(2R,3S)-2,3-Dihydroxy-5-oxo-hexanedioic acid | 687-56-9

• 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
• 英文名称: (2R,3S)-2,3-Dihydroxy-5-oxo-hexanedioic acid
• 英文别名: 5-dehydro-4-deoxy-D-glucaric acid；(2R,3S)-2,3-dihydroxy-5-oxohexanedioic acid
• CAS: 687-56-9
• 化学式: C₆H₈O₇
• 分子量: 192.125
• InChiKey: QUURPCHWPQNNGL-ZAFYKAAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  132
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2R,3S)-2,3-Dihydroxy-5-oxo-hexanedioic acid 在 Agrobacterium tumefaciens keto-deoxy-D-galactarate dehydratase 、 水 作用下， 以 aq. buffer 为溶剂， 反应 0.5h， 生成 2,5-dioxopentanoic acid
  参考文献：
  名称：

  Structure and Function of a Decarboxylating Agrobacterium tumefaciens Keto-deoxy-d-galactarate Dehydratase

  摘要：

  Agrobacterium tumefaciens (At) strain C58 contains an oxidative enzyme pathway that can function on both d-glucuronic and d-galacturonic acid. The corresponding gene coding for At keto-deoxy-d-galactarate (KDG) dehydratase is located in the same gene cluster as those coding for uronate dehydrogenase (At Udh) and galactarolactone cycloisomerase (At Gci) which we have previously characterized. Here, we present the kinetic characterization and crystal structure of At KDG dehydratase, which catalyzes the next step, the decarboxylating hydrolyase reaction of KDG to produce a-ketoglutaric semialdehyde (alpha-KGSA) and carbon dioxide. The crystal structures of At KDG dehydratase and its complexes with pyruvate and 2-oxoadipic acid, two substrate analogues, were determined to 1.7 angstrom 1.5 angstrom, and 2.1 angstrom resolution, respectively. Furthermore, mass spectrometry was used to confirm reaction end-products. The results lead us to propose a structure-based mechanism for At KDG dehydratase, suggesting that while the enzyme belongs to the Class I aldolase protein family, it does not follow a typical retro-aldol condensation mechanism.

  DOI：

  10.1021/bi501290k
• 作为产物：
  描述：

  D-saccharate 生成 (2R,3S)-2,3-Dihydroxy-5-oxo-hexanedioic acid
  参考文献：
  名称：

  Evolution of Enzymatic Activities:  Multiple Pathways for Generating and Partitioning a Common Enolic Intermediate by Glucarate Dehydratase from Pseudomonas putida

  摘要：

  DOI：

  10.1021/ja962126v

文献信息

• MICROORGANISM HAVING MUCIC ACID-PRODUCING ABILITY, AND METHODS FOR PRODUCING MUCIC ACID, 2,5-FURANDICARBOXYLIC ACID, AND 2,5-FURANDICARBOXYLIC ACID DIESTER
  申请人：Mitsubishi Chemical Corporation

  公开号：EP3486323A1

  公开（公告）日：2019-05-22

  A method for efficiently producing mucic acid from a common organic raw material such as glucose or galactose is provided. A method for producing mucic acid, including: using glucose or galactose as a starting material or an intermediate; and obtaining mucic acid via UDP-galacturonic acid and galacturonic acid, which are produced sequentially as intermediates. A microorganism modified to have enhanced UDP-galacturonate pyrophosphorylase activity and to have at least one enhanced enzyme activity selected from the group consisting of UDP-glucuronate 4-epimerase activity, UDP-galactose 6-dehydrogenase activity, and galacturonate dehydrogenase activity, as compared to non-modified strains.

  本发明提供了一种利用葡萄糖或半乳糖等常见有机原料高效生产粘液酸的方法。一种生产粘液酸的方法，包括：使用葡萄糖或半乳糖作为起始原料或中间体；通过作为中间体依次产生的 UDP-半乳糖醛酸和半乳糖醛酸获得粘液酸。一种经改良的微生物，与未改良菌株相比，具有增强的 UDP-半乳糖醛酸焦磷酸化酶活性，并具有至少一种增强的酶活性，这些酶活性选自由 UDP-葡萄糖醛酸 4-酰亚胺酶活性、UDP-半乳糖 6-脱氢酶活性和半乳糖醛酸脱氢酶活性组成的组。
• COMPOSITIONS AND METHODS FOR PRODUCING CHEMICALS AND DERIVATIVES THEREOF
  申请人：Synthetic Genomics, Inc.

