The synthesis of an acyclic nucleotide analogue, (E)-9-(3-phosphonylmethoxypropen-1-yl)adenine

被引：0
|
作者：
Ivanov, AV [1 ]
Jasko, MV [1 ]
Skoblov, YS [1 ]
Kukhanova, MK [1 ]
机构：
[1] Russian Acad Sci, VA Engelhardt Mol Biol Inst, Moscow 119991, Russia
来源：
CHEMISTRY OF NUCLEIC ACID COMPONENTS | 2002年 / 5卷
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D O I：
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中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
(E)-9-(3-Hydroxypropen-1-yl)adenine was obtained by alkylation of adenine with 1,2-di-O-mesyl-3-O-tritylglycerol followed by elimination of mesyl group and detritylation. Cis/trans selectivity of the reaction was investigated. The resulting hydroxypropenyladenine was alkylated by ethyl iodomethylphosphonate in the presence of NaH, and treated with brom otrimethylsilane to give the target (E)-9-(3-phosphonomethoxypropen-1-yl) adenine. It was converted to the corresponding phosphonate diphosphate by reaction with bis(tributylammonium) pyrophosphate in the presence of 1,1'-carbonyldiimidazole. The substrate properties of the phosphonate towards human adenylate kinase were demonstrated.
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页码：43 / 47
页数：5
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