(2S,3S)-2-deuterio-3-hydroxy-succinic acid | 3038-37-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (2S,3S)-2-deuterio-3-hydroxy-succinic acid
• 英文别名: (2S,3R)-<3-(2)H1>malic acid；(2R,3R)-<3-2H>-malic acid；(2R,3R/2S,3S)-<3-2H>-malic acid；Threo-3-Deutero-D,L-aepfelsaeure；(2RS,3RS)-2-deuterio-3-hydroxy-succinic acid；DL-threo-3-deuterio-malic acid；(+/-)-threo-2-Deuterio-3-hydroxy-bernsteinsaeure；DL-threo-3-Deuterio-aepfelsaeure；(2R,3R)-3-deuteriomalic acid；L_g-threo-3-deuterio-malic acid；L_g-threo-2-Deuterio-3-hydroxy-bernsteinsaeure；L_g-threo-3-Deuterio-aepfelsaeure；(2R,3R)-2-Deuterio-3-hydroxy-bernsteinsaeure
• CAS: 3038-37-7；17429-14-0；74804-16-3；90587-17-0
• 化学式: C₄H₆O₅
• 分子量: 135.081
• InChiKey: BJEPYKJPYRNKOW-SLBLOSDKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.09
• 重原子数：
  9.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  94.83
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2S,3S)-2-deuterio-3-hydroxy-succinic acid 在 Na₂HPO₄ buffer 、 magnesium chloride 作用下， 生成 (2R,3S)-<3-2H>-malic acid
  参考文献：
  名称：

  4-草酰巴豆酸互变异构酶对 2-羟基-2,4-戊二烯酸的酮化作用：对立体化学过程和机制的影响

  摘要：

  4-草酰巴豆酸互变异构酶 (EC 5.3.2-; 4-OT)，一种参与将儿茶酚细菌降解为克雷布斯循环中间体的酶，催化 2-羟基粘康酸 (1) 酮化为 α,β-不饱和酮(E)-2-oxo-3-hexenedioate (2)。对 4-OT 的动力学研究表明，该酶是一种异构酶，通过 1 的中介催化 (E)-2-oxo-4-hexenedioate (3) 转化为 2。异构酶可以通过 «one-base » 或“双基”机制。异构酶反应的整体立体化学过程可用于区分这两种机制。4-OT 反应的立体化学分析存在挑战，因为所提出的底物 3 无法合成或分离

  DOI：

  10.1021/ja00071a007
• 作为产物：
  描述：

  L-erythro-2-bromo-3-deuterio-succinic acid 在 氢氧化钾 作用下， 生成 (2S,3S)-2-deuterio-3-hydroxy-succinic acid
  参考文献：
  名称：

  Cystic Ovarian Metastasis from Papillary Thyroid Carcinoma: A Case Report

  摘要：

  Ovarian metastasis from a primary thyroid carcinoma is rare. In this report we describe a woman who manifested the unusual occurrence of metastases of papillary thyroid carcinoma to the ovary. Both clinically and pathologically, such a presentation can be difficult to distinguish from benign cystic neoplasms of the ovary or cystic struma ovarii.

  DOI：

  10.1089/105072501753271789

文献信息

• Preparation of both enantiomers of malic and citramalic acid and other hydroxysuccinic acid derivatives by stereospecific hydrations of cis or trans 2-butene-1,4-dioic acids with resting cells of Clostridium formicoaceticum
  作者：Richard Eck、Helmut Simon

  DOI：10.1016/s0040-4020(01)85678-7

  日期：1994.1

  (S)-malic, (R)citramalic, (S)-citramalic, (2R,3S)-2-hydroxy-3-methyl-succinic and (2R,3S)-2,3-dimethyl-2-hydroxysuccinic acid were prepared on scales up to 25 mmol by stereospecific addition of water to different 2-butene-1,4-dioic acid derivatives catalyzed by resting cells of Clostridium formicoaceticum (Scheme 1). The (3R)-monodeuterio (R)- and (S)-malic acid as well as (R)- and (S)-citramalic acid were

  （R）-苹果酸，（S）-苹果酸，（R）柠檬酸，（S）-柠檬酸，（2 R，3 S）-2-羟基-3-甲基-琥珀酸和（2 R，3 S）-2通过将水立体定向加成到不同的2-丁烯-1,4-二酸衍生物中，由梭状梭状芽孢杆菌的静止细胞催化，可制备高达25 mmol的规模的3-3-二甲基-2-羟基琥珀酸（方案1）。的（3 - [R）-monodeuterio（[R ）-和（小号） -苹果酸，以及（- [R ）-和（小号）-citramalic苯甲酸用冷冻干燥的细胞中制备的2H 2 O缓冲区。在大多数情况下，产品的立体化学纯度均≥99％。
• Johnson; Hajipour; Whitman, Journal of the American Chemical Society, 1995, vol. 117, # 34, p. 8719 - 8726
  作者：Johnson、Hajipour、Whitman

  DOI：——

  日期：——
• The Contribution of the Substrate's Carboxylate Group to the Mechanism of 4-Oxalocrotonate Tautomerase
  作者：Huiling Lian、Robert M. Czerwinski、Thanuja M. Stanley、William H. Johnson、Robert J. Watson、Christian P. Whitman

  DOI：10.1006/bioo.1998.1095

  日期：1998.10

  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.
• STEREOCHEMISTRY OF THE FUMARASE AND ASPARTASE CATALYZED REACTIONS AND OF THE KREBS CYCLE FROM FUMARIC ACID TO d-ISOCITRIC ACID^1,2
  作者：Oscar Gawron、Thomas P. Fondy

  DOI：10.1021/ja01532a059

  日期：1959.12
• Lian Huiling, Whithman Christian P., J. Amer. Chem. Soc, 115 (1993) N 18, S 7978-7984
  作者：Lian Huiling, Whithman Christian P.

  DOI：——

  日期：——