  公开号：US20140206047A1

  公开（公告）日：2014-07-24

  The present invention provides methods for producing a product of one or more enzymatic pathways. The pathways used in the methods of the invention involve one or more conversion steps such as, for example, an enzymatic conversion of guluronic acid into D-glucarate (Step 7); an enzymatic conversion of 5-ketogluconate (5-KGA) into L-Iduronic acid (Step 15); an enzymatic conversion of L-Iduronic acid into Idaric acid Step 7b); and an enzymatic conversion of 5-ketocluconate into 4,6-dihydroxy 2,5-diketo hexanoate (2,5-DDH) (Step 16). In some embodiments the methods of the invention produce 2,5-furandicarboxylic acid (FDCA) as a product. The methods include both enzymatic and chemical conversions as steps. Various pathways are also provided for converting glucose into 5-dehdyro-4-deoxy-glucarate (DDG), and for converting glucose into 2,5-furandicarboxylic acid (FDCA). The methods also involve the use of engineered enzymes that perform reactions with high specificity and efficiency. Additional products that can be produce include metabolic products such as, but not limited to, guluronic acid, L-iduronic acid, idaric acid, glucaric acid. Any of the products can be produced using glucose as a substrate or using any intermediate in any of the methods or pathways of the invention.
• BIOSYNTHETIC PATHWAYS AND METHODS
  申请人：REGENTS OF THE UNIVERSITY OF MINNESOTA

  公开号：US20150337342A1

  公开（公告）日：2015-11-26

  This disclosure describes a recombinant microbial cells and methods of making and using such recombinant microbial cells. Generally, the recombinant cells may be modified to exhibit increased biosynthesis of a TCA derivative compared to a wild-type control. In some embodiments, the TCA derivative can include 1,4-butanediol. In various embodiments, the microbial cell is a fungal cell or a bacterial cell. In some embodiments, the increased biosynthesis of the TCA derivative can include an increase in xylose dehydrogenase activity, xylonolactonase activity, xylonate dehydratase activity, or 2-keto-3-deoxyaldonic acid dehydratase activity.
• Use of Halogens in the Production of 2,5-Furandicarboxylic Acid
  申请人：BP Corporation North America Inc.

  公开号：US20170253571A1

  公开（公告）日：2017-09-07

  Methods for providing effective, efficient and convenient ways of producing 2,5-furandicarboxylic acid, are presented, in addition, compositions of 2,5-furandicarboxylic acid including 2;5-furandicarboxylic acid and at least one byproduct are presented. In some aspects, 4-deoxy-5-dehydroglucaric acid is dehydrated to obtain the 2,5-furandicarboxylic acid, A solvent catalyst and/or reactant may be combined with the 4-deoxy-5-dehydroglucaric acid to produce a reaction product including the 2,5-furandicarboxylic acid. In some arrangements, the reaction product may additionally include water and/or byproducts.
• USE OF BROMINE IONS IN THE PRODUCTION OF 2,5-FURANDICARBOXYLIC ACID
  申请人：BP Corporation North America Inc.

  公开号：US20170253573A1

  公开（公告）日：2017-09-07

  Methods for providing effective, efficient and convenient ways of producing 2,5-furandicarboxylic acid are presented. In addition, compositions of 2,5-furandicarboxylic acid including 2,5-furandicarboxylic acid and at least one byproduct are presented. In some aspects, 4-deoxy-5-dehydroglucaric acid is dehydrated to obtain the 2,5-furandicarboxylic acid. A solvent, catalyst, and/or reactant may be combined with the 4-deoxy-5-dehydroglucaric acid to produce a reaction product including the 2,5-furandicarboxylic acid. In some arrangements, the reaction product may additionally include water and/or byproducts.