galactaro-1,4-lactone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: galactaro-1,4-lactone
• 英文别名: γ-galactarolactone；D-galactaro-1,4-lactone；DL-galactaric acid-1=>4-lactone；DL-Galactarsaeure-1=>4-lacton；Galactarsaeure-1=>4-lacton；Monolacton der Schleimsaeure；(2R)-2-[(2S,3S,4S)-3,4-dihydroxy-5-oxooxolan-2-yl]-2-hydroxyacetic acid
• 化学式: C₆H₈O₇
• 分子量: 192.125
• InChiKey: XECPAIJNBXCOBO-QDQPNEQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  124
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  苯肼 、 galactaro-1,4-lactone 在 水 作用下， 生成 galactaric acid mono-(N'-phenyl-hydrazide)
  参考文献：
  名称：

  Fischer,E., Chemische Berichte, 1891, vol. 24, p. 2140

  摘要：

  DOI：
• 作为产物：
  描述：

  半乳糖醛酸 在 uronate dehydrogenase from Agrobacterium tumefaciens 、 β-烟酰胺腺嘌呤二核苷酸 作用下， 反应 0.5h， 生成 galactaro-1,4-lactone
  参考文献：
  名称：

  Crystal Structure of Uronate Dehydrogenase from Agrobacterium tumefaciens

  摘要：

  Uronate dehydrogenase from Agrobacterium tumefaciens (AtUdh) belongs to the short-chain dehydrogenase/reductase superfamily and catalyzes the oxidation of D-galacturonic acid and D-glucuronic acid with NAD(+) as a cofactor. We have determined the crystal structures of an apo-form of AtUdh, a ternary form in complex with NADH and product (substrate-soaked structure), and an inactive Y136A mutant in complex with NAD(+). The crystal structures suggest AtUdh to be a homohexamer, which has also been observed to be the major form in solution. The monomer contains a Rossmann fold, essential for nucleotide binding and a common feature of the short-chain dehydrogenase/reductase family enzymes. The ternary complex structure reveals a product, D-galactaro-1,5-lactone, which is bound above the nicotinamide ring. This product rearranges in solution to D-galactaro-1,4-lactone as verified by mass spectrometry analysis, which agrees with our previous NMR study. The crystal structure of the mutant with the catalytic residue Tyr-136 substituted with alanine shows changes in the position of Ile-74 and Ser-75. This probably altered the binding of the nicotinamide end of NAD(+), which was not visible in the electron density map. The structures presented provide novel insights into cofactor and substrate binding and the reaction mechanism of AtUdh. This information can be applied to the design of efficient microbial conversion of D-galacturonic acid-based waste materials.

  DOI：

  10.1074/jbc.m111.254854

文献信息

• Khotinsky; Epifanowa, Bulletin de la Societe Chimique de France, 1925, vol. <4> 37, p. 549
  作者：Khotinsky、Epifanowa

  DOI：——

  日期：——
• Malaguti, Annales de Chimie (Cachan, France), 1835, vol. <2> 60, p. 195
  作者：Malaguti

  DOI：——

  日期：——
• Bergmann, Chemische Berichte, 1921, vol. 54, p. 1362,1375
  作者：Bergmann

  DOI：——

  日期：——
• Sustainable synthesis of zwitterionic galactaric acid monoamides as monomers of hydroxylated polyamides
  作者：Grazia Isa. C. Righetti、Ada Truscello、Jiemeng Li、Roberto Sebastiano、Attilio Citterio、Cristian Gambarotti

  DOI：10.1080/07328303.2022.2105861

  日期：2022.6.13