4-(羟基氨基)-4-氧代丁酸 | 4743-99-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 4-(羟基氨基)-4-氧代丁酸
• 英文名称: N-hydroxysuccinimide
• 英文别名: succinyl hydroxamate；succinomonohydroxamic acid；Succinomonohydroxamsaeure；succinic acid monooxamide；1-Hydroxylamino-1-oxo-3-carboxy-propan；Bernsteinsaeuremonohydroxamat；4-(Hydroxyamino)-4-oxobutanoic acid
• CAS: 4743-99-1
• 化学式: C₄H₇NO₄
• mdl: MFCD01209360
• 分子量: 133.104
• InChiKey: AGEUQNZXCIVHPB-UHFFFAOYSA-N

物化性质

• 熔点：
  82-86 °C(Solv: acetonitrile (75-05-8))
• 密度：
  1.436±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  9
• 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：
  86.6
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  | 2-8°C |

反应信息

• 作为反应物：
  描述：

  4-(羟基氨基)-4-氧代丁酸 在 氨 作用下， 生成 乙酸-N-琥珀酰亚胺酯
  参考文献：
  名称：

  Hantzsch; Urbahn, Chemische Berichte, 1895, vol. 28, p. 760

  摘要：

  DOI：
• 作为产物：
  描述：

  4-(benzyloxyamino)-4-oxobutanoic acid 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以86%的产率得到4-(羟基氨基)-4-氧代丁酸
  参考文献：
  名称：

  Inhibitors of the FEZ-1 metallo-β-lactamase

  摘要：

  Metallo-beta-lactamases (MBLs) catalyze the hydrolysis of beta-lactams including penicillins, cephalosporins and carbapenems. Starting from benzohydroxamic acid (1) structure-activity studies led to the identification of selective inhibitors of the FEZ-1 MBL, e.g., 2,5-substituted benzophenone hydroxamic acid 17 has a K-i of 6.1 +/- 0.71 mu M against the FEZ-1 MBL but does not significantly inhibit the IMP-1, Bell, CphA or L1 MBLs. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.11.053

文献信息

• Reactivity and mechanism of α-nucleophile scaffolds as catalytic organophosphate scavengers
  作者：Pamela T. Wong、Somnath Bhattacharjee、Jayme Cannon、Shengzhuang Tang、Kelly Yang、Sierra Bowden、Victoria Varnau、Jessica J. O'Konek、Seok Ki Choi

  DOI：10.1039/c9ob00503j

  日期：——

  Design and in vitro validation of polar α-nucleophile scaffolds that offer potent catalytic reactivity and practical utility for organophosphate decontamination.

  设计和体外验证极性α-亲核试剂支架，提供强大的催化活性和实际用于有机磷去污的效用。
• Structural Insights into the Catalytic Active Site and Activity of Human Nit2/ω-Amidase
  作者：Chin-Hsiang Chien、Quan-Ze Gao、Arthur J.L. Cooper、Jyun-Hong Lyu、Sheh-Yi Sheu

  DOI：10.1074/jbc.m111.259119

  日期：2012.7

  the methionine salvage pathway. Thus, hNit2/omega-amidase links sulfur metabolism to the tricarboxylic acid cycle. To elucidate the catalytic specificity of hNit2/omega-amidase, we performed molecular dynamics simulations on the wild type enzyme and its mutants to investigate enzyme-substrate interactions. Binding free energies were computed to characterize factors contributing to the substrate specificity

  人类腈水解酶样蛋白 2 (hNit2) 是一种推定的肿瘤抑制因子，最近被鉴定为 omega-酰胺酶。hNit2/omega-酰胺酶通过催化 α-酮戊二酸（谷氨酰胺的 α-酮类似物）和 α-酮琥珀酸（天冬酰胺的 α-酮类似物）的水解，分别产生 α-酮戊二酸和草酰乙酸，发挥重要的代谢作用。谷氨酰胺和 alpha-keto-gamma-methiolbutyrate 之间的转氨作用关闭了蛋氨酸补救途径。因此，hNit2/omega-酰胺酶将硫代谢与三羧酸循环联系起来。为了阐明 hNit2/omega-酰胺酶的催化特异性，我们对野生型酶及其突变体进行了分子动力学模拟，以研究酶-底物相互作用。计算结合自由能以表征促成底物特异性的因素。由这些计算得出的预测得到了动力学分析和突变研究的验证。hNit2/omega-酰胺酶的活性用α-酮戊二酸和琥珀酸作为底物测定。我们构建了三个催化三联体突变体（E43A、K112A
• The synthesis of some N-hydroxyimides
  作者：D. E. Ames、T. F. Grey

  DOI：10.1039/jr9550000631

  日期：——
• 2-Oxoglutarate analogue inhibitors of prolyl hydroxylase domain 2
  作者：Jasmin Mecinović、Christoph Loenarz、Rasheduzzaman Chowdhury、Christopher J. Schofield

  DOI：10.1016/j.bmcl.2009.09.005

  日期：2009.11

  Analogues of the 2-oxoglutarate cosubstrate of the human oxygen sensing enzyme prolyl hydroxylase domain 2 (PHD2) with variations in the potential iron-chelating group were screened as inhibitors and for binding (using non-denaturing electrospray ionization mass spectrometry) to PHD2. (c) 2009 Elsevier Ltd. All rights reserved.
• Rapid Cross-Linking of Proteins by 4-Ketoaldehydes and 4-Hydroxy-2-alkenals Does Not Arise from the Lysine-Derived Monoalkylpyrroles
  作者：Guozhang Xu、Yahua Liu、Mayank M. Kansal、Lawrence M. Sayre

  DOI：10.1021/tx990056a

  日期：1999.9.1

  Exposure of proteins to 4-hydroxy-2-nonenal (HNE) results in conversion of lysines in part to 2-pentylpyrroles that can be formed in higher yield by exposure to the isomeric 4-oxononanal. Since both HNE and 4-oxononanal cause protein cross-linking, and since pyrrolation of proteins by gamma-diketones is also known to result in protein cross-linking, it has been considered that the initially formed 2-pentylpyrroles are responsible for the protein cross-linking seen for HNE and 4-oxononanal. Here we show that protein-bound 2-alkylpyrrole products associated with modification by 4-hydroxy-2-alkenals and 4-oxoalkanals, possessing only monoalkyl substitution, induce undetectable levels of autoxidation-mediated protein cross-linking over time periods where the parent aldehydes effect extensive protein cross-linking, which then must be occurring through alternative mechanisms. Finally, using both RNase and BSA, our finding that reductive methylation of lysines blocks protein cross-linking induced by either HNE or 4-oxononanal (and development of fluorescence in the case of HNE) implicates the obligatory role of lysines in the cross-linking reactions.