phosphoribosyl ATP | 1110-99-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷酸
• 英文名称: phosphoribosyl ATP
• 英文别名: PR-ATP；phosphoribosyl-ATP；[[(2R,3S,4R,5R)-5-[1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(phosphonooxymethyl)oxolan-2-yl]-6-iminopurin-9-yl]-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate
• CAS: 1110-99-2
• 化学式: C₁₅H₂₅N₅O₂₀P₄
• 分子量: 719.28
• InChiKey: RKNHJBVBFHDXGR-KEOHHSTQSA-N

物化性质

• 沸点：
  1191.0±75.0 °C(Predicted)
• 密度：
  2.66±0.1 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  -8.9
• 重原子数：
  44
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  383
• 氢给体数：
  11
• 氢受体数：
  23

反应信息

• 作为反应物：
  描述：

  phosphoribosyl ATP 在 HEPES buffer 、 potassium tert-butylate 、 水 、 magnesium chloride 作用下， 以 二甲基亚砜 、 乙腈 为溶剂， 反应 53.0h， 生成 phosphoribosyl-AMP
  参考文献：
  名称：

  Cyclic ADP-Ribose: Synthesis and Structural Assignment

  摘要：

  Cyclic ADP-ribose (cADPR) is a naturally occurring cyclic nucleotide and a potent mediator of calcium mobilization in many mammalian tissues. Previous studies have shown that cADPR is synthesized from beta-NAD(+) via the scission of the nicotinamide-ribose linkage and cyclization by forming a new bond between the ribose and the nitrogen of the adenine ring. However, the position and stereochemistry of this newly formed linkage were not unequivocally determined. In this study we have established that cADPR has the anomeric carbon of the ribose attached onto the N-1-nitrogen of the adenine nucleus via a beta-N-glycosyl linkage. The structural assignment was made by correlating cADPR to N-1-(5'-phosphoribosyl)AMP, a known intermediate of histidine biosynthesis. This was achieved by cleaving the pyrophosphate bond of cADPR under conditions (DMSO/tert-butoxide) not perturbing the integrity of the C-N glycosyl bond. Furthermore, cADPR was successfully synthesized by cyclization of N-1-(5'-phosphoribosyl)ATP catalyzed by NAD(+) pyrophosphorylase in an organic solvent-aqueous medium.

  DOI：

  10.1021/ja00096a002
• 作为产物：
  描述：

  磷酸核糖焦磷酸 、 5’-三磷酸腺苷 在 Escherichia coli pyrophosphatase 、 Campylobacter jejuni adenosine triphosphate phosphoribosyltransferase 、 potassium chloride 、 sodium chloride 、 magnesium chloride 作用下， 以 aq. buffer 为溶剂， 生成 phosphoribosyl ATP
  参考文献：
  名称：

  空肠弯曲菌空肠三磷酸腺苷磷酸核糖基转移酶是一种活性六聚体，通过调节尾部的扭曲来变构控制

  摘要：

  三磷酸腺苷磷酸核糖基转移酶（ATP-PRT）催化植物和微生物中组氨酸生物合成的第一步。在这里，我们介绍了来自致病性空肠弯曲杆菌弯曲杆菌（Cje ATP-PRT）的ATP-PRT的功能和结构特征。该酶是长型（HisG L）ATP-PRT的成员，被组氨酸变构抑制，组氨酸与远程调节域结合，并被AMP竞争性抑制。结晶形式的Cje发现ATP-PRT具有两个截然不同的六聚体构象，在存在底物ATP的情况下观察到开放的同六聚体结构，并且在结合抑制剂组氨酸后出现更紧密的封闭形式。观察到Cje ATP-PRT在溶液中仅采用六聚体四级结构，这与先前的假设相反，后者有利于由低聚物平衡驱动的变构机制。相反，这项研究支持以下结论：ATP-PRT长形六聚体是活性物种。响应于远程组氨酸结合，该结构的收紧导致酶被抑制。

  DOI：

  10.1002/pro.2948

文献信息

• Cyclic ADP-Ribose: Synthesis and Structural Assignment
  作者：Qu-Ming Gu、Charles J. Sih

  DOI：10.1021/ja00096a002

  日期：1994.8

  Cyclic ADP-ribose (cADPR) is a naturally occurring cyclic nucleotide and a potent mediator of calcium mobilization in many mammalian tissues. Previous studies have shown that cADPR is synthesized from beta-NAD(+) via the scission of the nicotinamide-ribose linkage and cyclization by forming a new bond between the ribose and the nitrogen of the adenine ring. However, the position and stereochemistry of this newly formed linkage were not unequivocally determined. In this study we have established that cADPR has the anomeric carbon of the ribose attached onto the N-1-nitrogen of the adenine nucleus via a beta-N-glycosyl linkage. The structural assignment was made by correlating cADPR to N-1-(5'-phosphoribosyl)AMP, a known intermediate of histidine biosynthesis. This was achieved by cleaving the pyrophosphate bond of cADPR under conditions (DMSO/tert-butoxide) not perturbing the integrity of the C-N glycosyl bond. Furthermore, cADPR was successfully synthesized by cyclization of N-1-(5'-phosphoribosyl)ATP catalyzed by NAD(+) pyrophosphorylase in an organic solvent-aqueous medium.
• <i>Campylobacter jejuni</i>adenosine triphosphate phosphoribosyltransferase is an active hexamer that is allosterically controlled by the twisting of a regulatory tail
  作者：Gerd Mittelstädt、Gert-Jan Moggré、Santosh Panjikar、Ali Reza Nazmi、Emily J. Parker

  DOI：10.1002/pro.2948

  日期：2016.8

  phosphoribosyltransferase (ATP‐PRT) catalyzes the first committed step of the histidine biosynthesis in plants and microorganisms. Here, we present the functional and structural characterization of the ATP‐PRT from the pathogenic ε‐proteobacteria Campylobacter jejuni (CjeATP‐PRT). This enzyme is a member of the long form (HisGL) ATP‐PRT and is allosterically inhibited by histidine, which binds to a remote regulatory

  三磷酸腺苷磷酸核糖基转移酶（ATP-PRT）催化植物和微生物中组氨酸生物合成的第一步。在这里，我们介绍了来自致病性空肠弯曲杆菌弯曲杆菌（Cje ATP-PRT）的ATP-PRT的功能和结构特征。该酶是长型（HisG L）ATP-PRT的成员，被组氨酸变构抑制，组氨酸与远程调节域结合，并被AMP竞争性抑制。结晶形式的Cje发现ATP-PRT具有两个截然不同的六聚体构象，在存在底物ATP的情况下观察到开放的同六聚体结构，并且在结合抑制剂组氨酸后出现更紧密的封闭形式。观察到Cje ATP-PRT在溶液中仅采用六聚体四级结构，这与先前的假设相反，后者有利于由低聚物平衡驱动的变构机制。相反，这项研究支持以下结论：ATP-PRT长形六聚体是活性物种。响应于远程组氨酸结合，该结构的收紧导致酶被抑制。