一些环磷酸腺苷烷基三酯的合成与性质
Synthesis and properties of some cyclic AMP alkyl phosphotriesters.
作者信息
Gohil R N, Gillen R G, Nagyvary J
出版信息
Nucleic Acids Res. 1974 Dec;1(12):1691-701. doi: 10.1093/nar/1.12.1691.
Abstract
Cyclic AMP was converted to its phosphotriesters according to the classical approach of phosphate activation with a sulfonyl chloride, followed by esterification with an alcohol. The methyl, ethyl, propyl, butyl and cetyl triesters were prepared, and some of their physical-chemical properties determined. Alkaline hydrolysis of these alkyl phosphotriesters resulted predominantly in ring opening. On the other hand, nucleophilic attack by thiourea led to the formation of cAMP as the main product. The conclusion can be drawn from these results that cAMP phosphotriesters could serve as suitable storage forms of cAMP, and cyclic triesters may be the best vehicle of transporting nucleotides through biological membranes.
摘要
根据用磺酰氯活化磷酸的经典方法，将环磷酸腺苷（cAMP）转化为其磷酸三酯，然后用醇进行酯化反应。制备了甲基、乙基、丙基、丁基和十六烷基三酯，并测定了它们的一些物理化学性质。这些烷基磷酸三酯的碱性水解主要导致开环。另一方面，硫脲的亲核进攻导致以cAMP作为主要产物生成。从这些结果可以得出结论，cAMP磷酸三酯可以作为cAMP合适的储存形式，并且环状三酯可能是通过生物膜运输核苷酸的最佳载体。
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