木糖酸 | 526-91-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 木糖酸
• 英文名称: D-xylonic acid
• 英文别名: xylonic acid；(2R,3S,4R)-2,3,4,5-tetrahydroxypentanoic acid
• CAS: 526-91-0
• 化学式: C₅H₁₀O₆
• 分子量: 166.131
• InChiKey: QXKAIJAYHKCRRA-FLRLBIABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  11
• 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：
  118
• 氢给体数：
  5
• 氢受体数：
  6

安全信息

• WGK Germany：
  3
• 储存条件：
  2-8℃

反应信息

• 作为反应物：
  描述：

  木糖酸 在 E. coli DH5α 、 pWN_6.186A 作用下， 以 水 为溶剂， 以25%的产率得到(S)-(-)-1,2,4-丁三醇
  参考文献：
  名称：

  Microbial Synthesis of the Energetic Material Precursor 1,2,4-Butanetriol

  摘要：

  The lack of a route to precursor 1,2,4-butanetriol that is amenable to large-scale synthesis has impeded substitution of 1,2,4-butanetriol trinitrate for nitroglycerin. To identify an alternative to the current commercial synthesis of racemic d,l-1,2,4-butanetriol involving NaBH4 reduction of esterified d,l-malic acid, microbial syntheses of d- and l-1,2,4-butanetriol have been established. These microbial syntheses rely on the creation of biosynthetic pathways that do not exist in nature. Oxidation of d-xylose by Pseudomonas fragi provides d-xylonic acid in 70% yield. Escherichia coli DH5alpha/pWN6.186A then catalyzes the conversion of d-xylonic acid into d-1,2,4-butanetriol in 25% yield. P. fragi is also used to oxidize l-arabinose to a mixture of l-arabino-1,4-lactone and l-arabinonic acid in 54% overall yield. After hydrolysis of the lactone, l-arabinonic acid is converted to l-1,2,4-butanetriol in 35% yield using E. coli BL21(DE3)/pWN6.222A. As a catalytic route to 1,2,4-butanetriol, microbial synthesis avoids the high H2 pressures and elevated temperatures required by catalytic hydrogenation of malic acid.

  DOI：

  10.1021/ja036391+
• 作为产物：
  描述：

  L-木糖 在 copper(II) hydroxide 作用下， 生成 木糖酸
  参考文献：
  名称：

  Nef; Hedenburg; Glattfeld, Journal of the American Chemical Society, 1917, vol. 39, p. 1642

  摘要：

  DOI：
• 作为试剂：
  描述：

  D-木糖 在 sponge type Raney nickel type catalyst 木糖酸 、 氢气 作用下， 以 水 为溶剂， 110.0 ℃ 、5.0 MPa 条件下， 反应 2.5h， 生成 Xylitol
  参考文献：
  名称：

  WO2007/125176

  摘要：

  公开号：

文献信息

• Catalytic dehydrogenation of reducing sugars in alkaline solution
  作者：Gert de Wit、Jan J. de Vlieger、Alida C. Kock-van Dalen、Roelf Heus、Rob Laroy、Antonius J. van Hengstum、Antonius P.G. Kieboom、Herman van Bekkum

  DOI：10.1016/s0008-6215(00)86025-5

  日期：1981.5

  Abstract Aldoses in alkaline medium under the catalytic action of platinum or rhodium are converted into aldonic acids with high selectivity and with concomitant evolution of hydrogen gas. The dehydrogenation reaction has been studied for 25 different mono- and di-saccharides, and is generally applicable for reducing sugars. The influence of several reaction variables has been studied, leading to an

  摘要碱性介质中的醛类在铂或铑的催化作用下被高选择性地转化为醛糖酸，并伴随着氢气的逸出。已经针对25种不同的单糖和二糖研究了脱氢反应，该反应通常可用于还原糖。研究了几个反应变量的影响，得出了一个吸附模型，在该模型中，带负电荷的O-1和H-1与催化剂表面的紧密接触均被视为推动氢化物从C-转移的动力。将1的糖加入催化剂中。
• Selective Conversion of Various Monosaccharaides into Sugar Acids by Additive‐Free Dehydrogenation in Water
  作者：Andres Mollar‐Cuni、Joseph P. Byrne、Pilar Borja、Cristian Vicent、Martin Albrecht、Jose A. Mata

