2-methyl-2-propyl glucoside | 100016-88-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-methyl-2-propyl glucoside
• 英文别名: tert-butyl glucoside；T-Butyl D-glucoside；(2R,3S,4S,5R)-2-(hydroxymethyl)-6-[(2-methylpropan-2-yl)oxy]oxane-3,4,5-triol
• CAS: 100016-88-4
• 化学式: C₁₀H₂₀O₆
• 分子量: 236.265
• InChiKey: FYTBMEIHHNSHKR-LOFWALOHSA-N

物化性质

• 沸点：
  397.4±42.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-methyl-2-propyl glucoside 、 乙酸酐 在 吡啶 作用下， 生成 tert-butyl-(tetra-O-acetyl-β-D-glucopyranoside) 、 O-tert-butyl-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside
  参考文献：
  名称：

  Direct Glycosylation of Bioactive Small Molecules with Glycosyl Iodide and Strained Olefin as Acid Scavenger

  摘要：

  A new strategy for diversity-oriented direct glycosylation of bioactive small molecules was developed. This reaction features (-)-beta-pinene as acid scavenger and work with glycosyl iodides under mild conditions. With the aid of RP-HPLC and chiral SFC separation techniques, the new direct glycosylation proved effective at gram scale on bioactive small molecules including AZD6244, podophyllotoxin, paclitaxel, and docetaxel. Interesting glycoside derivatives were efficiently created with good yields and 1,2-cis selectivity.

  DOI：

  10.1021/jo402551x
• 作为产物：
  描述：

  叔丁醇 、 4-硝基苯-Β-D-吡喃葡萄糖苷 在 Manihot esculenta Crantz linamarase 、 sodium acetate 作用下， 以 水 为溶剂， 反应 0.08h， 以35%的产率得到2-methyl-2-propyl glucoside
  参考文献：
  名称：

  Substrate specificity in hydrolysis and transglucosylation by family 1 β-glucosidases from cassava and Thai rosewood

  摘要：

  Thai rosewood (Dalbergia cochinchinensis Pierre) dalcochinase and cassava (Manihot esculenta Crantz) linamarase are glycoside hydrolase family 1 beta-glucosidases with 47% amino acid sequence identity. Each enzyme can hydrolyze its natural substrate, dalcochinin-8'-O-beta-D-glucoside and linamarin, respectively, but not the natural substrate of the other enzyme. Linamarase can transfer glucose to primary, secondary and tertiary alcohols with high efficiency, while dalcochinase can transglucosylate primary and secondary alcohols at moderate levels. In this study, eight amino acid residues in the aglycone binding pocket of dalcochinase were individually replaced with the corresponding residues of linamarase, in order to identify residues that may account for their catalytic differences. The residues 1185 and V255 of dalcochinase appeared important for its substrate specificity, with their respective mutations resulting in 24- and 12-fold reductions in K-cat/K-m for the hydrolysis of dalcochinin-8'-O-beta-D-glucoside. Transglucosylation activity was improved when 1185, N189 and V255 of dalcochinase were replaced with A201, F205 and F271 of linamarase, respectively, suggesting these residues support transglucosylation in linamarase. Among these three mutants, only the N189F mutant showed significant increases in the rate constants for the reactivation of trapped glucosyl-enzyme intermediates by all alcohols. Together, our results suggest that both hydrophobicity and geometry are important determinants for substrate specificity in hydrolysis and transglucosylation by these family 1 beta-glucosidases. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2010.09.003

文献信息

• Acridine and Quinoline Derivatives as Sirtuin Modulators
  申请人：Milburn Michael

  公开号：US20090069301A1

  公开（公告）日：2009-03-12

  Provided herein are novel sirtuin-modulating compounds and methods of use thereof. The sirtuin-modulating compounds may be used for increasing the lifespan of a cell, and treating and/or preventing a wide variety of diseases and disorders including, for example, diseases or disorders related to aging or stress, diabetes, obesity, neurodegenerative diseases, chemotherapeutic induced neuropathy, neuropathy associated with an ischemic event, polyglutamine diseases, ocular diseases and/or disorders, cardiovascular disease, blood clotting disorders, inflammation, cancer, and/or flushing. Also provided are compositions comprising a sirtuin-modulating compound in combination with another therapeutic agent.

