4,5-dihydroxypentane-2,3-dione

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,5-dihydroxypentane-2,3-dione
• 英文别名: 1-deoxypentosone；ent-DPD；(4R)-4,5-dihydroxypentane-2,3-dione；(R)-4,5-dihydroxy-2,3-pentadione；4,5-dihydroxy-2,3-pentanedione；(R)-DPD；(R)-4,5-Dihydroxypentane-2,3-dione
• 化学式: C₅H₈O₄
• 分子量: 132.116
• InChiKey: UYTRITJAZOPLCZ-SCSAIBSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  邻苯二胺 、 4,5-dihydroxypentane-2,3-dione 以 water-d2 为溶剂， 生成 <(1'S)-2-(1',2'-dihydroxyethyl)-3-methylquinoxaline>
  参考文献：
  名称：

  Synthesis and bioluminescence-inducing properties of autoinducer (S)-4,5-dihydroxypentane-2,3-dione and its enantiomer

  摘要：

  The autoinducer (4S)-4,5-dihydroxypentane-2,3-dione ((S)-DPD, AI-2) facilitates chemical communication, termed 'quorum sensing', amongst a wide range of bacteria, The synthesis of (S)-DPD is challenging in part due to its instability. Herein we report a novel synthesis of (S)-DPD via (2S)-2,3-O-isopropylidene glyceraldehyde, through Wittig, dihydroxylation and oxidation reactions, with a complimentary asymmetric synthesis to a key precursor. Its enantiomer (R)-DPD, was prepared from D-mannitol via (2R)2,3-O-isopropylideneglyceraldehyde. The synthesized enantiomers of DPD have AI-2 bioluminescenceinducing properties in the Vibrio harveyi BB170 strain. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.02.064
• 作为产物：
  描述：

  1-(tert-butyldiphenylsilyloxy)pent-3-yne-2-one 在 sodium periodate 、 B-isopinocampheyl-9-borabicyclo[3.3.1]nonane 、 ruthenium(IV) oxide hydrate 、 硫酸 、 四丁基氟化铵 、 水 作用下， 以 四氢呋喃 、 四氯化碳 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 49.0h， 生成 4,5-dihydroxypentane-2,3-dione
  参考文献：
  名称：

  An efficient synthesis of the precursor of AI-2, the signalling molecule for inter-species quorum sensing

  摘要：

  Autoinducer-2 (AI-2) is a signalling molecule for bacterial inter-species communication. A synthesis of (S)-4,5-dihydroxypentane-2,3-dione (DPD), the precursor of AI-2, is described starting from methyl glycolate. The key step was an asymmetric reduction of a ketone with (S)-Alpine borane. This new method was highly reproducible affording DPD for biological tests without contaminants. The biological activity was tested with the previously available assays and compared with a new method using an Escherichia coli reporter strain thus avoiding the use of the pathogenic Salmonella reporter. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.12.036

文献信息

• Degradation of Glucose: Reinvestigation of Reactive α-Dicarbonyl Compounds^†
  作者：Jenny Gobert、Marcus A. Glomb

  DOI：10.1021/jf9019085

  日期：2009.9.23

  to give stable quinoxalines of d-arabino-hexos-2-ulose (glucosone), N6-(3,6-dideoxyhexos-2-ulos-6-yl)-l-lysine, 1-deoxy-d-erythro-2,3-hexodiulose (1-deoxyglucosone), 3-deoxy-d-erythro-hexos-2-ulose (3-deoxyglucosone), ethanedial (glyoxal), 2-oxopropanal (methylglyoxal), 3,4-dihydroxy-2-oxobutanal (threosone), 1-hydroxy-2,3-butanedione (1-deoxythreosone), 4-hydroxy-2-oxobutanal (3-deoxythreosone), 4,

  美拉德反应以重要方式影响加工食品中风味和颜色的形成。还原糖和氨基酸最终会与稳定的最终产物发生反应。为了阐明复杂的形成途径，已经发表了大量实验。α-二羰基化合物被认为是重要的关键中间体。在目前的工作中，对赖氨酸存在下的美拉德葡萄糖降解进行了重新研究。用邻苯二胺捕获α-二羰基化合物，得到稳定的d-阿拉伯-己基-2-己糖（葡糖酮），N 6-（3,6-二脱氧己基-2-ulos-6-基）-1-赖氨酸的喹喔啉，1-deoxy- d - erythro-2,3-己二糖（1-脱氧葡糖酮），3- deoxy- d-赤-己基-2-ulose（3-脱氧葡糖酮），乙二醛（乙二醛），2-氧丙醛（甲基乙二醛），3,4-二羟基-2 -oxobutanal（苏糖松），1-hydroxy-2,3-butanedione（1-deoxythreosone），4-hydroxy-2-oxobutanal（3-deoxythreosone），4
• <i>N</i>-(1-Deoxy-<scp>d</scp>-xylulos-1-yl)-glutathione: A Maillard Reaction Intermediate Predominating in Aqueous Glutathione-Xylose Systems by Simultaneous Dehydration-Reaction
  作者：Wei Tang、Heping Cui、Fuli Sun、Xiaohong Yu、Khizar Hayat、Shahzad Hussain、Muhammad Usman Tahir、Xiaoming Zhang、Chi-Tang Ho

