tert-Butyl-β-D-glucopyranosid | 29074-04-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-Butyl-β-D-glucopyranosid
• 英文别名: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[(2-methylpropan-2-yl)oxy]oxane-3,4,5-triol
• CAS: 29074-04-2
• 化学式: C₁₀H₂₀O₆
• 分子量: 236.265
• InChiKey: FYTBMEIHHNSHKR-ZEBDFXRSSA-N

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：

  tert-Butyl-β-D-glucopyranosid 在 Manihot esculenta Crantz linamarase 、 sodium acetate 作用下， 以 水 为溶剂， 反应 0.08h， 生成 葡萄糖
  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
• 作为产物：
  描述：

  2-pyridyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 在 sodium methylate 、 mercury(II) nitrate 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 tert-Butyl-β-D-glucopyranosid
  参考文献：
  名称：

  Chemistry of the glycosidic linkage. Exceptionally fast and efficient formation of glycosides by remote activation

  摘要：

  DOI：

  10.1016/s0008-6215(00)84882-x

文献信息

• The tertiary-butyl group: Selective protection of the anomeric centre and evaluation of its orthogonal cleavage
  作者：Afraz Subratti、Nigel Kevin Jalsa

  DOI：10.1016/j.tetlet.2018.04.048

  日期：2018.5

  The tertiary-butyl group has not been examined extensively as a protecting group. In this work, we describe the synthesis of tert-butyl glycosides via the Fischer glycosylation protocol. Furthermore, its utility as a temporary anomeric protecting group was evaluated. A range of differentially protected monosaccharides was used to investigate the stability of the tert-butyl group upon the introduction

  在第三丁基组尚未被广泛讨论的一个保护基。在这项工作中，我们描述了通过Fischer糖基化方案合成叔丁基糖苷。此外，评估了其作为临时端基保护基的用途。一系列差异保护的单糖用于研究引入其他保护基团后叔丁基的稳定性。在后者存在下其裂解的相容性。
• Sirtuin modulating compounds
  申请人：Nunes J. Joseph

  公开号：US20070043050A1

  公开（公告）日：2007-02-22

  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.

  本文提供了一种新型的调节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，包括与衰老或应激相关的疾病或疾病，糖尿病，肥胖症，神经退行性疾病，心血管疾病，血液凝固障碍，炎症，癌症和/或潮红，以及需要增加线粒体活性的疾病或疾病。此外，还提供了包含Sirtuin调节化合物与另一种治疗药物的组合物。
• SIRTUIN MODULATING COMPOUNDS
  申请人：Nunes Joseph J.

  公开号：US20110130387A1

  公开（公告）日：2011-06-02

  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.

  本文提供了新型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、血栓形成障碍、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剂组合的组合物。
• Stereoselective protecting-group-free synthesis of alkyl glycosides using dibenzyloxy triazine type glycosyl donors
  作者：Gefei Li、Masato Noguchi、Masaki Ishihara、Yuka Takagi、Marina Nagaki、Sachie Saito、Masashi Saito、Xin-shan Ye、Shin-ichiro Shoda

  DOI：10.1016/j.carres.2023.108940

  日期：2023.12

  key step for the synthesis of sugar-containing molecules such as glycolipids. However, traditional carbohydrate chemistry is characterized by extensive use of protective groups, resulting in laborious manipulations and poor atom economy. Here, we present a protecting-group-free glycosylation strategy employing dibenzyloxy-1,3,5-triazin-2-yl glycosides (DBT-glycosides) as glycosyl donors. The DBT-glycosyl

  化学O-糖基化是合成糖脂等含糖分子的关键步骤。然而，传统的碳水化合物化学的特点是广泛使用保护基团，导致操作繁琐且原子经济性差。在这里，我们提出了一种使用二苄氧基-1,3,5-三嗪-2-基糖苷（DBT-糖苷）作为糖基供体的无保护基糖基化策略。 DBT-糖基供体可以通过水介质中未受保护的糖的碱性亲核取代直接制备。在温和的氢解条件下，使用 DBT-糖基供体对醇进行O-糖基化，以良好的产率立体选择性地提供相应的烷基糖苷。
• Compounds, compositions, and methods for treatment of diseases involving acidic or hypoxic diseased tissues
  申请人：Cybrexa 1, Inc.

  公开号：US10933069B2

  公开（公告）日：2021-03-02

  Compounds for treatment of diseases having acidic or hypoxic diseased tissues and pharmaceutical compositions comprising the compounds, as well as methods for making and using the compounds and compositions.

  用于治疗具有酸性或缺氧病变组织的疾病的化合物和包含这些化合物的药物组合物，以及制造和使用这些化合物和组合物的方法。