p-nitrophenyl 2-deoxy-2-trifluoroacetamido-β-D-glucopyranoside | 53439-34-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-nitrophenyl 2-deoxy-2-trifluoroacetamido-β-D-glucopyranoside
• 英文别名: TfaNH(-2d)Glc(b)-O-Ph(4-NO2)；N-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(4-nitrophenoxy)oxan-3-yl]-2,2,2-trifluoroacetamide
• CAS: 53439-34-2
• 化学式: C₁₄H₁₅F₃N₂O₈
• 分子量: 396.277
• InChiKey: ZZOLUQLUKMZKPU-LZQZFOIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  154
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  p-nitrophenyl 2-deoxy-2-trifluoroacetamido-β-D-glucopyranoside 在 三甲基铵三氧化硫共聚物 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以67%的产率得到p-nitrophenyl 2-deoxy-6-O-sulfonate-2-trifluoroacetamido-β-D-glucopyranoside sodium salt
  参考文献：
  名称：

  Design of N-acetyl-6-sulfo-β-d-glucosaminide-based inhibitors of influenza virus sialidase

  摘要：

  Biological activity of N-acetyl-6-SUIfO-beta-D-glucosaminides (6-sulfo-GlcNAc 1) having a structural homology to N-acetylneuraminic acid (Neu5Ac 2) and 2-deoxy-2,3-dehydro-N-acetylneuraminic acid (Neu5Ac2en 3) was examined in terms of inhibitory activity against influenza virus sialidase (influenza, A/Memphis/l/71 H3N2). pNP 6-Sulfo-GlcNAc la was proved to show substantial activity to inhibit the virus sialidaSe IC50 2.8 mM), though p-nitrophenyl (pNP) GlcNAc without 6-sulfo group and pNP 6-sulfo-GlcNH(3)(+) 1b without 2-NHAc showed little activity IC50 > 50 mM). The activity was enhanced nearly 100-fold when the pNP group of la was converted to p-acetamidophenyl one 5 (IC50 = 30 muM) or replaced with 1-naphthyl 6 IC50 = 10 muM) or n-propyl one 8 (IC50 = 11 muM) (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.01.013
• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-2-deoxy-2-trifluoroacetamido-α-D-glucospyranosyl bromide 在 2,6-二甲基吡啶 、 ammonium hydroxide 、 Celite 、 silver carbonate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 8.0h， 生成 p-nitrophenyl 2-deoxy-2-trifluoroacetamido-β-D-glucopyranoside
  参考文献：
  名称：

  β- N-乙酰基己糖胺酶催化N-酰基修饰的底物的水解和转糖基化反应

  摘要：

  35种真菌β- N-乙酰基己糖胺酶与对硝基苯基2-氨基-2-脱氧-β-d-吡喃葡萄糖苷及其4种N-酰基衍生物（CHO，COCH 2 OH，COCH 2 CH 3的水解和转糖基化能力），COCF 3）作为底物进行了测试。的四种新型制备p硝基苯基二糖从由酶催化的这些非天然底物的米曲霉，草酸青霉和踝节菌属菌代表了相当大的扩展糖苷酶的合成潜力。

  DOI：

  10.1016/j.tet.2003.10.111

文献信息

• Probing Synergy between Two Catalytic Strategies in the Glycoside Hydrolase <i>O</i>-GlcNAcase Using Multiple Linear Free Energy Relationships
  作者：Ian R. Greig、Matthew S. Macauley、Ian H. Williams、David J. Vocadlo

  DOI：10.1021/ja904506u

  日期：2009.9.23

  revealing changes in mechanism, transition state, and rate-determining step upon concomitant variation of both nucleophilic strength and leaving group abilities are observed. The observed changes in mechanism reflect the roles played by the enzymic general acid and the catalytic nucleophile. Significantly, these results illustrate how the enzyme synergistically harnesses both modes of catalysis; a feature that

