信息
Tetrahedron Lett. 2015 Jun 3;56(23):3191-3196. doi: 10.1016/j.tetlet.2014.12.052.
Abstract
Oxidation of the guanine heterocycle by two electrons can yield the chiral product 5-carboxamido-5-formamido-2-iminohydantoin (). The free base enantiomers were synthesized from 2'-deoxyguanosine oxidized with a Cu(II)/HO oxidant system followed by hydrolysis of the -glycosidic bond. These isomers were each studied by electronic circular dichroism spectroscopy for determination of their absolute configurations. Time-dependent density functional theory calculations of the expected spectra were completed in both the gas phase and with solvent modeling in order to interpret the experimental spectra and provide the absolute configuration assignments.
摘要
鸟嘌呤杂环经双电子氧化可生成手性产物5-羧酰胺基-5-甲酰胺基-2-亚氨基乙内酰脲（）。游离碱对映体由2'-脱氧鸟苷经Cu(II)/HO氧化体系氧化，随后糖苷键水解合成。通过电子圆二色光谱对这些异构体进行了研究，以确定它们的绝对构型。在气相和溶剂模拟条件下完成了预期光谱的含时密度泛函理论计算，以便解释实验光谱并给出绝对构型归属。
相似文献
1
Computational studies of electronic circular dichroism spectra predict absolute configuration assignments for the guanine oxidation product 5-carboxamido-5-formamido-2-iminohydantoin.电子圆二色光谱的计算研究预测了鸟嘌呤氧化产物5-羧酰胺基-5-甲酰胺基-2-亚氨基乙内酰脲的绝对构型归属。
Tetrahedron Lett. 2015 Jun 3;56(23):3191-3196. doi: 10.1016/j.tetlet.2014.12.052.
2
Guanine oxidation product 5-carboxamido-5-formamido-2-iminohydantoin induces mutations when bypassed by DNA polymerases and is a substrate for base excision repair.鸟嘌呤氧化产物5-羧酰胺基-5-甲酰胺基-2-亚氨基乙内酰脲在被DNA聚合酶绕过复制时会诱导突变，并且是碱基切除修复的底物。
Chem Res Toxicol. 2015 Sep 21;28(9):1861-71. doi: 10.1021/acs.chemrestox.5b00302. Epub 2015 Sep 2.
3
Insights into the 5-Carboxamido-5-Formamido-2-Iminohydantoin Structural Isomerization Equilibria.5-羧基氨甲酰基-5-甲酰胺基-2-亚氨基海因结构异构平衡的深入研究。
J Org Chem. 2022 Sep 2;87(17):11865-11870. doi: 10.1021/acs.joc.2c01371. Epub 2022 Aug 12.
4
Computational Study of the Oxidation of Guanine To Form 5-Carboxyamido-5-formamido-2-iminohydantoin (2Ih).鸟嘌呤氧化生成 5-羧基氨基-5-甲酰胺基-2-亚氨基海因（2Ih）的计算研究。
Chem Res Toxicol. 2019 Nov 18;32(11):2295-2304. doi: 10.1021/acs.chemrestox.9b00304. Epub 2019 Oct 15.
5
Reconciliation of chemical, enzymatic, spectroscopic and computational data to assign the absolute configuration of the DNA base lesion spiroiminodihydantoin.综合化学、酶学、光谱学和计算数据，确定 DNA 碱基损伤螺环亚氨基二氢嘧啶的绝对构型。
J Am Chem Soc. 2013 Dec 4;135(48):18191-204. doi: 10.1021/ja409254z. Epub 2013 Nov 21.
6
Identification of the Major Product of Guanine Oxidation in DNA by Ozone.臭氧氧化鸟嘌呤在 DNA 中生成的主要产物的鉴定。
Chem Res Toxicol. 2022 Oct 17;35(10):1809-1813. doi: 10.1021/acs.chemrestox.2c00103. Epub 2022 Jun 1.
