aldehydo-D-galacturonate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: aldehydo-D-galacturonate
• 英文别名: (2S,3R,4S,5R)-2,3,4,5-tetrahydroxy-6-oxohexanoate
• 化学式: C6H9O7-
• 分子量: 193.13
• InChiKey: IAJILQKETJEXLJ-RSJOWCBRSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  138
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  aldehydo-D-galacturonate 生成 D-tagaturonate
  参考文献：
  名称：

  KILGORE W.W.; STARR M.P., J Biol Chem, 1959, 0021-9258, 2227-35

  摘要：

  DOI：
• 作为产物：
  描述：

  L-Galactonate 、 NADP⁺ 生成 aldehydo-D-galacturonate 、 氢(+1)阳离子 、 NADPH(4-)
  参考文献：
  名称：

  Engineering increased vitamin C levels in plants by overexpression of a D-galacturonic acid reductase

  摘要：

  水果和蔬菜中的L-抗坏血酸（维生素C）是人体营养的重要组成部分。令人惊讶的是，关于植物中生物合成途径的信息非常有限。在这里，我们报告了草莓基因GalUR的分离和表征，该基因编码一种依赖NADPH的D-半乳糖醛酸还原酶。我们提供了草莓果实中L-抗坏血酸的生物合成是通过D-半乳糖醛酸（细胞壁果胶的主要成分）进行的证据。GalUR的表达与成熟过程中草莓果实中抗坏血酸含量的变化以及不同种草莓果实中抗坏血酸含量的变化有关。转基因草莓果实中果胶酶基因的表达降低导致细胞壁中果胶溶解度降低，从而降低了抗坏血酸含量。拟南芥中GalUR的过度表达使维生素C含量提高了两到三倍，这表明利用该基因提高植物中维生素C含量的工程化是可行的。

  DOI：

  10.1038/nbt777

文献信息

• An evolutionary conserved d-galacturonic acid metabolic pathway operates across filamentous fungi capable of pectin degradation
  作者：Elena S. Martens-Uzunova、Peter J. Schaap

  DOI：10.1016/j.fgb.2008.08.002

  日期：2008.11

  galacturonic acid media identified a highly correlating cluster of four strongly induced hypothetical genes linked with a subset set of genes encoding pectin degrading enzymes. Three of the encoded hypothetical proteins now designated GAAA to GAAC are directly involved in further galacturonic acid catabolism. Functional and biochemical analysis revealed that GAAA is a novel d-galacturonic acid reductase

  在半乳糖醛酸培养基上生长的黑曲霉转移培养物的转录组分析确定了四个相关性强的假想基因的高度相关簇，这些假想基因与编码果胶降解酶的基因子集相连。现在称为GAAC的GAAA编码的三种假设蛋白质直接参与了进一步的半乳糖醛酸分解代谢。功能和生化分析表明，GAAA是一种新型的d-半乳糖醛酸还原酶。不能利用半乳糖醛酸的两个非等位构巢曲霉菌株分别在gAAAhref=https://www.molaid.com/MS_77903 target="_blank">AAA和gAAB的直系同源物中突变。黑曲霉gAAAhref=https://www.molaid.com/MS_77903 target="_blank">AAA和gAAC基因共享一个共同的启动子区域。该特征似乎在来自Pezizomycotina亚门的植物细胞壁降解真菌的基因组中严格保守。
• Vitamin C booster
  作者：Nicholas Smirnoff

  DOI：10.1038/nbt0203-134

  日期：2003.2

  Identification and manipulation of a new enzyme from strawberry demonstrates the feasibility of engineering vitamin C synthesis in plants.

  草莓中一种新酶的鉴定和操作证明了在植物中进行维生素 C 合成工程的可行性。
• Identification in the Mold <i>Hypocrea jecorina </i>of the First Fungal <scp>d</scp>-Galacturonic Acid Reductase
  作者：Satu Kuorelahti、Nisse Kalkkinen、Merja Penttilä、John Londesborough、Peter Richard

  DOI：10.1021/bi050792f

  日期：2005.8.1

  A D-galacturonic acid reductase and the corresponding gene were identified from the mold Hypocrea jecorina (Trichoderma reesei). We hypothesize that the enzyme is part of a fungal D-galacturonic acid catabolic pathway which has not been described previously and which is distinctly different from the bacterial pathway. H. jecorina grown on D-galacturonic acid exhibits an NADPH-dependent D-galacturonic acid reductase activity. This activity is absent when the mold is grown on other carbon sources. The D-galacturonic acid reductase was purified, and tryptic digests of the purified protein were sequenced. The open reading frame of the corresponding gene was then cloned from a cDNA library. The open reading frame was functionally expressed in the yeast Saccharomyces cerevisiae. A histidine-tagged protein was purified, and the enzyme kinetics were characterized. The enzyme converts in a reversible reaction from D-galacturonic acid and NADPH to L-galactonic acid and NADP. The enzyme also exhibits activity with D-glucuronic acid and DL-glyceraldehyde.
• Biological synthesis of ascorbic acid: the conversion of derivatives of <scp>d</scp>-galacturonic acid into <scp>l</scp>-ascorbic acid by plant extracts
  作者：L. W. Mapson、F. A. Isherwood

  DOI：10.1042/bj0640013

  日期：1956.9.1