  人类 O-GlcNAcase 在调节丝氨酸和苏氨酸残基与 β-O 连接的 N-乙酰氨基葡萄糖单糖单元 (O-GlcNAc) 的翻译后修饰方面发挥着重要作用。O-GlcNAcase 的机制涉及底物的 2-乙酰氨基基团的亲核参与以取代糖苷连接的离去基团。这种酶对底物结构变化的耐受性使我们能够使用几个系列的底物来表征 O-GlcNAcase 过渡态，以产生多个同时的自由能关系。观察到伴随亲核强度和离去基团能力变化的机制、过渡态和速率决定步骤的变化模式。观察到的机制变化反映了酶通酸和催化亲核试剂所起的作用。重要的是，这些结果说明了酶如何协同利用两种催化模式；许多小分子催化模型都没有的特征。这些研究还表明了氧代碳鎓离子中间体在 O-GlcNAcase 催化的氨基葡萄糖水解中的动力学意义，探索了使用酶过渡态结构的非原子研究可能学到的知识的局限性，并提供了关于保留超家族的一般见解糖苷水解酶作为有效的催化剂。
• Design of N-acetyl-6-sulfo-β-d-glucosaminide-based inhibitors of influenza virus sialidase
  作者：Kenji Sasaki、Yoshihiro Nishida、Mikie Kambara、Hirotaka Uzawa、Tadanobu Takahashi、Takashi Suzuki、Yasuo Suzuki、Kazukiyo Kobayashi

  DOI：10.1016/j.bmc.2004.01.013

  日期：2004.3

  Biological activity of N-acetyl-6-SUIfO-beta-D-glucosaminides (6-sulfo-GlcNAc 1) having a structural homology to N-acetylneuraminic acid (Neu5Ac 2) and 2-deoxy-2,3-dehydro-N-acetylneuraminic acid (Neu5Ac2en 3) was examined in terms of inhibitory activity against influenza virus sialidase (influenza, A/Memphis/l/71 H3N2). pNP 6-Sulfo-GlcNAc la was proved to show substantial activity to inhibit the virus sialidaSe IC50 2.8 mM), though p-nitrophenyl (pNP) GlcNAc without 6-sulfo group and pNP 6-sulfo-GlcNH(3)(+) 1b without 2-NHAc showed little activity IC50 > 50 mM). The activity was enhanced nearly 100-fold when the pNP group of la was converted to p-acetamidophenyl one 5 (IC50 = 30 muM) or replaced with 1-naphthyl 6 IC50 = 10 muM) or n-propyl one 8 (IC50 = 11 muM) (C) 2004 Elsevier Ltd. All rights reserved.
• Hydrolytic and transglycosylation reactions of N-acyl modified substrates catalysed by β-N-acetylhexosaminidases
  作者：Pavla Fialová、Lenka Weignerová、Jana Rauvolfová、Věra Přikrylová、Andrea Pišvejcová、Rüdiger Ettrich、Marek Kuzma、Petr Sedmera、Vladimı́r Křen

  DOI：10.1016/j.tet.2003.10.111

  日期：2004.1

  hydrolytic and transglycosylation capabilities of 35 fungal β-N-acetylhexosaminidases with p-nitrophenyl 2-amino-2-deoxy-β-d-glucopyranoside and its four N-acyl derivatives (CHO, COCH2OH, COCH2CH3, COCF3) as substrates were tested. The preparation of four novel p-nitrophenyl disaccharides from these unnatural substrates catalysed by enzymes from Aspergillus oryzae, Penicillium oxalicum and Talaromyces flavus

  35种真菌β- N-乙酰基己糖胺酶与对硝基苯基2-氨基-2-脱氧-β-d-吡喃葡萄糖苷及其4种N-酰基衍生物（CHO，COCH 2 OH，COCH 2 CH 3的水解和转糖基化能力），COCF 3）作为底物进行了测试。的四种新型制备p硝基苯基二糖从由酶催化的这些非天然底物的米曲霉，草酸青霉和踝节菌属菌代表了相当大的扩展糖苷酶的合成潜力。