β-氟丙酮酸钠盐 | 2923-22-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 中文名称: β-氟丙酮酸钠盐
• 英文名称: sodium 3-fluoropyruvate
• 英文别名: sodium fluoropyruvate；β-fluoropyruvic acid sodium salt；3-fluoropyruvic acid sodium salt；sodium 3-fluoro-2-oxopropanoate；Sodium 3-fluoropyruvate monohydrate；sodium;3-fluoro-2-oxopropanoate
• CAS: 2923-22-0
• 化学式: C₃H₂FO₃*Na
• 分子量: 128.035
• InChiKey: YEXRRCHQJDSEJI-UHFFFAOYSA-M

物化性质

• 熔点：
  145°C
• 稳定性/保质期：
  如果按照规格使用和储存，则不会分解，未有已知危险发生。

计算性质

• 辛醇/水分配系数(LogP)：
  -4.72
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2918300090
• 储存条件：
  -20°C时应密闭存于阴凉干燥处保存。

反应信息

• 作为反应物：
  描述：

  β-氟丙酮酸钠盐 在 重水 作用下， 生成
  参考文献：
  名称：

  The Linkage of Catalysis and Regulation in Enzyme Action. Fluoropyruvate as a Probe of Regulation in Pyruvate Decarboxylases

  摘要：

  Pyruvate decarboxylase, a thiamin-diphosphate (ThDP) dependent enzyme from the yeast Saccharomyces cerevisiae (SCPDC), catalyzes the conversion of fluoropyruvate to carbon dioxide, fluoride ion and acetate ion, as earlier reported for the wheat-germ enzyme (Gish, G.; Smyth, T.; Kluger, R. J. Am. Chem. Sec. 1988, 110, 6230-6234). While the fluoropyruvate reaction with the wheat-germ enzyme does not display the sigmoidal kinetics associated with hysteretic regulation by substrate that pyruvate as substrate produces with the wheat-germ enzyme, this feature and the induction period characteristic of hysteretic regulation are preserved when fluoropyruvate acts as substrate and regulator for SCPDC. The C-1-C-13 kinetic isotope effect for fluoropyruvate with SCPDC is the same as that for pyruvate (1.008-1.009), indicating the decarboxylation step to be about 15% rate limiting in the substrate-binding/decarboxylation part of the reaction. Solvent isotope effects and proton inventories are consistent with the view that fluoropyruvate regulation in SCPDC is not associated with an intracatalytic opening/closing of the active site coupled to sulfhydryl addition of cysteine-221 to the regulator keto group, as is thought to occur in pyruvate regulation of SCPDC. Product-release events in the first few catalytic cycles of the fluoropyruvate reaction, involving enzyme-catalyzed hydrolysis of acetyl-ThDP and release of acetate ion, may bring the wheat-germ enzyme into an ordinarily kinetically inaccessible enzyme-conformational regime analogous to the active form of the bacterial enzyme from Zymomonas mobilis, where the active site is permanently open without occupation of the regulatory site. Binding of fluoropyruvate at the regulatory site of SCPDC, in contrast, may remain necessary in the steady state for active-enzyme function but the active site may be permanently opened, thus not requiring the intracatalytic addition-elimination reactions at the regulatory site.

  DOI：

  10.1021/ja963259j

文献信息

• [EN] BIARYL KINASE INHIBITORS<br/>[FR] INHIBITEURS DE KINASES À BASE DE BIARYLE
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2017059085A1

  公开（公告）日：2017-04-06

  The present disclosure is directed to biaryl compounds of formula (I) which can inhibit AAKl (adaptor associated kinase 1), compositions comprising such compounds and their use for treating e.g. pain, Alzheimer's disease, Parkinson's disease and schizophrenia.

  本公开涉及式(I)的双芳基化合物，该化合物能够抑制AAK1（适配器相关激酶1），包含此类化合物的组合物以及它们用于治疗例如疼痛、阿尔茨海默病、帕金森病和精神分裂症。
• 9-Azido-9-deoxy-2,3-difluorosialic Acid as a Subnanomolar Inhibitor against Bacterial Sialidases
  作者：Wanqing Li、Abhishek Santra、Hai Yu、Teri J. Slack、Musleh M. Muthana、Dashuang Shi、Yang Liu、Xi Chen

  DOI：10.1021/acs.joc.9b00385

  日期：2019.6.7

  several bacterial sialidases and a recombinant human cytosolic sialidase hNEU2 indicated that sialidase inhibition was affected by the C-3 fluorine stereochemistry and derivatization at C-5 and/or C-9 of the inhibitor. Opposite to that observed for influenza A virus sialidases and hNEU2, compounds with axial fluorine at C-3 were better inhibitors (up to 100-fold) against bacterial sialidases compared to

