D-arabinohydroxamic acid

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: D-arabinohydroxamic acid
• 英文别名: (2S,3R,4R)-N,2,3,4,5-Pentahydroxypentanamide
• 化学式: C₅H₁₁NO₆
• 分子量: 181.145
• InChiKey: AGVYHANDLPZRFS-JJYYJPOSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.5
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  130
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,3-二氟-6-硝基苯胺 在 palladium on activated charcoal sodium hydroxide 、 氢气 、 silver nitrate 、 二乙胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 生成 D-arabinohydroxamic acid
  参考文献：
  名称：

  D-木糖异构酶的有效抑制剂D-阿拉伯糖基异羟肟酸和D-苏糖异羟肟酸的合成

  摘要：

  D-木糖异构酶的两种有效抑制剂：D-苏糖异羟肟酸2和D-阿拉伯糖异羟酰胺酸3通过将D-阿拉伯糖转化为D-阿拉伯酸的受保护衍生物并通过与O-苄基羟胺偶联引入异羟肟酸酯基团而合成。 。

  DOI：

  10.1016/0040-4039(96)00254-7

文献信息

• A convenient preparation of aldonohydroxamic acids in water and crystal structure of l-erythronohydroxamic acid
  作者：Laurent Salmon、Elise Prost、Claude Merienne、Renaud Hardré、Georges Morgant

  DOI：10.1016/s0008-6215(01)00210-5

  日期：2001.10

  Hydroxamic acids derived from aldonic acids, namely aldonohydroxamic acids, have become an increasingly important class of inhibitors of enzymes involved in the metabolism of carbohydrates. We now report the straightforward preparation of various types of aldonohydroxamic acids by a new methodology involving the use of commercial 50% aqueous hydroxylamine as the source of the free base hydroxylamine that reacts directly with the corresponding aldonolactone dissolved in water. The reaction proceeds almost instantaneously in water at room temperature, yielding generally pure products in quantitative yield. To date, this methodology is probably the most facile and efficient way to synthesize aldonohydroxamic acids. We also determined by X-ray diffraction analysis the first crystal structure of a free aldonohydroxamic acid reported to date. Crystals of L-erythronohydroxamic acid belonged to the monoclinic system, space group P2(1), a = 5.511(3), b = 7.556(1), c = 8.071(3) Angstrom, beta = 109.10 degrees, and Z = 2. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Synthesis of D-arabinohydroxamic acid and D-threonohydroxamic acid, potent inhibitors of D-xylose isomerases
  作者：Alain Gaudemer、Catherine Fanet、Françoise Gaudemer、Laurent Salmon

  DOI：10.1016/0040-4039(96)00254-7

  日期：1996.3

  Two potent inhibitors of D-xylose isomerases: D-threonohydroxamic acid 2 and D-arabinohydroxamic acid 3 have been synthesized by conversion of D-arabinose to a protected derivative of D-arabinonic acid and introduction of the hydroxamate group by coupling with O-benzylhydroxylamine.

  D-木糖异构酶的两种有效抑制剂：D-苏糖异羟肟酸2和D-阿拉伯糖异羟酰胺酸3通过将D-阿拉伯糖转化为D-阿拉伯酸的受保护衍生物并通过与O-苄基羟胺偶联引入异羟肟酸酯基团而合成。 。