  本文提供了新颖的sirtuin调节化合物及其使用方法。这些sirtuin调节化合物可用于增加细胞寿命，并治疗和/或预防各种疾病和疾病，包括与衰老或压力有关的疾病或疾病，糖尿病，肥胖症，神经退行性疾病，化疗引起的神经病理性疼痛，缺血事件相关的神经病理性疼痛，多谷氨酸疾病，眼部疾病和/或疾病，心血管疾病，血栓形成障碍，炎症，癌症和/或潮红。还提供了包含sirtuin调节化合物与另一种治疗剂组合的组合物。
• Sirtuin modulating compounds
  申请人：Nunes J. Joseph

  公开号：US20070037809A1

  公开（公告）日：2007-02-15

  Provided herein are novel sirtuin-modulating compounds and methods of use thereof. The sirtuin-modulating compounds may be used for increasing the lifespan of a cell, and treating and/or preventing a wide variety of diseases and disorders including, for example, diseases or disorders related to aging or stress, diabetes, obesity, neurodegenerative diseases, cardiovascular disease, blood clotting disorders, inflammation, cancer, and/or flushing as well as diseases or disorders that would benfit from increased mitochondrial activity. Also provided are compositions comprising a sirtuin-modulating compound in combination with another therapeutic agent.

  本文提供了新型的sirtuin调节化合物及其使用方法。这些sirtuin调节化合物可用于增加细胞寿命，并治疗和/或预防各种疾病和疾病，包括与衰老或应激有关的疾病或疾病，糖尿病，肥胖症，神经退行性疾病，心血管疾病，血液凝块性疾病，炎症，癌症和/或红斑病，以及需要增加线粒体活性的疾病或疾病。还提供了包含sirtuin调节化合物和另一种治疗剂的组合物。
• SIRTUIN MODULATING COMPOUNDS
  申请人：Nunes Joseph J.

  公开号：US20120197013A1

  公开（公告）日：2012-08-02

  Provided herein are novel sirtuin-modulating compounds and methods of use thereof. The sirtuin-modulating compounds may be used for increasing the lifespan of a cell, and treating and/or preventing a wide variety of diseases and disorders including, for example, diseases or disorders related to aging or stress, diabetes, obesity, neurodegenerative diseases, cardiovascular disease, blood clotting disorders, inflammation, cancer, and/or flushing as well as diseases or disorders that would benefit from increased mitochondrial activity. Also provided are compositions comprising a sirtuin-modulating compound in combination with another therapeutic agent.

  本文提供了一种新颖的调节沉默信息调节因子（sirtuin）的化合物及其使用方法。这些调节sirtuin的化合物可用于延长细胞寿命，并用于治疗和/或预防多种疾病和障碍，包括与衰老或应激有关的疾病或障碍、糖尿病、肥胖症、神经退行性疾病、心血管疾病、血液凝结障碍、炎症、癌症和/或潮红，以及需要增加线粒体活性的疾病或障碍。还提供了包含sirtuin调节化合物与另一种治疗药物组合的组合物。
• N-Phenyl Benzamide Derivatives as Sirtuin Modulators
  申请人：Milburn Michael

  公开号：US20090163476A1

  公开（公告）日：2009-06-25

  Provided herein are novel sirtuin-modulating compounds and methods of use thereof. The sirtuin-modulating compounds may be used for increasing the lifespan of a cell, and treating and/or preventing a wide variety of diseases and disorders including, for example, diseases or disorders related to aging or stress, diabetes, obesity, neurodegenerative diseases, cardiovascular disease, blood clotting disorders, inflammation, cancer, and/or flushing as well as diseases or disorders that would benefit from increased mitochondrial activity. Also provided are compositions comprising a sirtuin-modulating compound in combination with another therapeutic agent.

  本文提供了新型的调节sirtuin的化合物及其使用方法。这些sirtuin调节化合物可用于延长细胞寿命，以及治疗和/或预防各种疾病和障碍，包括与衰老或压力有关的疾病或障碍、糖尿病、肥胖症、神经退行性疾病、心血管疾病、血液凝结障碍、炎症、癌症和/或潮红，以及可以受益于增加线粒体活性的疾病或障碍。还提供了包含sirtuin调节化合物与另一种治疗剂的组合物。
• ANTI-WRINKLE AGENT AND ADAM INHIBITOR
  申请人：Shiseido Company, Ltd.

  公开号：EP2127636A1

  公开（公告）日：2009-12-02

  Disclosed is an anti-wrinkle agent for ameliorating a wrinkle (particularly a fine wrinkle) developed when the barrier function is decreased by dryness and the like. Also disclosed is an ADAM inhibitor. The anti-wrinkle agent or the ADAM inhibitor comprises an alkyl glucoside represented by the general formula: (1) [wherein R represents a linear or branched alkyl group having 1 to 18 carbon atoms] or a salt thereof.

  本发明公开了一种抗皱剂，用于改善因干燥等原因导致屏障功能降低时产生的皱纹（尤其是细小皱纹）。还公开了一种 ADAM 抑制剂。抗皱剂或 ADAM 抑制剂包括由通式表示的烷基葡萄糖苷：(1) [其中 R 代表具有 1 至 18 个碳原子的直链或支链烷基]或其盐。

表征谱图