5,6-dideoxy-D-threo-hex-2-ulose | 117625-98-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 5,6-dideoxy-D-threo-hex-2-ulose
• 英文别名: 5,6-dideoxy-D-2-threo-hexulose；5,6-dideoxy-D-threo-2-hexulose；5,6-dideoxy-D-threo-hexulose；5,6-dideoxy-D-threohexulose；xylulose；D-threo-5,6-dideoxy-[2]hexulose；5,6-Dideoxy-d-fructose；(3S,4R)-1,3,4-trihydroxyhexan-2-one
• CAS: 117625-98-6
• 化学式: C₆H₁₂O₄
• 分子量: 148.159
• InChiKey: VLNMULGCQJQMTL-XINAWCOVSA-N

物化性质

• 沸点：
  336.3±27.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,6-dideoxy-D-threo-hex-2-ulose 在 sodium tetrahydroborate 、 sodium periodate 、 zinc(II) iodide 作用下， 以 四氢呋喃 、 乙醇 、 水 、 丙酮 为溶剂， 生成
  参考文献：
  名称：

  A transketolase-based synthesis of (+)-exo-brevicomin

  摘要：

  The naturally occurring beetle pheromone (+)-exo-brevicomin was synthesized by a strategy combining chemical and enzymatic steps. The commercially available enzyme transketolase (EC 2.2.1.1) catalyzed the condensation of beta-hydroxypyruvic acid and 2-hydroxybutyraldehyde to furnish the central intermediate in the sequence, optically active hydroxyketone 5. A short sequence converted ketose 5 to protected aldose 8. Wittig extension of the aldehyde followed by hydrogenation and ketal hydrolysis generated the title compound.

  DOI：

  10.1016/s0040-4039(00)93473-7
• 作为产物：
  描述：

  O¹-phosphono-D-threo-5,6-dideoxy-[2]hexulose 生成 5,6-dideoxy-D-threo-hex-2-ulose
  参考文献：
  名称：

  A transketolase-based synthesis of (+)-exo-brevicomin

  摘要：

  The naturally occurring beetle pheromone (+)-exo-brevicomin was synthesized by a strategy combining chemical and enzymatic steps. The commercially available enzyme transketolase (EC 2.2.1.1) catalyzed the condensation of beta-hydroxypyruvic acid and 2-hydroxybutyraldehyde to furnish the central intermediate in the sequence, optically active hydroxyketone 5. A short sequence converted ketose 5 to protected aldose 8. Wittig extension of the aldehyde followed by hydrogenation and ketal hydrolysis generated the title compound.

  DOI：

  10.1016/s0040-4039(00)93473-7

文献信息

• A SYNTHESIS OF 5,6-DIDEOXY-<scp>D</scp>-XYLOHEXOSE(5-DEOXY-5-<i>C</i>-METHYL-<scp>D</scp>-XYLOSE)
  作者：J. K. N. Jones、J. L. Thompson

  DOI：10.1139/v57-130

  日期：1957.9.1

  A synthesis of 5,6-dideoxy-D-xylohexose (I) from D-glucose is described. The action of sodium iodide in acetone on some toluene-p-sulphonyl esters of sugar derivatives is detailed.

  描述了从 D-葡萄糖合成 5,6-二脱氧-D-木己糖 (I)。详细介绍了丙酮中的碘化钠对某些糖衍生物的甲苯-对磺酰基酯的作用。
• Genome Mining for Innovative Biocatalysts: New Dihydroxyacetone Aldolases for the Chemist’s Toolbox
  作者：Christine Guérard-Hélaine、Véronique de Berardinis、Marielle Besnard-Gonnet、Ekaterina Darii、Marine Debacker、Adrien Debard、Carlos Fernandes、Virgil Hélaine、Aline Mariage、Virginie Pellouin、Alain Perret、Jean-Louis Petit、Martine Sancelme、Marielle Lemaire、Marcel Salanoubat

  DOI：10.1002/cctc.201500014

  日期：2015.6.15

  Stereoselective carboligating enzymes were discovered by a genome mining approach to extend the biocatalysis toolbox. Seven hundred enzymes were selected by sequence comparison from diverse prokaryotic species as representatives of the aldolase (FSA) family diversity. The aldol reaction tested involved dihydroxyacetone (DHA) and glyceraldehyde‐3‐phosphate. The hexose‐6‐phosphate formation was monitored

