D-arabinono-1,4-lactone 5-(dihydrogenophosphate) | 219946-62-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: D-arabinono-1,4-lactone 5-(dihydrogenophosphate)
• 英文别名: D-arabinono-1,4-lactone 5-phosphate；[(2R,3S,4S)-3,4-dihydroxy-5-oxooxolan-2-yl]methyl dihydrogen phosphate
• CAS: 219946-62-0
• 化学式: C₅H₉O₈P
• 分子量: 228.095
• InChiKey: BBDKIROTABXPPX-JJYYJPOSSA-N

物化性质

• 沸点：
  531.8±33.0 °C(Predicted)
• 密度：
  1.952±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  D-arabinono-1,4-lactone 5-(dihydrogenophosphate) 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以78%的产率得到D-arabinonhydrazide-5-phosphate, monohydrazinium salt
  参考文献：
  名称：

  Competitive inhibitors of yeast phosphoglucose isomerase: synthesis and evaluation of new types of phosphorylated sugars from the synthon d-arabinonolactone-5-phosphate

  摘要：

  Designed as competitive inhibitors of the isomerization reaction catalyzed by the potential chemotherapeutic target phosphoglucose isomerases (PGI), D-arabinonamide-5-phosphate and D-arabinohydrazide-5-phosphate were synthesized and fully characterized. These new types of phosphorylated sugar derivatives were easily and efficiently obtained in a one-step procedure from the promising synthon D-arabinono-1,4-lactone 5-phosphate. These two compounds proved to be new good competitive inhibitors of yeast PGI with the substrate D-fructose-6-phosphate, though not as strong as D-arabinonhydroxamic acid-5-phosphate. Overall, our results are in accord with the postulated 1,2-cis-enediolate species as a probable high-energy intermediate of the PGI-catalyzed reaction. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00100-7
• 作为产物：
  描述：

  在 Dowex 50WX₈-100 、 氢气 作用下， 生成 D-arabinono-1,4-lactone 5-(dihydrogenophosphate)
  参考文献：
  名称：

  Synthesis and evaluation of a new inhibitor of phosphoglucose isomerases: the enediolate analogue 5-phospho-D-arabinohydroxamate

  摘要：

  Designed as a high energy intermediate analogue inhibitor of the potent chemotherapeutic target phosphoglucose isomerases, 5-phospho-D-arabinohydroxamate was efficiently synthesized in a two steps procedure. To date, it proved to be the strongest competitive inhibitor with respect to substrate D-fructose-6-phosphate (K-1 down to 98 nM and K-m/K-i values up to 513). A comparative inhibition study of this compound and other known strong inhibitors on phosphoglucose isomerases from three different sources is also reported. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00621-0

文献信息

• Novel N-substituted 5-phosphate-d-arabinonamide derivatives as strong inhibitors of phosphoglucose isomerases: Synthesis, structure-activity relationship and crystallographic studies
  作者：Lama Ahmad、Stéphane Plancqueel、Noureddine Lazar、Hafsa Korri-Youssoufi、Inès Li de la Sierra-Gallay、Herman van Tilbeurgh、Laurent Salmon

  DOI：10.1016/j.bioorg.2020.104048

  日期：2020.9

  reaction, several of these N-substituted 5-phosphate-d-arabinonamide derivatives appears as new strong PGI inhibitors. For one of them, we report its crystal structure in complex with human PGI at 2.38 Å. Detailed analysis of its interactions at the active site reveals a new binding mode and shows that human PGI is relatively tolerant for modified inhibitors at the “head” C-1 part, offering promising

  磷酸葡萄糖异构酶（PGI）是一种催化d-葡萄糖6-磷酸和d-葡萄糖可逆相互转化的胞质酶-果糖6-磷酸在糖酵解中。在细胞外，PGI也被称为自分泌运动因子（AMF），它是由多种肿瘤细胞分泌的细胞因子，可在体外刺激癌细胞的运动并在体内转移发展。就序列和3D结构而言，人PGI和AMF是严格相同的蛋白质，并且已知AMF活性至少部分地涉及酶活性位点。因此，为了找到新的强AMF-PGI抑制剂，这些抑制剂可能用作基于碳水化合物的电化学生物传感器的抗癌剂和/或生物受体，我们在这项研究中报告了几种衍生的新型人PGI抑制剂的合成和动力学评估。从合成子5 -磷酸d-阿拉伯-1,4-内酯。虽然没有被设计成酶催化异构化反应的高能量中间体类似物抑制剂，几个这些的Ñ取代5-磷酸盐d -arabinonamide衍生物表现为新的强PGI抑制剂。对于其中之一，我们报告了其晶体结构与2.38Å人PGI的复合体。对其在活性位点相