7
The 2Ih and G Proximity Consequences on Charge Transfer through -DNA: Theoretical Studies of Clustered DNA Damage.通过 -DNA 进行电荷转移的 2Ih 和 G 接近后果：聚集 DNA 损伤的理论研究。
Molecules. 2023 Feb 26;28(5):2180. doi: 10.3390/molecules28052180.
8
Determination of the absolute configurations of bicyclo[3.1.0]hexane derivatives via electronic circular dichroism, optical rotation dispersion and vibrational circular dichroism spectroscopy and density functional theory calculations.通过电子圆二色性、旋光色散和振动圆二色性光谱以及密度泛函理论计算，确定双环[3.1.0]己烷衍生物的绝对构型。
Org Biomol Chem. 2010 Aug 21;8(16):3777-83. doi: 10.1039/c002655g. Epub 2010 Jun 22.
9
A 2-iminohydantoin from the oxidation of guanine.鸟嘌呤氧化产生的一种2-亚氨基乙内酰脲。
Chem Res Toxicol. 2006 Apr;19(4):506-10. doi: 10.1021/tx0600144.
10
Absolute configurations of spiroiminodihydantoin and allantoin stereoisomers: comparison of computed and measured electronic circular dichroism spectra.螺环亚氨基二氢尿嘧啶和尿囊素立体异构体的绝对构型：计算电子圆二色光谱与实测电子圆二色光谱的比较
Chem Res Toxicol. 2009 Jun;22(6):1189-93. doi: 10.1021/tx900107q.
引用本文的文献
1
Excision of Oxidatively Generated Guanine Lesions by Competitive DNA Repair Pathways.竞争性 DNA 修复途径切除氧化生成的鸟嘌呤损伤。
Int J Mol Sci. 2021 Mar 7;22(5):2698. doi: 10.3390/ijms22052698.
2
Interrogation of Base Pairing of the Spiroiminodihydantoin Diastereomers Using the α-Hemolysin Latch.利用α-溶血素锁扣对螺旋咪唑二氢乙内酰脲非对映异构体的碱基配对进行研究。
Biochemistry. 2017 Mar 21;56(11):1596-1603. doi: 10.1021/acs.biochem.6b01175. Epub 2017 Mar 9.
3
Formation and processing of DNA damage substrates for the hNEIL enzymes.人NEIL酶的DNA损伤底物的形成与加工
Free Radic Biol Med. 2017 Jun;107:35-52. doi: 10.1016/j.freeradbiomed.2016.11.030. Epub 2016 Nov 20.
4
Guanine oxidation product 5-carboxamido-5-formamido-2-iminohydantoin induces mutations when bypassed by DNA polymerases and is a substrate for base excision repair.鸟嘌呤氧化产物5-羧酰胺基-5-甲酰胺基-2-亚氨基乙内酰脲在被DNA聚合酶绕过复制时会诱导突变，并且是碱基切除修复的底物。
Chem Res Toxicol. 2015 Sep 21;28(9):1861-71. doi: 10.1021/acs.chemrestox.5b00302. Epub 2015 Sep 2.
5
5-Carboxamido-5-formamido-2-iminohydantoin, in Addition to 8-oxo-7,8-Dihydroguanine, Is the Major Product of the Iron-Fenton or X-ray Radiation-Induced Oxidation of Guanine under Aerobic Reducing Conditions in Nucleoside and DNA Contexts.5-羧酰胺基-5-甲酰胺基-2-亚氨基乙内酰脲，除8-氧代-7,8-二氢鸟嘌呤外，是核苷和DNA环境中在有氧还原条件下铁-芬顿反应或X射线辐射诱导鸟嘌呤氧化的主要产物。
J Org Chem. 2015 Jul 17;80(14):6996-7007. doi: 10.1021/acs.joc.5b00689. Epub 2015 Jul 1.
6
Rates of chemical cleavage of DNA and RNA oligomers containing guanine oxidation products.含鸟嘌呤氧化产物的DNA和RNA寡聚物的化学裂解速率。
Chem Res Toxicol. 2015 Jun 15;28(6):1292-300. doi: 10.1021/acs.chemrestox.5b00096. Epub 2015 Apr 22.
