2-脱氢-3-脱氧-6-磷酸-D-葡萄糖酸 | 27244-54-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 中文名称: 2-脱氢-3-脱氧-6-磷酸-D-葡萄糖酸
• 英文名称: 3-deoxy-D-erythro-hex-2-ulosonic acid 6-phosphate
• 英文别名: 2-keto-3-deoxy-6-phosphogluconate；2-Keto-3-deoxy-6-phosphogluconic acid；(4S,5R)-4,5-dihydroxy-2-oxo-6-phosphonooxyhexanoic acid
• CAS: 27244-54-8
• 化学式: C₆H₁₁O₉P
• 分子量: 258.122
• InChiKey: OVPRPPOVAXRCED-WVZVXSGGSA-N

物化性质

• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  -3.4
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  162
• 氢给体数：
  5
• 氢受体数：
  9

安全信息

• 海关编码：
  2931900090
• WGK Germany：
  3
• 储存条件：
  -20°C，密封保存，并置于干燥处。

反应信息

• 作为反应物：
  描述：

  2-脱氢-3-脱氧-6-磷酸-D-葡萄糖酸 在 Saccharophagus degradans 2-40^T 2-keto-3-deoxy-phosphogluconate aldolase 作用下， 以 aq. buffer 为溶剂， 反应 1.0h， 生成 丙酮酸
  参考文献：
  名称：

  Validation of the metabolic pathway of the alginate-derived monomer in Saccharophagus degradans 2-40 T by gas chromatography–mass spectrometry

  摘要：

  Marine macroalgae are potential resources for the sustainable production of biofuels and bio-based chemicals. Alginate, a major component of brown macroalgae, consists of two uronate monomers, which are further non-enzymatically converted to 4-deoxy-L-erythro-5-hexoseulose uronate (DEH). In several marine bacteria, DEH is known to be metabolized via three enzymatic steps, consisting of DEH reductase, 2-keto-3-deoxy-n-gluconate (KDG) kinase, and 2-keto-3-deoxy-phosphogluconate (KDPG) aldolase, which yields two glycolytic intermediates: D-glyceraldehyde-3-phosphate and pyruvate. However, such functions of these enzymes for the DEH pathway have rarely been experimentally validated. In the present study, the DEH metabolic pathway was investigated in Saccharophagus degradans 2-40(T), a marine bacterium that utilizes alginate. Through in vitro tests assisted by gas chromatography/mass spectrometry and gas chromatography/time-of-flight mass spectrometry, the purified enzymes were functionally confirmed and annotated as dehR, kdgK, and kdpgA, respectively. In conclusion, we report the in vitro validation of the metabolic pathway of DEH monomerized from alginate. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.procbio.2016.07.020
• 作为产物：
  描述：

  生成 2-脱氢-3-脱氧-6-磷酸-D-葡萄糖酸
  参考文献：
  名称：

  Trigalo; Jachymczyk; Young, Journal of the Chemical Society. Perkin transactions I, 1975, # 6, p. 593 - 598

  摘要：

  DOI：

文献信息

• CONVERSION OF HEXURONIC ACID TO HEXARIC ACID
  申请人：Boer Harry

  公开号：US20120045804A1

  公开（公告）日：2012-02-23

  The present invention relates to a method and microbial host strain for converting a hexuronic acid to a hexaric acid. In particular, the invention relates to the con-version of D-galacturonic acid to meso-galactaric acid (mucic acid). The invention also concerns an isolated nucleotide sequence. According to the present method a microbial host strain genetically modified to express uronate dehydrogenase enzyme (EC 1.1.1.203) is contacted with a biomaterial comprising hexuronic acid and the con-version products are recovered. By using the recombinant microorganisms of the present invention it is possible to treat biomaterials comprising hexuronic acids and thereby decrease the amount of hexuronic acids released to the environment.

  本发明涉及一种将六羟基酸转化为六环酸的方法和微生物宿主菌株。具体而言，本发明涉及将D-半乳糖酸转化为中间-半乳糖酸（粘液酸）的转化。本发明还涉及一种分离的核苷酸序列。根据本方法，将经过基因修饰以表达尿酸脱氢酶酶（EC 1.1.1.203）的微生物宿主菌株与含有六羟基酸的生物材料接触，并回收转化产物。通过使用本发明的重组微生物，可以处理含有六羟基酸的生物材料，从而减少释放到环境中的六羟基酸的数量。
• Slow-binding inhibition of 2-keto-3-deoxy-6-phosphogluconate (KDPG) aldolase
  作者：Rémi Braga、Laurence Hecquet、Casimir Blonski

  DOI：10.1016/j.bmc.2004.03.039

  日期：2004.6

  2-Keto-3-deoxy-6-phosphogluconate (KDPG) aldolase is a key enzyme in the Entner-Doudoroff pathway of bacteria. It catalyzes the reversible production of KDPG from pyruvate and D-glyceraldehyde 3-phosphate through a class I Schiff base mechanism. On the basis of aldolase mechanistic pathway, various pyruvate analogues bearing beta-diketo structures were designed and synthesized as potential inhibitors. Their capacity to inhibit aldolase catalyzed reaction by forming stabilized iminium ion or conjugated enamine were investigated by enzymatic kinetics and UV-vis difference spectroscopy. Depending of the substituent R (methyl or aromatic ring), a competitive or a slow-binding inhibition takes place. These results were examined on the basis of the three-dimensional structure of the enzyme. (C) 2004 Elsevier Ltd. All rights reserved.
• Microbial synthesis of 3-deoxy-d-erythro-hex-2-ulosonic acid 6-phosphate
  作者：Bernd R. Knappmann、Mohamed A. El-Nawawy、Hans G. Schlegel、Maria-Regina Kula

  DOI：10.1016/0008-6215(93)80029-e

  日期：1993.4

  A microbial route was explored for the synthesis of 3-deoxy-D-erythro-hex-2-ulosonic acid 6-phosphate (2-keto-3-deoxy-6-phosphogluconate, KDPG). Two strains of bacteria, Alcaligenes eutrophus H16 F34 (DSM 529) and Escherichia coli DF 71 (CGSC 4880), lacking in KDPG-aldolase activity were tested for excretion of KDPG. Using pyruvate and gluconate as carbon sources, Alcaligenes eutrophus H16 F34 accumulated and excreted 3-deoxy-D-erythro-hexulosonic acid 6-phosphate into the culture broth, while the E. coli strain, using pyruvate and glucuronate, failed. KDPG was isolated from the culture supernatant of Alcaligenes eutrophus H16 F34 in 78% yield and 5 g scale with respect to the consumed gluconate.
• US8895273B2
  申请人：——

  公开号：US8895273B2

  公开（公告）日：2014-11-25
• [EN] CONVERSION OF HEXURONIC ACID TO HEXARIC ACID<br/>[FR] CONVERSION D'ACIDE HEXURONIQUE EN ACIDE HEXARIQUE
  申请人：VALTION TEKNILLINEN

  公开号：WO2010072902A1

  公开（公告）日：2010-07-01

  The present invention relates to a method and microbial host strain for converting a hexuronic acid to a hexaric acid. In particular, the invention relates to the con- version of D-galacturonic acid to meso-galactaric acid (mucic acid). The invention also concerns an isolated nucleotide sequence. According to the present method a microbial host strain genetically modified to express uronate dehydrogenase enzyme (EC 1.1.1.203)is contacted with a biomaterial comprising hexuronic acid and the conversion products are recovered. By using the recombinant microorganisms of the present invention it is possible to treat biomaterials comprising hexuronic acids and thereby decrease the amount of hexuronic acids released to the environment.