9-(2-Deoxy-ß-D-xylofuranosyl)adenine and 1-(2-Deoxy-ß-D-xylofuranosyl)thymine: Phosphorylation and Stability
9-(2-Deoxy-ß-D-xylofuranosyl)adenine and 1-(2-Deoxy-ß-D-xylofuranosyl)thymine: Phosphorylation and Stability
复制标题
9-(2-脱氧-ß-D-呋喃木糖基)腺嘌呤和 1-(2-脱氧-ß-D-呋喃木糖基)胸腺嘧啶：磷酸化和稳定性
DOI：
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发表时间：
1992
期刊：
影响因子：
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通讯作者：
F. Seela
中科院分区：
文献类型：
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作者：
M. Krečmerová;F. Seela
1-（2-脱氧-β-D-呋喃木糖基）胸腺嘧啶（1）或9-（2-脱氧-β-D-呋喃木糖基）腺嘌呤（3）与磷酰氯发生磷酸化反应，得到环状3′，5 ′-磷酸（2和4a），而不是5′-单磷酸（8a或8b）。后者是通过3′-O-苯甲酰化2′-脱氧-β-D-木糖苷（7 a，B）的磷酸化和随后的苯甲酰基的碱催化去除获得的。作为母体dA的化合物3在酸性介质中脱嘌呤，该反应在N6-苯甲酰基衍生物9 b的情况下得到促进，并且在引入脒保护基后被还原。与2 ′-脱氧-β-D-呋喃核糖核苷相比，2′-脱氧-β-D-呋喃木糖核苷的N-糖基键水解增强两倍。
Abstract Phosphorylation of 1-(2-deoxy-β-D-xylofuranosyl)thymine (1) or 9-(2-deoxy-β-D-xylofuranosyl)adenine (3) with phosphoryl chloride gives the cyclic 3′,5′-phosphates (2 and 4a) but not the 5′-monophosphates 8a or 8b. The latter are obtained by phosphorylation of the 3′-0-benzoylated 2′-deoxy-β-D-xylonucleosides (7a, b) and subsequent base-catalyzed removal of the benzoyl groups. Compound 3, as the parent dA, depurinates in acidic medium, a reaction which is facilitated in the case of the N6-benzoyl derivative 9b and reduced after the introduction of an amidine protecting group. N-Glycosylic bond hydrolysis of 2′-deoxy-β-D-xylofuranosyl nucleosides is enhanced by a factor of two compared to 2′-deoxy-β-D-ribofuranosyl nucleosides.