Synthesis of cardiolipin derivatives with protection of the free hydroxyl: its application to the study of cardiolipin stimulation of cytochrome c oxidase.
Synthesis of cardiolipin derivatives with protection of the free hydroxyl: its application to the study of cardiolipin stimulation of cytochrome c oxidase.
复制标题
保护游离羟基的心磷脂衍生物的合成：其在心磷脂刺激细胞色素c氧化酶的研究中的应用。
DOI：
10.1021/bi00421a042
复制
发表时间：
1988
期刊：
影响因子：
2.9
通讯作者：
Robinson,NC
中科院分区：
文献类型：
--
作者：
Dale,MP;Robinson,NC
1988年6月29日接收的修订版摘要：合成了保留极性头基上的游离羟基的心磷脂衍生物。使用四氢吡喃基乙二胺保护该羟基，在心磷脂（CL）的两个2-位上进行脂肪酰基取代。以高产率获得了二取代的衍生物。脱脂细胞色素c氧化酶活性的刺激显示出对这些CL衍生物的浓度的双曲线依赖性。两个活化参数，表观解离常数（Xd，app）和分子活性的最大变化（Δ Act），取决于尾部的链长，对饱和度的依赖性较小。天然CL（92% C18：2，8% C18：1）和油酸二取代CL（47% C18：2，52% C18：]）在刺激细胞色素c氧化酶活性方面同样有效，在0.3% Triton X-100中孵育并在月桂基麦芽糖苷中测定时，表观解离常数约为1 µ。然而，用己酸二取代的CL是一种较差的活化剂，表观解离常数为6.8 µ，AActmax为天然CL的50%。完全去除两个脂肪酸尾的二溶血心磷脂对细胞色素c氧化酶活性的刺激可以忽略不计。
Revised Manuscript Received June 29, 1988 abstract: Cardiolipin derivatives retaining the free hydroxyl on the polar head group were synthesized. With the use of a tetrahydropyranyl etherto protect this hydroxyl, fatty acyl substitutions were made at both of the 2-positions of cardiolipin (CL). The disubstituted derivatives were obtained in high yields. The stimulation of delipidated cytochrome c oxidase activity shows a hyperbolic dependence on the concentration of these CL derivatives. Both activation parameters, the apparent dissociation constant (Xd, app) and the maximum change in molecular activity (AAct^), depend on the chain length of the tails, with less dependence on the degree of saturation. Natural CL (92% C18: 2, 8% C18: 1) and CL disubstituted with oleic acid (47% C18: 2, 52% C18:]) were equally effective at stimulating cytochrome c oxidase activity, with an apparent dissociation constant of approximately 1 µ when incubated in 0.3% Triton X-100 and assayed in lauryl maltoside. CL disubstituted with hexanoic acid, however, is a poorer activator, with an apparent dissociation constant of 6.8 µ and a AActmax that is 50% of that achieved with natural CL. Dilysocardiolipin, with complete removal of two of the fatty acid tails, shows negligible stimulationof cytochrome c oxidase activity.