Novel synthesis of [33P]-(2-chloroethyl)phosphonic acid.
Novel synthesis of [33P]-(2-chloroethyl)phosphonic acid.
复制标题
[33P]-(2-氯乙基)膦酸的新合成。
DOI：
10.1021/jo0013608
复制
发表时间：
2001
期刊：
影响因子：
--
通讯作者：
Casida,JE
中科院分区：
文献类型：
--
作者：
Zhang,N;Casida,JE
膦酸及其衍生物在生物过程的调节中起着重要作用。1它们被广泛用作药物和农用化学品，例如，草甘膦[N-（膦酰基甲基）甘氨酸]作为除草剂，乙烯利[（2-氯乙基）膦酸]作为植物生长调节剂。2它们的安全和有效使用需要彻底了解它们的代谢命运和毒理学。例如，乙烯利抑制哺乳动物（包括人类）的血浆丁酰胆碱酯酶，可能是通过磷酸化活性位点的丝氨酸残基。[33 P]-乙烯利的放射合成的挑战在于从最容易获得的前体[33 P]-磷酸（H3 PO 4）开始形成磷-碳键。此外，乙烯利的酸性及其在中性和碱性条件下的不稳定性4需要清洁有效的程序来最大限度地减少纯化。32 P-和33 P-的早期多步合成
Phosphonic acids and their derivatives play an important role in the regulation of biological processes. 1 They are widely used as pharmaceuticals and agrochemicals, eg, glyphosate [N-(phosphonomethyl) glycine] as a herbicide and ethephon [(2-chloroethyl) phosphonic acid] as a plant growth regulator. 2 Their safe and effective use requires a thorough understanding of their metabolic fate and toxicology. For example, ethephon inhibits plasma butyrylcholinesterase in mammals including humans, presumably by phosphorylation of a serine residue at the active site. 3 Further study of the mechanism and consequences of this enzyme inhibition and possible phosphorylation of other proteins required the radiosynthesis of [33P]-ethephon.The challenge for radiosynthesis of ethephon lies in formation of the phosphorus-carbon bond starting from the most readily available precursor,[33P]-phosphoric acid (H3PO4). In addition, the acid nature of ethephon as well as its instability under neutral and basic conditions4 require a clean and efficient procedure to minimize purification. Earlier multistep syntheses of 32P-and 33P-