((1R,2R,3S,4R)-4-(3-carbamoylpyridin-1-ium-1-yl)-2,3-dihydroxycyclopentyl)methyl hydrogen phosphate | 132486-54-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: ((1R,2R,3S,4R)-4-(3-carbamoylpyridin-1-ium-1-yl)-2,3-dihydroxycyclopentyl)methyl hydrogen phosphate
• 英文别名: (-)-((1R,2R,3S,4R)-4-(3-carboxamidopyridin-1-yl)-2,3-dihydroxy-1-phosphatoylmethyl)cyclopentane
• CAS: 132486-54-5
• 化学式: C₁₂H₁₇N₂O₇P
• 分子量: 332.25
• InChiKey: SDHOQJJWQXBZPT-DBIOUOCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.17
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  157.02
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ((1R,2R,3S,4R)-4-(3-carbamoylpyridin-1-ium-1-yl)-2,3-dihydroxycyclopentyl)methyl hydrogen phosphate 、 AMP morpholidate 在 2H-tetrazole 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 48.0h， 以1.1g的产率得到
  参考文献：
  名称：

  Stable NAD/NADH derivatives

  摘要：

  本发明提供了公式(I)稳定的烟酰胺腺嘌呤二核苷酸（NAD/NADH）和烟酰胺腺嘌呤二核苷酸磷酸（NADP/NADPH）衍生物，这些衍生物的酶复合物以及它们在生化检测方法和试剂盒中的使用。

  公开号：

  US09399790B2
• 作为产物：
  描述：

  3-carbamoyl-1-(2,4-dinitro-phenyl)-pyridinium 在 磷酸三甲酯 、 N,N-二异丙基乙胺 、 三氯氧磷 作用下， 以 甲醇 为溶剂， 反应 52.0h， 生成 ((1R,2R,3S,4R)-4-(3-carbamoylpyridin-1-ium-1-yl)-2,3-dihydroxycyclopentyl)methyl hydrogen phosphate
  参考文献：
  名称：

  Stable NAD/NADH derivatives

  摘要：

  本发明提供了公式(I)稳定的烟酰胺腺嘌呤二核苷酸（NAD/NADH）和烟酰胺腺嘌呤二核苷酸磷酸（NADP/NADPH）衍生物，这些衍生物的酶复合物以及它们在生化检测方法和试剂盒中的使用。

  公开号：

  US09399790B2

文献信息

• Synthesis of Stable NAD ⁺ Mimics as Inhibitors for the <i>Legionella pneumophila</i> Phosphoribosyl Ubiquitylating Enzyme SdeC
  作者：Jerre M. Madern、Robbert Q. Kim、Mohit Misra、Ivan Dikic、Yong Zhang、Huib Ovaa、Jeroen D. C. Codée、Dmitri V. Filippov、Gerbrand J. Heden van Noort

  DOI：10.1002/cbic.202000230

  日期：2020.10.15

  Modestly modified: Three stable NAD+ analogues namely, c‐NAD+, S‐NAD+ and BAD were prepared by using an optimized chemoenzymatic procedure and were compared side‐by‐side for enzyme inhibition of Legionella effector enzyme SdeC, which is important in bacterial virulence. Minimal structural variation in the furanose ring or nicotinamide part of NAD+ leads to efficient inhibitors.

  修饰程度适中：通过优化的化学酶法制备了三种稳定的NAD +类似物，即c-NAD +，S-NAD +和BAD，并进行了比较，比较了它们对军团菌效应酶SdeC的抑制作用。细菌毒力。NAD +的呋喃糖环或烟酰胺部分的结构变化最小，可产生有效的抑制剂。
• Synthesis of Carba-NAD and the Structures of Its Ternary Complexes with SIRT3 and SIRT5
  作者：Bruce G. Szczepankiewicz、Han Dai、Karsten J. Koppetsch、Dongming Qian、Fan Jiang、Cheney Mao、Robert B. Perni

  DOI：10.1021/jo301067e

  日期：2012.9.7

  Carba-NAD is a synthetic compound identical to NAD except for one substitution, where an oxygen atom adjacent to the anomeric linkage bearing nicotinamide is replaced with a methylene group. Because it is inert in nicotinamide displacement reactions, carba-NAD is an unreactive substrate analogue for NAD-consuming enzymes. SIRT3 and SIRT5 are NAD-consuming enzymes that are potential therapeutic targets for the treatment of metabolic diseases and cancers. We report an improved carba-NAD synthesis, including a pyrophosphate coupling method that proceeds in approximately 60% yield. We also disclose the Xray crystal structures of the ternary complexes of SIRT3 and SIRT5 bound to a peptide substrate and carba-NAD. These X-ray crystal structures provide critical snapshots of the mechanism by which human sirtuins function as protein deacylation catalysts.