本文引用的文献
1
Crystal structure of DNA polymerase β with DNA containing the base lesion spiroiminodihydantoin in a templating position.DNA聚合酶β与在模板位置含有碱基损伤螺环亚氨基二氢尿嘧啶的DNA的晶体结构。
Biochemistry. 2014 Apr 8;53(13):2075-7. doi: 10.1021/bi500270e. Epub 2014 Mar 26.
2
One-electron oxidation reactions of purine and pyrimidine bases in cellular DNA.嘌呤和嘧啶碱基在细胞 DNA 中的单电子氧化反应。
Int J Radiat Biol. 2014 Jun;90(6):423-32. doi: 10.3109/09553002.2013.877176. Epub 2014 Apr 3.
3
Reconciliation of chemical, enzymatic, spectroscopic and computational data to assign the absolute configuration of the DNA base lesion spiroiminodihydantoin.综合化学、酶学、光谱学和计算数据，确定 DNA 碱基损伤螺环亚氨基二氢嘧啶的绝对构型。
J Am Chem Soc. 2013 Dec 4;135(48):18191-204. doi: 10.1021/ja409254z. Epub 2013 Nov 21.
4
Thermodynamic profiles and nuclear magnetic resonance studies of oligonucleotide duplexes containing single diastereomeric spiroiminodihydantoin lesions.含有单非对映异构螺环亚氨基二氢嘧啶核苷损伤的寡核苷酸双链的热力学谱和核磁共振研究。
Biochemistry. 2013 Feb 26;52(8):1354-63. doi: 10.1021/bi301566v. Epub 2013 Feb 13.
5
A single nuclease-resistant linkage in DNA as a versatile tool for the characterization of DNA lesions: application to the guanine oxidative lesion "G+34" generated by metalloporphyrin/KHSO(5) reagent.DNA 中单链核酸酶抗性连接作为一种用于 DNA 损伤特征分析的多功能工具：应用于金属卟啉/KHSO(5)试剂产生的鸟嘌呤氧化损伤“G+34”。
Chem Res Toxicol. 2012 Nov 19;25(11):2505-12. doi: 10.1021/tx300319y. Epub 2012 Oct 12.
6
Lead(II)-catalyzed oxidation of guanine in solution studied with electrospray ionization mass spectrometry.电喷雾电离质谱法研究溶液中 II 价铅催化的鸟嘌呤氧化。
J Phys Chem B. 2012 Oct 4;116(39):11791-7. doi: 10.1021/jp302720z. Epub 2012 Sep 20.
7
Lifetimes and reaction pathways of guanine radical cations and neutral guanine radicals in an oligonucleotide in aqueous solutions.寡核苷酸在水溶液中鸟嘌呤自由基阳离子和中性鸟嘌呤自由基的寿命和反应途径。
J Am Chem Soc. 2012 Mar 14;134(10):4955-62. doi: 10.1021/ja212186w. Epub 2012 Feb 29.
8
Chemical and biological consequences of oxidatively damaged guanine in DNA.DNA 中氧化损伤鸟嘌呤的化学和生物学后果。
Free Radic Res. 2012 Apr;46(4):420-41. doi: 10.3109/10715762.2011.653968. Epub 2012 Feb 22.
9
Absolute stereochemistry and preferred conformations of urate degradation intermediates from computed and experimental circular dichroism spectra.尿酸降解中间体的计算和实验圆二色光谱的绝对立体化学和优势构象。
Org Biomol Chem. 2011 Jul 21;9(14):5149-55. doi: 10.1039/c1ob05433c. Epub 2011 Jun 7.
10
Comparison of Transition Metal-Mediated Oxidation Reactions of Guanine in Nucleoside and Single-Stranded Oligodeoxynucleotide Contexts.核苷和单链寡脱氧核苷酸环境中鸟嘌呤的过渡金属介导氧化反应的比较
Inorganica Chim Acta. 2011 Apr 15;369(1):240-246. doi: 10.1016/j.ica.2010.12.063.
Zotero 插件