  DOI：10.1021/acs.jafc.9b04694

  日期：2019.8.14

  The effect of simultaneous dehydration-reaction (SDR) on Amadori rearrangement product (ARP) N-(1-deoxy-d-xylulos-1-yl)-glutathione and its key degradation products, 3-deoxyxylosone (3-DX) and 1-deoxyxylosone (1-DX), were investigated in an aqueous glutathione-xylose (GSH-Xyl) system. The yield of ARP was increased to 67.98% by SDR compared with 8.44% by atmospheric thermal reaction at 80 °C. Reaction

  同时脱水反应（SDR）对Amadori重排产物（ARP）N-（1-deoxy- d在含水谷胱甘肽-木糖（GSH-Xyl）系统中研究了-xylulos-1-yl）-谷胱甘肽及其主要降解产物3-deoxyxylosone（3-DX）和1-deoxyxylosone（1-DX）。通过SDR将ARP的收率提高到67.98％，而在80°C下通过大气热反应将ARP的收率提高到8.44％。应用反应动力学分析了SDR条件下ARP形成和降解的机理和特征。ARP的形成和降解速率高度依赖于温度，而后者对温度更敏感。通过调节温度和pH的反应条件，可以控制ARP形成速率常数与降解速率常数的比值，从而实现通过SDR从GSH-Xyl Maillard反应中高效制备ARP。
• Synergistic Effect of a Thermal Reaction and Vacuum Dehydration on Improving Xylose–Phenylalanine Conversion to <i>N</i>-(1-Deoxy-<scp>d</scp>-xylulos-1-yl)-phenylalanine during an Aqueous Maillard Reaction
  作者：Heping Cui、Khizar Hayat、Chengsheng Jia、Emmanuel Duhoranimana、Qingrong Huang、Xiaoming Zhang、Chi-Tang Ho

  DOI：10.1021/acs.jafc.8b04448

  日期：2018.9.26

  The synergistic effect of a thermal reaction and vacuum dehydration on the conversion of xylose (Xyl) and phenylalanine (Phe) to a Maillard-reaction intermediate (MRI) was researched. The yield of N-(1-deoxy-α-d-xylulos-1-yl)-phenylalanine was successfully improved and increased from 13.62 to 47.23% through the method combining a thermal reaction and vacuum dehydration. A dynamic process was involved

  研究了热反应和真空脱水对木糖（Xyl）和苯丙氨酸（Phe）向美拉德反应中间体（MRI）转化的协同作用。通过热反应和真空脱水相结合的方法，成功地提高了N-（1-脱氧-α- d-木氟-1-基）-苯丙氨酸的收率，从13.62％提高到47.23％。一个动态过程涉及到Xyl和Phe（Xyl-Phe）到N-取代的d-木糖胺的转化以及N-取代的d-木糖胺到N-（1-deoxy-α- d -xylulos-1）的转化脱水初期的-yl）-苯丙氨酸；然后，只有N-取代的d的转化在最后阶段发生了将木糖胺合成为N-（1-脱氧-α- d-木酮-1-基）-苯丙氨酸的过程。此外，在最佳条件（90°C和pH 7.4）下制备MRI，并通过ESI质谱和NMR对获得的MRI进行表征和确认。
• An Expeditious Synthesis of DPD and Boron Binding Studies
  作者：Martin F. Semmelhack、Shawn R. Campagna、Michael J. Federle、Bonnie L. Bassler

  DOI：10.1021/ol047695j

  日期：2005.2.1

  A practical synthesis has been developed for DPD (4,5-dihydroxypentane-2,3-dione), an unstable small molecule that is proposed to be the source of universal signaling agents for quorum sensing in bacteria. The synthesis allows preparation of isotopically labeled DPD and entDPD as well as detailed studies of spontaneous binding to borate to give the unusual borate complex 6, the signal for marine bacteria such as Vibrio harveyi.
• Synthesis and bioluminescence-inducing properties of autoinducer (S)-4,5-dihydroxypentane-2,3-dione and its enantiomer
  作者：Manikandan Kadirvel、William T. Stimpson、Souad Moumene-Afifi、Biljana Arsic、Nicola Glynn、Nigel Halliday、Paul Williams、Peter Gilbert、Andrew J. McBain、Sally Freeman、John M. Gardiner

  DOI：10.1016/j.bmcl.2010.02.064

  日期：2010.4

  The autoinducer (4S)-4,5-dihydroxypentane-2,3-dione ((S)-DPD, AI-2) facilitates chemical communication, termed 'quorum sensing', amongst a wide range of bacteria, The synthesis of (S)-DPD is challenging in part due to its instability. Herein we report a novel synthesis of (S)-DPD via (2S)-2,3-O-isopropylidene glyceraldehyde, through Wittig, dihydroxylation and oxidation reactions, with a complimentary asymmetric synthesis to a key precursor. Its enantiomer (R)-DPD, was prepared from D-mannitol via (2R)2,3-O-isopropylideneglyceraldehyde. The synthesized enantiomers of DPD have AI-2 bioluminescenceinducing properties in the Vibrio harveyi BB170 strain. (C) 2010 Elsevier Ltd. All rights reserved.