杯[4]芳烃α-氨基膦酸：碱性磷酸酶的不对称合成及对映选择性抑制
Calix[4]arene alpha-aminophosphonic acids: asymmetric synthesis and enantioselective inhibition of an alkaline phosphatase.
作者信息
Cherenok Sergiy, Vovk Andriy, Muravyova Iryna, Shivanyuk Alexander, Kukhar Valery, Lipkowski Janusz, Kalchenko Vitaly
机构信息
The Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska, 5, 02094, Kyiv-94, Ukraine.
出版信息
Org Lett. 2006 Feb 16;8(4):549-52. doi: 10.1021/ol052469a.
[structure: see text] Chiral calix[4]arene alpha-aminophosphonic acids were obtained through diastereoselective Pudovik-type addition of sodium ethyl phosphites to the chiral calixarene imines, removal of chiral auxiliary groups, and mild dealkylation of phosphonate fragments. The diacids obtained show inhibitory activity toward porcine kidney alkaline phosphatase that depends considerably on the absolute configuration of the alpha-carbon atoms.
[结构：见正文] 通过亚磷酸乙酯对手性杯芳烃亚胺进行非对映选择性的普多维克型加成反应、去除手性辅助基团以及膦酸酯片段的温和脱烷基化反应，制得了手性杯[4]芳烃α-氨基膦酸。所得到的二酸对猪肾碱性磷酸酶表现出抑制活性，该活性在很大程度上取决于α-碳原子的绝对构型。
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