(2S)-<2-(2)H>-succinic acid | 10013-03-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S)-<2-(2)H>-succinic acid
• 英文别名: (S)-[2H1]succinic acid；(S)-2-deuterio-succinic acid；(2s)Deuteriosuccinic acid；(2S)-2-deuteriobutanedioic acid
• CAS: 10013-03-3
• 化学式: C₄H₆O₄
• 分子量: 119.081
• InChiKey: KDYFGRWQOYBRFD-YUYPMLDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 双氧水 、 溶剂黄146 作用下， 生成 (2S)-<2-(2)H>-succinic acid
  参考文献：
  名称：

  The Contribution of the Substrate's Carboxylate Group to the Mechanism of 4-Oxalocrotonate Tautomerase

  摘要：

  4-Oxalocrotonate tautomerase (4-OT) converts 2-oxo-4E-hexenedioate (1) to 2-oxo-3E-hexenedioate (3) through the dienol intermediate, 2-hydroxy-2,4-hexadiene-1,6-dioate (2). Previous studies established that the isomerization of 1 to 3 is primarily a suprafacial process. It was also suggested that the 6-carboxylate group of the substrate maintains the regio- and stereochemical fidelity of the reaction by anchoring the substrate at the active site. A subsequent study suggested an additional role for the 6-carboxylate group in the mechanism: the enzyme may utilize the binding energy of the carboxylate group to facilitate catalysis. In order to explore the role of the carboxylate group in the mechanism further, the nonenzymatic rate constants for mono- and dicarboxylated substrates were measured and compared to the rates obtained for the corresponding enzymatic reactions. The results show that the missing carboxylate group has a profound effect on enzymatic catalysis as evidenced by the significant decreases (a 10(4)- and a 10(5)-fold reduction) in the values of k(cat)/K-m observed for the two monocarboxylated substrates. A comparison of the nonenzymatic rate constants indicates that the reduced k(cat)/K-m values cannot be explained on the basis of the chemical reactivities. The stereochemical course of the 4-OT-catalyzed reaction was also determined using 2-hydroxy-2,4Z-heptadiene-1,7-dioate. The stereochemical analysis reveals that the presence of the carboxylate group improves the stereoselectivity of the enzyme-catalyzed ketonization of 2-hydroxy-2,4Z-heptadiene-1,7-dioate to 2-oxo-[3-H-2]-4Z-heptene-1,7-dioate in (H2O)-H-2-a result that is consistent with its previously assigned role. These findings provide further evidence that the substrate's carboxylate group contributes to the mechanism of the enzyme in two ways: it anchors the substrate at the active site and it facilitates catalysis by destabilizing the substrate or by stabilizing the transition state. (C) 1998 Academic Press.

  DOI：

  10.1006/bioo.1998.1095

文献信息

• Stereochemical Studies on Homoterpene Biosynthesis in Higher Plants; Mechanistic, Phylogenetic, and Ecological Aspects
  作者：Andreas Gäbler、Wilhelm Boland、Ute Preiss、Helmut Simon

  DOI：10.1002/hlca.19910740820

  日期：1991.12.11

  examined plant families (Agavaceae, Asclepiadaceae, Asteraceae, Leguminosae, Magnoliaceae, and Saxifragaceae). The enzyme tolerates a wide range of structural modifications at the polar head of 3. Instead of 3, also gcranylacclone 12 and the secondary alcohol 13 can be cleaved to the homoterpene 1 and as yet unidentified carbonyl fragments. The CC bonds within the aliphatic chain of 3 seem to be essential

  在高等植物中，两个高同萜烯4,8-二甲基壬基-1,3,7-三烯（1）和4,8,12-三甲基三苯胺-1,3,7,11-teiracnc（2）来源于nerolidol （3）。或香叶菊醇（4）通过其C-骨架离子的氧化裂解而形成。反应进行时，H 8 -C（5）的3完全丢失，并正式生成C 4片段。酶的位点特异性对于迄今检查过的所有植物科（龙舌兰科，萝摩科，菊科，豆科，木兰科和虎耳草科）都是相同的。该酶在3的极性头上可耐受多种结构修饰。gcranylacclone代替312和仲醇13可以裂解为高萜1和尚未鉴定的羰基片段。脂族链3中的CC键似乎对于氧化键裂解以及底物的识别和嵌入酶的活性中心至关重要。饲料诱导的利马豆菜豆叶螨（Tetranychus urticae）感染的利马豆菜豆叶片中1和2的生物合成可能需要事先释放nerolidol（3）或geranyllinalool（4）在断裂反应之前从系统发生
• Stereochemistry of pyrrolizidine alkaloid biosynthesis: incorporation of chiral [2-2H]putrescines into retrorsine
  作者：Ellen K. Kunec、David J. Robins

  DOI：10.1039/c39850001450

  日期：——

  Feeding experiments with (2R)- and (2S)-[2-2H]putrescine on Senecio isatideus plants have shown that hydroxylation at C-7 of retronecine proceeds with retention of configuration and formation of the 1,2-double bond involves removal of the pro-S hydrogen and retention of the pro-R hydrogen at C-2 of retronecine.

  千里光（Senecio isatideus）植物的（2 R）-和（2 S）-[2- 2 H]地屈菜碱的饲喂实验表明，逆转录素C-7处的羟基化作用可保持构型和1,2-双键的形成包括除去的亲-小号氢和保留亲- - [R在C-2 retronecine的氢。
• The Complete Stereochemistry of the Enzymatic Dehydration of 4-Hydroxybutyryl Coenzyme A to Crotonyl Coenzyme A
  作者：Peter Friedrich、Daniel J. Darley、Bernard T. Golding、Wolfgang Buckel

  DOI：10.1002/anie.200705473

  日期：2008.4.14
• Elucidation of stereospecificity of a selenium-containing hydrogenase from methanococcus vannielii — syntheses of (R)- and (S)-[4-2H1] 3,4-dihydro-7-hydroxy-1-hydroxyethylquinolinone
  作者：Tadashi Teshima、Akira Nakaji、Tetsuo Shiba、Lin Tsai、Shigeko Yamazaki

  DOI：10.1016/s0040-4039(01)80815-7

  日期：——