8-fluoro-4-methylumbelliferone

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 8-fluoro-4-methylumbelliferone
• 英文别名: 8-Fluoro-7-hydroxy-4-methylcoumarin；8-fluoro-7-hydroxy-4-methylchromen-2-one
• 化学式: C₁₀H₇FO₃
• 分子量: 194.162
• InChiKey: OSVSVMCLEYHROD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-fluoro-4-methylumbelliferone 在 甲醇 、 α-2,6-sialyl transferase 、 四丁基溴化铵 、 sodium methylate 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 3.5h， 生成 (2R,4S,5R,6R)-5-acetamido-2-(((2R,3R,4S,5R,6S)-6-((8-fluoro-4-methyl-2-oxo-2H-chromen-7-yl)oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)methoxy)-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxypropyl)tetrahydro-2H-pyran-2-carboxylic acid
  参考文献：
  名称：

  绿色小单孢菌唾液酸酶催化水解的去糖基化会限制周转率：Michaelis 复合物的构象意义

  摘要：

  基于核心结构 7-(5-acetamido-3,5-dideoxy-d-glycero-α-d-galacto-non-2-ulopyranosylonic acid)-(2→6) 的一组七种同位素取代的唾液酸苷天然底物类似物)-β-D-吡喃半乳糖氧基)-8-氟-4-甲基香豆素 (1, Neu5Acα2,6GalβFMU) 已被合成并用于探测 M. viridifaciens 唾液酸酶转换的限速步骤。环氧 ((18)V)、离去基团氧 ((18)V)、异头碳 ((13)V)、C3-碳 ((13) V)、C3-R 氘 ((D)V(R))、C3-S 氘 ((D)V(S)) 和 C3-双氘 ((D)(2)V) 为 0.986 ± 0.003、1.003分别为 ± 0.005、1.021 ± 0.006、1.001 ± 0.008、1.029 ± 0.007、0.891 ± 0.008 和 0.890

  DOI：

  10.1021/ja109199p
• 作为产物：
  描述：

  2-氟-1,3-二甲氧基-4-硝基苯 在 盐酸 、 palladium 10% on activated carbon 、 氢气 、 三溴化硼 、 sodium nitrite 作用下， 以 甲烷磺酸 、 乙醇 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 11.25h， 生成 8-fluoro-4-methylumbelliferone
  参考文献：
  名称：

  绿色小单孢菌唾液酸酶催化水解的去糖基化会限制周转率：Michaelis 复合物的构象意义

  摘要：

  基于核心结构 7-(5-acetamido-3,5-dideoxy-d-glycero-α-d-galacto-non-2-ulopyranosylonic acid)-(2→6) 的一组七种同位素取代的唾液酸苷天然底物类似物)-β-D-吡喃半乳糖氧基)-8-氟-4-甲基香豆素 (1, Neu5Acα2,6GalβFMU) 已被合成并用于探测 M. viridifaciens 唾液酸酶转换的限速步骤。环氧 ((18)V)、离去基团氧 ((18)V)、异头碳 ((13)V)、C3-碳 ((13) V)、C3-R 氘 ((D)V(R))、C3-S 氘 ((D)V(S)) 和 C3-双氘 ((D)(2)V) 为 0.986 ± 0.003、1.003分别为 ± 0.005、1.021 ± 0.006、1.001 ± 0.008、1.029 ± 0.007、0.891 ± 0.008 和 0.890

  DOI：

  10.1021/ja109199p

文献信息

• [EN] 8-FLUORO-4-ALKYLUMBELLIFERYL ALPHA-D-GLUCOPYRANOSIDE, BIOLOGICAL STERILIZATION INDICATOR INCLUDING THE SAME AND ITS USE IN A METHOD OF DETERMINING EFFICACY OF A STERILIZATION PROCESS<br/>[FR] 8-FLUORO-4-ALKYLUMBELLIFERYL ALPHA-D-GLUCOPYRANOSIDE, INDICATEUR DE STÉRILISATION BIOLOGIQUE LE COMPRENANT ET SON UTILISATION DANS UN PROCÉDÉ DE DÉTERMINATION DE L'EFFICACITÉ D'UN PROCÉDÉ DE STÉRILISATION
  申请人：3M INNOVATIVE PROPERTIES CO

  公开号：WO2021059058A1

  公开（公告）日：2021-04-01

  A self-contained biological sterilization indicator comprises: a housing; bacterial spores comprising, and/or capable of producing, an enzyme capable of catalyzing cleavage of an enzyme substrate; and a frangible container containing a composition, wherein the composition comprises the enzyme substrate, wherein if the frangible container is broken the composition will contact the bacterial spores to form a mixture having an initial pH in the range from 6.0 to 9.0. The enzyme substrate comprises a fluorinated 4'-alkylumbelliferyl α-D-glucopyranoside represented by the structural formula (I), wherein R is an alkyl group having from 1 to 12 carbon atoms. A biological sterilization indicator comprising a kit containing isolated components comprising (i) bacterial spores comprising, and/or capable of producing, an enzyme capable of catalyzing cleavage of the enzyme substrate and a method of assessing efficacy of a sterilization process are also disclosed.

