1-((1R,2S,3R,4R)-4-((((((((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)hydroxyphosphoryl)oxy)oxidophosphoryl)oxy)methyl)-2,3-dihydroxycyclopentyl)-3-carbamoylpyridin-1-ium | 112345-60-5

• 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: 1-((1R,2S,3R,4R)-4-((((((((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)hydroxyphosphoryl)oxy)oxidophosphoryl)oxy)methyl)-2,3-dihydroxycyclopentyl)-3-carbamoylpyridin-1-ium
• 英文别名: Carbanicotinamide adenine dinucleotide；[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(1R,2R,3S,4R)-4-(3-carbamoylpyridin-1-ium-1-yl)-2,3-dihydroxycyclopentyl]methyl phosphate
• CAS: 112345-60-5
• 化学式: C₂₂H₂₉N₇O₁₃P₂
• 分子量: 661.459
• InChiKey: DGPLSUKWXXSBCU-VGXGLJSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.4
• 重原子数：
  44
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  312
• 氢给体数：
  7
• 氢受体数：
  17

反应信息

• 作为产物：
  描述：

  (-)-文斯内酯 在 吡啶 、 磷酸三甲酯 、 盐酸 、 四氧化锇 、 sodium acetate 、 三乙基硼氢化锂 、 对甲苯磺酸 、 formamide 、 N-甲基吗啉氧化物 、 manganese(ll) chloride 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 、 异戊醇 、 水 、 叔丁醇 为溶剂， 反应 40.67h， 生成 1-((1R,2S,3R,4R)-4-((((((((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)hydroxyphosphoryl)oxy)oxidophosphoryl)oxy)methyl)-2,3-dihydroxycyclopentyl)-3-carbamoylpyridin-1-ium
  参考文献：
  名称：

  Synthesis of Carba-NAD and the Structures of Its Ternary Complexes with SIRT3 and SIRT5

  摘要：

  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.

  DOI：

  10.1021/jo301067e

文献信息

• [EN] METHOD AND SUBSTANCES FOR PREPARATION OF N-SUBSTITUTED PYRIDINIUM COMPOUNDS<br/>[FR] PROCÉDÉ ET SUBSTANCES POUR PRÉPARER DES COMPOSÉS DE PYRIDINIUM À SUBSTITUTION N
  申请人：ROCHE DIAGNOSTICS GMBH

  公开号：WO2011012269A3

  公开（公告）日：2011-08-11
• SIRT1 INHIBITORS AND STEM CELL REJUVENATION
  申请人：City of Hope

  公开号：US20150044184A1

  公开（公告）日：2015-02-12

  Provided herein are, inter alia, methods and compositions for treating or preventing diseases using SIRT1 inhibitors. The methods provided herein are particularly useful for treating or preventing age-related hematological diseases as well as cancerous hematological diseases. Further provided herein are hematopoietic cells useful for treating or preventing hematological diseases.
• US9987280B2
  申请人：——

  公开号：US9987280B2

  公开（公告）日：2018-06-05