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

被引：0

作者：

Malik, Chanchal K. ^{[1
]}

Das, Rajat S. ^{[1
]}

Basu, Ashis K. ^{[1
]}

机构：

[1] Univ Connecticut, Dept Chem, Storrs, CT 06269 USA

来源：

JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS | 2013年 / 56卷 / 08期

关键词：

cyclo-dG; -radiation damage; tandem DNA lesion; N-15-S-cdG; NUCLEOTIDE EXCISION-REPAIR; DNA LESIONS; 8,5'-CYCLOPURINE-2'-DEOXYNUCLEOSIDES; SPECTROMETRY; NUCLEOSIDES;

D O I：

10.1002/jlcr.3051

中图分类号：

Q5 [生物化学];

学科分类号：

071010 ; 081704 ;

摘要：

To facilitate NMR studies and low-level detection in biological samples by mass spectrometry, [1,3,NH2-N-15(3)] (5S)-8,5-cyclo-2-deoxyguanosine was synthesized from imidazole-4,5-dicarboxylic acid in 21 steps. N-15 isotopes were introduced during the chemo-enzymatic preparation of [1,3, NH2-N-15(3)]-2-deoxyguanosine using an established procedure. N-15-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. (2)-N-15(3)] (5S)-8,5-cyclo-2-deoxyguanosine was in excess of 99.94 atom% based on liquid chromatography-mass spectrometry measurements. Copyright (c) 2013 John Wiley & Sons, Ltd.

引用

页码：376 / 381

页数：6

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