  一个独立的生物灭菌指示器包括：一个外壳；包含细菌孢子的、和/或能够产生能够催化酶底物裂解的酶的细菌孢子；以及一个易碎容器，其中容器内含有一种组合物，该组合物包括酶底物，如果易碎容器破裂，组合物将接触细菌孢子形成具有初始pH在6.0至9.0范围内的混合物。酶底物包括由结构式(I)表示的氟化的4'-烷基炔香豆蔻基α-D-葡萄糖苷，其中R是具有1至12个碳原子的烷基基团。还公开了一种包含孤立组分的套件的生物灭菌指示器，其中组分包括（i）包含细菌孢子的、和/或能够产生能够催化酶底物裂解的酶的细菌孢子，以及一种评估灭菌过程有效性的方法。
• A Mechanistic Study on the Non‐enzymatic Hydrolysis of Kdn Glycosides
  作者：Ali Nejatie、Cinzia Colombo、Benyamin Hakak‐Zargar、Andrew J. Bennet

  DOI：10.1002/ejoc.202101387

  日期：2022.1.27

  neuraminidase activity and selectivity, is shown to increase when the C5-substituent becomes sterically smaller (lower A-value), while electronic effects (Taft values) are less important for these hydrolysis reactions.

  4-硝基苯基唾液酸苷是用于评估神经氨酸酶活性和选择性的底物，当 C5 取代基在空间上变小（较低的 A 值）时，其内在反应性会增加，而电子效应（Taft 值）对这些水解反应。
• Intrinsic Nucleophilicity of Inverting and Retaining Glycoside Hydrolases Revealed Using Carbasugar Glyco-Tools
  作者：Oluwafemi Akintola、Weiwu Ren、Pal John Pal Adabala、Sandeep Bhosale、Yang Wang、Yumeela Ganga-Sah、Robert Britton、Andrew J. Bennet

  DOI：10.1021/acscatal.1c01634

  日期：2021.8.6

  proceeds with little nucleophilic participation by the bound water molecule at the reaction transition state. In contrast, the reaction of carbagalactose substrates with the retaining GH97 enzyme involves a rate-limiting nonchemical step, likely a conformational change, followed by rapid substitution involving a nucleophilic amino acid residue to give a covalently bound intermediate. Considering the structural

  基于环己烯基carbasugars的水解模拟任一α- d葡萄糖或α- d半乳糖具有两个进行了探索多形拟杆菌的酶从糖苷水解酶家族97：反相α葡糖苷酶（Bt基因GH97a）和保持α半乳糖苷酶（Bt基因GH97b)。两种酶都在碳糖底物的假异头中心产生亲核取代，为作为离去基团能力函数的催化速率常数提供显着不同的线性能量关系。具体而言，转化α-葡萄糖苷酶的动力学数据与通过反应过渡态结合水分子几乎没有亲核参与的机制产生水解的转化葡糖苷产物的反应一致。相比之下，羧基半乳糖底物与保留的 GH97 酶的反应涉及一个限速非化学步骤，可能是构象变化，然后是涉及亲核氨基酸残基的快速取代，以产生共价结合的中间体。6 ) 独特的酶促亲核试剂之间亲核攻击速率的差异——在转化 α-葡糖苷酶中亲核性较低的物质是 H 2 O，而较好的亲核试剂是保留的 α-半乳糖苷酶中的羧酸盐。苯基碳糖的酶促速率常数比与使用天然底物苯基吡喃糖
• Synthesis of novel fluorinated coumarins: Excellent UV-light excitable fluorescent dyes
  作者：Wei-Chuan Sun、Kyle R Gee、Richard P Haugland

  DOI：10.1016/s0960-894x(98)00578-2

  日期：1998.11

  Two new fluorinated fluorescent dyes, 6,8-difluoro-7-hydroxy-4-methylcoumarin (Marina Blue(TM)) and 3-carboxy-6,8-difluoro-7-hydroxycoumarin (Pacific Blue(TM)), exhibit excellent photophysical properties among a series of novel fluorinated 7-hydroxycoumarins. Most of these fluorinated coumarins have quantum yields (0.63 to 0.89) equal to or higher than that of the parent compound (0.63), which, in combination with their lower pK(a)s and higher photostability, make them superior fluorescent dyes fbr use as reporter molecules in biological systems. (C) 1998 Elsevier Science Ltd. All rights reserved.
• 8-FLUORO-4-ALKYLUMBELLIFERYL ALPHA-D-GLUCOPYRANOSIDE, BIOLOGICAL STERILIZATION INDICATOR INCLUDING THE SAME AND ITS USE IN A METHOD OF DETERMINING EFFICACY OF A STERILIZATION PROCESS
  申请人：3M INNOVATIVE PROPERTIES COMPANY

  公开号：US20220281908A1

  公开（公告）日：2022-09-08

  A self-contained biological sterilization indicator comprises: a housing; bacterial spores comprising, and/or capable of producing, an enzyme capable of catalyzing cleavage of an enzyme substrate; and a frangible container containing a composition, wherein the composition comprises the enzyme substrate, wherein if the frangible container is broken the composition will contact the bacterial spores to form a mixture having an initial pH in the range from 6.0 to 9.0. The enzyme substrate comprises a fluorinated 4′-alkylumbelliferyl α-D-glucopyranoside represented by the structural formula (I), wherein R is an alkyl group having from 1 to 12 carbon atoms. A biological sterilization indicator comprising a kit containing isolated components comprising (i) bacterial spores comprising, and/or capable of producing, an enzyme capable of catalyzing cleavage of the enzyme substrate and a method of assessing efficacy of a sterilization process are also disclosed.