Chawla S, Mutenda E K, Dixon H B, Freeman S, Smith A W
Department of Biochemistry, University of Cambridge, U.K.
Biochem J. 1995 Jun 15;308 ( Pt 3)(Pt 3):931-5. doi: 10.1042/bj3080931.
3-Arsonopyruvate was prepared in four steps from glycine. The arsenic-carbon bond was formed by a Meyer reaction between alkaline arsenite and 2-bromo-3-hydroxy-2-(hydroxymethyl)propionic acid; the 3-arsono-2-hydroxy-2-(hydroxymethyl) propionic acid formed was oxidized with periodate to give 3-arsonopyruvate. This proves to be an alternative substrate for phosphoenolpyruvate mutase, giving pyruvate, which was assayed using lactate dehydrogenase. The K(m) is 20 microM, similar to that observed for the natural substrate phosphonopyruvate (17 microM), whereas the kcat. of 0.01 s-1 was much lower than that for phosphonopyruvate (58 s-1). Arsonopyruvate competitively inhibited the action of the mutase on phosphonopyruvate.
3-胂丙酮酸由甘氨酸经四个步骤制备而成。通过碱性亚砷酸盐与2-溴-3-羟基-2-(羟甲基)丙酸之间的迈耶反应形成砷-碳键；生成的3-胂基-2-羟基-2-(羟甲基)丙酸用过碘酸盐氧化得到3-胂丙酮酸。事实证明，这是磷酸烯醇丙酮酸变位酶的一种替代底物，可生成丙酮酸，使用乳酸脱氢酶对其进行测定。其米氏常数（K(m)）为20微摩尔，与天然底物膦丙酮酸（17微摩尔）的观测值相似，而其催化常数（kcat.）为0.01秒⁻¹，远低于膦丙酮酸的（58秒⁻¹）。胂丙酮酸竞争性抑制变位酶对膦丙酮酸的作用。
