(3S,4S)-3,4,6-三羟基-2,5-二氧代己酸 | 2595-33-7

• 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: (3S,4S)-3,4,6-三羟基-2,5-二氧代己酸
• 英文名称: 2,5-diketo-D-gluconic acid
• 英文别名: D-threo-[2,5]hexodiulosonic acid；D-threo-[2,5]Hexodiulosonsaeure；2,5-dioxo-D-gluconic acid；2,5-didehydro-D-gluconic acid；(3S,4S)-3,4,6-trihydroxy-2,5-dioxohexanoic acid
• CAS: 2595-33-7
• 化学式: C₆H₈O₇
• 分子量: 192.125
• InChiKey: RXMWXENJQAINCC-DMTCNVIQSA-N

物化性质

• 沸点：
  506.6±50.0 °C(Predicted)
• 密度：
  1.751±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 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

安全信息

• 海关编码：
  2918990090

反应信息

• 作为反应物：
  描述：

  (3S,4S)-3,4,6-三羟基-2,5-二氧代己酸 在 2,5-diketo-D-gluconic acid reductase 、 烟酰胺腺嘌呤双核苷酸磷酸盐 作用下， 以 aq. acetate buffer 为溶剂， 生成 2-酮-L-古洛糖酸
  参考文献：
  名称：

  2,5-Diketo-gluconic acid reductase from Corynebacterium glutamicum: Characterization of stability, catalytic properties and inhibition mechanism for use in vitamin C synthesis

  摘要：

  2,5-Diketo-D-gluconic acid (2,5-DKG) reductase is an NADPH-dependent, monomeric aldo-keto reductase (AKR) which catalyzes the reduction of 2,5-DKG to 2-keto-L-gulonic acid (2-KLG) - the immediate precursor of vitamin C. The reaction catalyzed by 2,5-DKG reductase is attractive to bypass several chemical steps and produce vitamin C biocatalytically. In a screening of 22 bacterial strains, nine 2,5-DKG reductase producing bacterial strains were found. The gene of Corynebacterium glutamicum 2,5-DKG reductase was cloned and overexpressed in Escherichia coli. By batch fermentation 409 mg L-1 of 2,5-DKG reductase with a C-terminal His(6)-tag were obtained. The purified 2,5-DKG reductase was characterized in detail. The enzyme is most active in a pH range from 5.0 to 8.0 and its stability is high at temperatures below 35 degrees C. Catalytic constants for 2,5-DKG and NADPH were determined and a weak inhibition by the product 2-KLG was found. 2,5-DKG reductase activity is strongly inhibited by the common process ions Mg2+, Ca2+, SO43- and Cl-, which suggests that these should be avoided in the process. The inhibition mechanism for Cl- was elucidated. It is a competitive inhibitor with respect to NADPH and a noncompetitive inhibitior with respect to 2,5-DKG. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.procbio.2012.07.014
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 enzymes from acetobacter melanogenum 作用下， 生成 (3S,4S)-3,4,6-三羟基-2,5-二氧代己酸
  参考文献：
  名称：

  Katznelson et al., Journal of Biological Chemistry, 1953, vol. 204, p. 43,50

  摘要：

  DOI：

文献信息

• METHOD FOR PRODUCING ASCORBIC ACID INTERMEDIATES
  申请人：——

  公开号：US20020177198A1

  公开（公告）日：2002-11-28

  The present invention relates to non-fermentative methods for the production of ASA intermediates, KDG, DKG and KLG and methods for the regeneration of co-factor. The invention provides genetically engineered host cells comprising heterologous nucleic acid encoding enzymes useful in the process.

  本发明涉及非发酵方法用于生产ASA中间体，KDG，DKG和KLG以及辅因子再生方法。该发明提供了包含异源核酸编码酶的基因工程宿主细胞，这些酶在该过程中非常有用。
• Fermentation process for converting L-gulonic acid to 2-keto-L-gulonic
  申请人：Pfizer Inc.

  公开号：US04155812A1

  公开（公告）日：1979-05-22

  L-gulonic acid as the calcium or sodium salt is converted to 2-keto-L-gulonate in high yield by means of a growing culture of selected strains of species of the genus Xanthomonas.

  L-古洛酸作为钙盐或钠盐，通过选择属于黄单胞菌属的某些菌种的生长培养物，高产地转化为2-酮基L-古洛酸。
• Destruction by fermentation of 2-ketogluconate in the presence of
  申请人：Pfizer Inc.

  公开号：US04202942A1

  公开（公告）日：1980-05-13

  2-Ketogluconate present in a mixture with 2-ketogulonate is destroyed by fermentation with a strain of a Pseudomonas species leaving desired 2-ketogulonate intact. Subsequent hydrolysis of the 2-ketogulonate yields ascorbic acid.

  一种假单胞菌菌株的发酵可以破坏与2-酮戊糖酸混合物中存在的2-酮葡萄糖酸，使得所需的2-酮葡萄糖酸得以保留。随后对2-酮葡萄糖酸进行水解，可以得到抗坏血酸。
• Process for preparing 2-keto-L-gulonic acid
  申请人：Shionogi & Co., Ltd.

  公开号：US03998697A1

  公开（公告）日：1976-12-21

  2-Keto-L-gulonic acid is prepared directly from D-glucose by microbial conversion utilizing mixed culturing on or mixed contacting with a medium containing D-glucose, employing at least two kind of microorganisms; 2,5-diketo-D-gluconic acid producing strains which belong to the genera of Acetobacter, Acetomonas and Gluconobacter and strains capable of converting the 2,5-diketo-D-gluconic acid into 2-keto-L-gulonic acid which belong to the general of Brevibacterium and Corynebacterium. Both the incubation of the microorganisms in a medium containing D-glucose and the direct contact of any products obtained from the cells of the microorganisms with the substrate may be used in the disclosed process. By-production of the undesired optical isomer, 2-keto-D-gluconic acid, of the intended product is effectively prevented by employing the mixed culturing or contacting because of the presence of the 2,5-diketo-D-gluconic acid producing strain or any products thereof in the medium during at least part of the entire process.

  2-酮-L-古洛酸是通过利用混合培养或混合接触含有D-葡萄糖的培养基，利用至少两种微生物进行微生物转化直接从D-葡萄糖制备而成的；这两种微生物分别为能够产生2,5-二酮-D-葡萄糖酸的Acetobacter、Acetomonas和Gluconobacter属的菌株，以及能够将2,5-二酮-D-葡萄糖酸转化为2-酮-L-古洛酸的Brevibacterium和Corynebacterium属的菌株。在所披露的过程中，可以使用微生物在含有D-葡萄糖的培养基中的孵育，也可以使用从微生物细胞中获得的任何产物与底物直接接触。通过采用混合培养或接触，由于2,5-二酮-D-葡萄糖酸产生菌株或其任何产物在整个过程的至少一部分时间内存在于培养基中，因此可以有效地防止所期望的产物的非期望光学异构体2-酮-D-葡萄糖酸的副产生。
• Method for producing ascorbic acid intermediates
  申请人：Boston Grant Matthew

  公开号：US20050227337A1

  公开（公告）日：2005-10-13

  The present invention relates to non-fermentative methods for the production of ASA intermediates, KDG, DKG and KLG and methods for the regeneration of co-factor. The invention provides genetically engineered host cells comprising heterologous nucleic acid encoding enzymes useful in the process.

  本发明涉及非发酵方法生产ASA中间体，KDG，DKG和KLG以及再生辅因子的方法。该发明提供了包含异源核酸编码酶的基因工程宿主细胞，用于该过程。