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(5'S)-8,5'-cyclo-2'-deoxyguanosine is a strong block to replication, a potent pol V-dependent mutagenic lesion, and is inefficiently repaired in Escherichia coli.(5'S)-8,5'-环-2'-脱氧鸟苷是一种强烈的复制阻断物、一种有效的依赖于聚合酶 V 的诱变损伤物，并且在大肠杆菌中修复效率较低。
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Measurement of (5'R)- and (5'S)-8,5'-cyclo-2'-deoxyadenosines in DNA in vivo by liquid chromatography/isotope-dilution tandem mass spectrometry.采用液相色谱/同位素稀释串联质谱法对体内DNA中的(5'R)-和(5'S)-8,5'-环-2'-脱氧腺苷进行测定。
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Accumulation of (5'S)-8,5'-cyclo-2'-deoxyadenosine in organs of Cockayne syndrome complementation group B gene knockout mice.（5'S）-8,5'-环-2'-脱氧腺苷在科凯恩综合征互补组B基因敲除小鼠器官中的蓄积。
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The 8,5'-cyclopurine-2'-deoxynucleosides: candidate neurodegenerative DNA lesions in xeroderma pigmentosum, and unique probes of transcription and nucleotide excision repair.8,5'-环嘌呤-2'-脱氧核苷：着色性干皮病中潜在的神经退行性DNA损伤，以及转录和核苷酸切除修复的独特探针。
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[1,3, NH2-(15)N3] (5'S)-8,5'-环-2'-脱氧鸟苷的合成

Synthesis of [1,3, NH2-(15)N3] (5'S)-8,5'-cyclo-2'-deoxyguanosine.

作者信息

Malik Chanchal K, Das Rajat S, Basu Ashis K

机构信息

Department of Chemistry, University of Connecticut, Storrs, CT, 06269, USA.

出版信息

J Labelled Comp Radiopharm. 2013 Jun 30;56(8):376-81. doi: 10.1002/jlcr.3051. Epub 2013 May 23.

DOI:10.1002/jlcr.3051
PMID:24285476
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5382719/
Abstract

To facilitate NMR studies and low-level detection in biological samples by mass spectrometry, [1,3, NH2-(15)N3] (5'S)-8,5'-cyclo-2'-deoxyguanosine was synthesized from imidazole-4,5-dicarboxylic acid in 21 steps. The three (15)N isotopes were introduced during the chemo-enzymatic preparation of [1,3, NH2-(15)N3]-2'-deoxyguanosine using an established procedure. The (15)N-labeled 2'-deoxyguanosine was converted to a 5'-phenylthio derivative, which allowed the 8-5' covalent bond formation via photochemical homolytic cleavage of the C-SPh bond. SeO2 oxidation of C-5' followed by sodium borohydride reduction and deprotection gave the desired product in good yield. The isotopic purity of the [1,3, NH2-(15)N3] (5'S)-8,5'-cyclo-2'-deoxyguanosine was in excess of 99.94 atom% based on liquid chromatography-mass spectrometry measurements.

摘要

为便于通过质谱对生物样品进行核磁共振研究和低水平检测，1,3,NH₂-(¹⁵)N₃-8,5'-环-2'-脱氧鸟苷由咪唑-4,5-二羧酸经21步合成。在使用既定程序对[1,3,NH₂-(¹⁵)N₃]-2'-脱氧鸟苷进行化学酶法制备过程中引入了三种(¹⁵)N同位素。将(¹⁵)N标记的2'-脱氧鸟苷转化为5'-苯硫基衍生物，这使得通过C-SPh键的光化学均裂裂解形成8-5'共价键成为可能。C-5'经二氧化硒氧化，随后用硼氢化钠还原和脱保护，以良好的产率得到了所需产物。基于液相色谱-质谱测量，1,3,NH₂-(¹⁵)N₃-8,5'-环-2'-脱氧鸟苷的同位素纯度超过99.94原子%。