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.
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页码：376 / 381
页数：6
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