  DOI：10.1002/cctc.202000544

  日期：2020.7.21

  transformation is promoted by highly active and selective catalysts based on iridium(III) complexes containing a triazolylidene (trz) as ligand. Monosaccharides are converted into sugar acids in an easy and sustainable manner using only catalyst and water, and in contrast to previously reported procedures, in the absence of any additive. The reaction is therefore very clean, and highly selective, which avoids the

  五个碳原子和六个碳原子的丰富糖类是生产有价值的平台化学品的有希望的候选者。在这里，我们描述了几种戊糖和己糖的催化脱氢成相应的糖酸，并伴随着分子氢的形成。这种高生物活性的转化是由高活性和选择性的催化剂促进的，该催化剂基于含有三唑基（trz）作为配体的铱（III）配合物。与以前报道的方法相比，在没有任何添加剂的情况下，仅使用催化剂和水，单糖就可以轻松，可持续地转化为糖酸。因此，该反应非常干净且具有高选择性，从而避免了繁琐的纯化和产物分离。机械调查使用11 H NMR和UV光谱以及ESI质谱（ESI-MS）表明形成了前所未有的氢化二铱-氢化物，它对应于催化剂的静止状态。
• Expanding the reaction space of aldolases using hydroxypyruvate as a nucleophilic substrate
  作者：Véronique de Berardinis、Christine Guérard-Hélaine、Ekaterina Darii、Karine Bastard、Virgil Hélaine、Aline Mariage、Jean-Louis Petit、Nicolas Poupard、Israel Sánchez-Moreno、Mark Stam、Thierry Gefflaut、Marcel Salanoubat、Marielle Lemaire

  DOI：10.1039/c6gc02652d

  日期：——

  Aldolases are key biocatalysts for stereoselective C-C bond formation allowing access to polyoxygenated chiral units through direct, efficient, and sustainable synthetic processes. Aldol reaction involving unprotected hydroxypyruvate and an aldehyde...

  醛缩酶是用于形成立体选择性CC键的关键生物催化剂，其允许通过直接，有效和可持续的合成方法获得多加氧手性单元。涉及未保护的羟基丙酮酸和醛的醛醇缩合反应...
• Kinetic behaviour and relative reactivities of some aldoses, amino sugars, and methylated sugars towards platinum(IV) in alkaline medium
  作者：Kalyan Kali Sen Gupta、Bilkis Ara Begum、Biswajit Pal

  DOI：10.1016/s0008-6215(98)00136-0

  日期：1998.6

  The kinetic behaviour and relative reactivities of some carbohydrates (aldoses, amino sugars and methylated sugars) towards platinum(IV) in alkaline medium have been investigated. The reactions are first order with respect to [substrate] and Pt IV . The rates increase with the increase in OH − . The reactions show pseudo-first-order dependence on OH − . The oxidation rates in alkaline medium follow the

  摘要研究了碱性介质中某些碳水化合物（醛糖，氨基糖和甲基化糖）对铂（IV）的动力学行为和相对反应性。对于[底物]和Pt IV，反应是一阶的。比率随着OH-的增加而增加。反应显示出对OH-的伪一阶依赖性。碱性介质中的氧化速率遵循三糖>四糖>戊糖>己糖的顺序。已经计算出反应的活化参数。已经提出了反应的机制。
• Does Locational Choice Matter?
  作者：Subhrajit Guhathakurta、Alvin H. Mushkatel

  DOI：10.1177/10780870022184516

  日期：2000.3

  The authors examine the locational patterns of three subsidized housing programs—conventional project-based, section 8 assisted rental, and shelter plus care supported housing for the severely mentally ill and homeless—in Phoenix, Arizona. They demonstrate that these programs are reinforcing the existing concentrations of the three types of subsidized housing in some Phoenix neighborhoods. The findings for Phoenix suggest that voucher and certificate policies designed to deconcentrate the poor are not achieving some of their major objectives. Indeed, the policies pursued by different providers of subsidized housing may cumulatively lead to increasing concentrations of all such housing in tracts that are already compromised by concentrations of the urban poor.

  作者们研究了亚利桑那州凤凰城三种补贴住房项目的定位模式——传统项目型、第8节辅助租赁和为严重精神病患者和无家可归者提供支持的住房。他们表明，这些项目正在加强凤凰城某些社区现有的三种类型的补贴住房集中。对于凤凰城的研究结果表明，旨在分散贫困人口的券和证书政策并未实现其主要目标之一。事实上，不同补贴住房提供者所追求的政策可能累积导致所有这类住房在已经受到城市贫困人口集中影响的区域中集中增加。