  通过基因组挖掘方法发现了立体选择性碳连接酶，以扩展生物催化工具箱。通过序列比较从多种原核物种中选择了700种酶，作为醛缩酶（FSA）家族多样性的代表。测试的醛醇缩合反应涉及二羟基丙酮（DHA）和3-磷酸甘油醛。通过质谱监测己糖-6-磷酸盐的形成。发现标注为反醛糖酶或醛缩酶的十八种酶表现出DHA醛缩酶活性。值得注意的是，其中六个被证明是醛缩酶，而不是醛缩酶，与目前描述的相似性非常有限。对所有酶进行的多序列比对揭示了在FSA大肠杆菌中发现的新DHA醛缩酶中的Tyr而不是通常在转醛酶中发现的Phe。与FSA大肠杆菌相比，这些DHA醛缩醛酶中的4种具有生化特性。特别地，来自单核细胞增生性李斯特菌的醛缩酶表现出令人感兴趣的催化性质。
• Rabbit muscle aldolase as a catalyst in organic synthesis
  作者：Mark D. Bednarski、Ethan S. Simon、Norbert Bischofberger、Wolf Dieter Fessner、Mahn Joo Kim、Watson Lees、Tohru Saito、Herbert Waldmann、George M. Whitesides

  DOI：10.1021/ja00184a034

  日期：1989.1

  and 1,4-d ihydroxy-3-butanonel -phosphonate (69)-o f I I DHAP analogues tcs tcd weic substrates for RA\A. neVn is stable under tire reattion conditions used in synthetic applications: it withstands organic cosolvents (up to 207o D\1SO or EIOH); i t can be uscd in immobil ized iorm, in soluble form, or enclosed within a mcmbranc; i t is a lso a i r -s tab le . Synthcscs of 5 ,6-d ideoxy-Dthreo-2-hexulose

  Abst6ct : 来自拉比肌肉的 p-Fructosc-1,6-b 是磷酸缩醛酶 (RA\tA, EC 4.1.2 l3) DHAP, l) 和 aldehl 'des 具有一系列结构。本文证明了超过 50 种醛类 [除其天然底物外，> 甘油醛 3-phcPFtc' G-3-P (2) l arc iu6st rate for RAMA。不受阻碍的脂族、α-杂芳基取代的、不同的保护性的醇和氨基醛是取代物；空间位阻的脂族和α，6-不饱和醛不是。芳香醛要么是低效的底物，要么不反应。磷酸化的醛比未磷酸化的对应物反应得更快，并且在a 位置被电子负性基团取代的醛比未取代的脂肪族醛反应更快。DHAP 部分结构中的允许变化受到更多限制；仅 2-I,3' 二羟基-2-丁酮 3-磷酸酯 (68) 和 1,4-二羟基-3-丁酮-膦酸酯 (69)-II DHAP 类似物 tcs tcd weic 用于 RA\A
• One-pot four-enzyme synthesis of ketoses with fructose 1,6-bisphosphate aldolases from Staphylococcus carnosus and rabbit muscle
  作者：Zijie Li、Li Cai、Mohui Wei、Peng George Wang

  DOI：10.1016/j.carres.2012.05.007

  日期：2012.8

  By the action of D-fructose 1,6-bisphosphate aldolases (FruA) from rabbit muscle and Staphylococcus carnosus, various ketoses were synthesized from glyceraldehydes or other aliphatic aldehydes as acceptors in a one-pot four-enzyme system.

  通过来自兔肌肉和葡萄球菌的D-果糖1,6-二磷酸醛缩酶（FruA）的作用，在一站式四酶系统中由甘油醛或其他脂族醛作为受体合成了各种酮糖。
• Synthesis of non-natural carbohydrates from glycerol and aldehydes in a one-pot four-enzyme cascade reaction
  作者：Lara Babich、Lieke J. C. van Hemert、Aleksandra Bury、Aloysius F. Hartog、Pierpaolo Falcicchio、John van der Oost、Teunie van Herk、Ron Wever、Floris P. J. T. Rutjes

  DOI：10.1039/c1gc15429j

  日期：——

  A simple procedure has been developed for the synthesis of enantio- and diastereomerically pure carbohydrate analogues from glycerol and a variety of aldehydes in one pot using a four-enzyme cascade reaction. As a proof of concept of the usefulness of this enzymatic catalytic cascade the naturally occurring azasugarD-fagomine was synthesized. This work highlights the potential value of using enzymes in cascade reactions to selectively form complex products that by previous traditional organic chemistry could only be obtained via repeated isolation and purification of intermediates.

  已经开发出一种简单的程序，用于通过四酶级联反应在一个反应瓶中从甘油和多种醛类合成对映体和非对映体纯的糖类类似物。作为这种酶催化级联反应有用性的概念验证，合成了天然存在的氨基糖D-fagomine。这项工作强调了在级联反应中使用酶的潜在价值，以选择性地形成复杂产物，而这些产物在以往传统有机化学中只能通过反复分离和纯化中间体获得。