Reactive phosphonic acids as prebiotic carriers of phosphorus
Reactive phosphonic acids as prebiotic carriers of phosphorus
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DOI：
10.1007/pl00006140
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发表时间：
1997-03-01
影响因子：
3.9
通讯作者：
Schwartz, AW
中科院分区：
文献类型：
--
作者：
DeGraaf, RM;Visscher, J;Schwartz, AW
膦酸是在默奇森陨石中检测到的唯一含磷有机化合物。我们先前描述了使用亚磷酸钠作为亚磷酸根的来源来合成甲基膦酸、羟甲基膦酸和1-羟乙基膦酸。我们现在表明，在亚磷酸钠存在下，乙炔的稀水溶液的紫外线照射导致乙烯基膦酸的合成。在中性至碱性pH下，乙烯基膦酸在光化学条件下反应以产生膦酰基乙醛和2-羟乙基膦酸作为主要产物，以及较低产率的1-羟乙基膦酸、膦酰基乙酸和乙基膦酸。在这些产物中，膦酰基乙醛作为益生元碳水化合物衍生物的潜在前体特别令人感兴趣。
Phosphonic acids are the only phosphorus-containing organic compounds detected in the Murchison meteorite. We earlier described the synthesis of methyl-, hydroxymethyl-, and 1-hydroxyethyl phosphonic acids using sodium phosphite as a source of phosphite radicals. We now show that ultraviolet irradiation of dilute aqueous solutions of acetylene in the presence of sodium phosphite leads to the synthesis of vinyl phosphonic acid. At neutral to basic pH, vinyl phosphonic acid reacts under photochemical conditions to produce phosphonoacetaldehyde and 2-hydroxyethyl phosphonic acid as the major products, as well as smaller yields of l-hydroxyethyl phosphonic acid, phosphonoacetic acid, and ethyl phosphonic acid. Of these products, phosphonoacetaldehyde is particularly interesting as a potential precursor of prebiotic carbohydrate derivatives.