ADP-ribosylation of elongation factor 2 by diphtheria toxin. NMR spectra and proposed structures of ribosyl-diphthamide and its hydrolysis products.
ADP-ribosylation of elongation factor 2 by diphtheria toxin. NMR spectra and proposed structures of ribosyl-diphthamide and its hydrolysis products.
复制标题
DOI：
10.1016/s0021-9258(19)70365-2
复制
发表时间：
1980-11
期刊：
影响因子：
--
通讯作者：
B. Ness;J. Howard;James W. Bo y
中科院分区：
文献类型：
--
作者：
B. Ness;J. Howard;James W. Bo y
经白喉毒素二磷酸腺苷核糖化修饰的延伸因子2中的新氨基酸二苯乙胺的核磁共振波谱分析表明，它是2-[3-carboxyamido-3-(trimethylammonio)propyl]histidine.。以ADP-核糖延伸因子2为原料，经酶解制备核糖基二苯酰胺，再经化学水解制得三个化合物(Van Ness，B.G.，Howard，J.B.和Bodley，J.W.(1980)J.Biol)。化学。255、10717-10720)。联苯乙胺2H2O中的质子核磁共振波谱表明，组氨酸的元素减去碳2质子加上14个额外的不可交换质子。这些质子被归因于咪唑环上碳2的广泛修饰。核糖基二苯胺在2H2O中的质子核磁共振谱显示，只有在二氢呋喃中看到的质子加上那些预期的呋喃核糖基团。组氨酸衍生的质子以及修饰侧链的几个质子的化学位移与pH有关。核糖基二苯酰胺的天然丰度碳13核磁共振谱也表明组氨酸和核糖加7个额外的碳原子属于咪唑环的修饰。根据核糖基二苯胺异构体质子的核磁共振波谱性质，我们推测该核糖与组氨酸咪唑环上的一个氮基相连。
NMR spectral analysis of the novel amino acid, diphthamide, in elongation factor 2 which is ADP-ribosylated by diphtheria toxin suggests that it is 2-[3-carboxyamido-3-(trimethylammonio)propyl]histidine. Ribosyl-diphthamide was prepared by enzymatic hydrolysis of ADP-ribosyl-elongation factor 2 and three compounds were produced by its chemical hydrolysis (Van Ness, B. G., Howard, J. B., and Bodley, J. W. (1980) J. Biol. Chem. 255, 10717-10720). Proton NMR spectroscopy in 2H2O of diphthine demonstrated the elements of histidine minus the carbon 2 proton plus 14 additional nonexchangeable protons. These protons were attributed to an extensive modification at carbon 2 of the imidazole ring. Proton NMR spectroscopy in 2H2O of ribosyl-diphthamide showed only those protons seen in diphthine plus those expected of a ribofuranosylmoiety. Chemical shift dependence on pH was demonstrated for the histidine-derived protons as well as several protons of the modifying side chain. Natural abundance carbon 13 NMR spectroscopy of ribosyldiphthamide also showed the elements of histidine and ribose plus 7 additional carbon atoms attributed to the modification of the imidazole ring. Based on the NMR spectral properties of the anomeric proton of ribosyldiphthamide we propose that the ribose is linked to one of the nitrogens of the histidine imidazole ring.