  化学合成了2（a），3（a / e）-二氟唾液酸及其C-5和/或C-9衍生物的文库。多杀巴斯德氏菌唾液酸醛缩酶（PmAldolase），但不包括其大肠杆菌同源物（EcAldolase），被发现催化3-氟（a）-唾液酸的C5-叠氮基类似物的形成。相比之下，尽管PmAldolase通常更有效，但PmAldolase和EcAldolase均可催化3-氟（a / e）-唾液酸及其C-9类似物的合成。化学合成的3-氟（a / e）-唾液酸类似物经过纯化和化学衍生，以形成所需的二氟唾液酸及其衍生物。对几种细菌唾液酸酶和重组人胞浆唾液酸酶hNEU2的抑制研究表明，唾液酸酶的抑制作用受C-3氟立体化学和抑制剂在C-5和/或C-9处的衍生作用的影响。与观察到的甲型流感病毒唾液酸酶和hNEU2相反，与3F赤道对应物相比，在C-3处具有轴向氟的化合物是更好的细菌唾液酸酶抑制剂（最多100倍）。C-5修饰的化合物
• [EN] CELL-PERMEABLE PROBES FOR IDENTIFICATION AND IMAGING OF SIALIDASES<br/>[FR] SONDES PERMÉABLES AUX CELLULES POUR L'IDENTIFICATION ET L'IMAGERIE DE SIALIDASES
  申请人：ACADEMIA SINICA

  公开号：WO2014031498A1

  公开（公告）日：2014-02-27

  Provided herein are novel irreversible sialidase inhibitors. These compounds can be conjugated with a detectable tagging moiety such as azide-annexed biotin via CuAAC for isolation and identification of sialidases. The provided compounds and the corresponding detectable conjugates are useful for detecting sialidase-containing pathogens and imaging in situ sialidase activities under physiological conditions.

  提供了一种新型的不可逆唾液酸酶抑制剂。这些化合物可以通过点击化学（CuAAC）与可检测的标记基团（如叠氮基连在生物素上）进行偶联，用于分离和识别唾液酸酶。所提供的化合物及相应的可检测偶联物可用于检测含有唾液酸酶的病原体，以及在生理条件下对唾液酸酶活性进行成像。
• Sustainable and Continuous Synthesis of Enantiopure<scp>l</scp>-Amino Acids by Using a Versatile Immobilised Multienzyme System
  作者：Susana Velasco-Lozano、Eunice S. da Silva、Jordi Llop、Fernando López-Gallego

  DOI：10.1002/cbic.201700493

  日期：2018.2.16

  Don't move! The synthesis of l‐amino acids is catalysed by a hierarchical, multifunctional, heterogeneous biocatalyst. The hierarchical architecture irreversibly co‐immobilises l‐alanine dehydrogenase from B. subtilis (l‐AlaDH‐Bs) and formate dehydrogenase from C. boidinii (FDH‐Cb), with polyethyleneimine on porous agarose beads. The two enzymes and polymer colocalise across the whole microstructure

  别动！l-氨基酸的合成是由一种分层的，多功能的，非均质的生物催化剂催化的。的分层结构不可逆地共同固定不动升丙氨酸脱氢酶从枯草芽孢杆菌（升-AlaDH-BS）和甲酸脱氢酶从C.博伊丁假丝酵母（FDH-CB）中，用在多孔琼脂糖珠聚乙烯亚胺。两种酶和聚合物在多孔载体的整个微观结构中共定位。
• An Enantio- and Diastereoselective Chemoenzymatic Synthesis of α-Fluoro β-Hydroxy Carboxylic Esters
  作者：James K. Howard、Marion Müller、Alan Berry、Adam Nelson

  DOI：10.1002/anie.201602852

  日期：2016.6.1

  hydrogen peroxide yields the corresponding syn-configured α-fluoro β-hydroxy carboxylic acids which have >98 % ee. The overall chemoenzymatic approach, in which fluoropyruvate serves as a fluoroacetate equivalent, may be exploited in the synthesis of polar building blocks and fragments with potential value in drug discovery.

  氟丙酮酸与许多（杂）芳族醛之间的反式-邻羟基苄基丙酮酸醛缩酶醛缩酶催化的反应产生醛醇加合物而没有随后的脱水。用过氧化氢处理反应产物产生相应的同构构型的α-氟代β-羟基羧酸，其ee> 98％。氟丙酮酸盐相当于氟乙酸盐等同物的整体化学酶学方法可用于极性构建基和片段的合成，在药物发现中具有潜在价值。