2,3,4-tri-O-acetyl-6-azido-6-deoxy-α-D-glucopyranose | 67647-17-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4-tri-O-acetyl-6-azido-6-deoxy-α-D-glucopyranose
• 英文别名: 2,3,4-tri-O-acetyl-6-azido-6-deoxy-D-glucopyranose；2,3,4-tri-O-acetyl-6-azido-6-deoxy-alpha-D-glucopyranose；[(2R,3R,4S,5R,6S)-4,5-diacetyloxy-2-(azidomethyl)-6-hydroxyoxan-3-yl] acetate
• CAS: 67647-17-0
• 化学式: C₁₂H₁₇N₃O₈
• 分子量: 331.282
• InChiKey: MUTUZTFDNMUQCN-ZIQFBCGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  123
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-acetyl-6-azido-6-deoxy-α-D-glucopyranose 在 palladium on activated charcoal 三氟甲磺酸三甲基硅酯 、 氢气 、 potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 29.0h， 生成 cis,cis-3,5-diaminocyclohexyl β-D-6-amino-6-deoxyglucopyranoside tri(acetic acid) salt
  参考文献：
  名称：

  Application of the Synthetic Aminosugars for Glycodiversification:  Synthesis and Antimicrobial Studies of Pyranmycin

  摘要：

  A divergent approach was employed for the synthesis of aminosugars, from which a novel library of aminoglycoside antibiotics (pyranmycins) was synthesized. Pyranmycins have comparable antibacterial activity as neomycin, a clinically used aminoglycoside antibiotic, against Escherichia coli, Staphylococcus aureus, Bacillus subtilis, and Mycobacterium smegmatis. In addition, pyranmycins, like streptomycin, are bacteriocidal while isoniazid (INH) is bacteriostatic. Therefore, pyranmycins may provide new therapeutic options in the treatment against tuberculosis. Several members of pyranmycins also manifest modest anti-Tat and anti-Rev activities, which may aid in the development of new anti-HIV agents. Although the antibacterial activity of pyranmycins against aminoglycoside resistant bacteria is less than expected, the synthetic methodologies of utilizing a library of aminosugars can be a model for future studies of glycodiversification or glycorandomization.

  DOI：

  10.1021/jo035290r
• 作为产物：
  描述：

  methyl 2,3-O-dibenzyl-4,6-O-benzylidene-α-D-glucopyranoside 在 吡啶 、 sodium azide 、 硫酸 、 乙酸肼 、 对甲苯磺酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 2,3,4-tri-O-acetyl-6-azido-6-deoxy-α-D-glucopyranose
  参考文献：
  名称：

  Application of the Synthetic Aminosugars for Glycodiversification:  Synthesis and Antimicrobial Studies of Pyranmycin

  摘要：

  A divergent approach was employed for the synthesis of aminosugars, from which a novel library of aminoglycoside antibiotics (pyranmycins) was synthesized. Pyranmycins have comparable antibacterial activity as neomycin, a clinically used aminoglycoside antibiotic, against Escherichia coli, Staphylococcus aureus, Bacillus subtilis, and Mycobacterium smegmatis. In addition, pyranmycins, like streptomycin, are bacteriocidal while isoniazid (INH) is bacteriostatic. Therefore, pyranmycins may provide new therapeutic options in the treatment against tuberculosis. Several members of pyranmycins also manifest modest anti-Tat and anti-Rev activities, which may aid in the development of new anti-HIV agents. Although the antibacterial activity of pyranmycins against aminoglycoside resistant bacteria is less than expected, the synthetic methodologies of utilizing a library of aminosugars can be a model for future studies of glycodiversification or glycorandomization.

  DOI：

  10.1021/jo035290r

文献信息

• Synthetic Glycosphingolipids for Live-Cell Labeling
  作者：Martin Dauner、Ellen Batroff、Verena Bachmann、Christof R. Hauck、Valentin Wittmann

  DOI：10.1021/acs.bioconjchem.6b00177

  日期：2016.7.20

  insight into their localization. However, the attachment of a fluorophore to the glycan part or - more commonly - to the lipid part of glycosphingolipids is known to alter the biophysical properties and can perturb the biological function of the probe. Presented here is the synthesis of novel glycosphingolipid probes with mono and disaccharide head groups and ceramide moieties containing fatty acids of varying

  糖鞘脂是涉及许多生物学过程的细胞膜的重要组成部分。荧光标记的糖鞘脂经常用于深入了解其定位。然而，已知荧光团与糖鞘脂的聚糖部分或更通常地与脂质部分的附着会改变生物物理特性，并且会干扰探针的生物学功能。本文介绍的是具有单糖和二糖首基以及神经酰胺部分的新型糖鞘脂探针的合成，所述神经酰胺部分含有链长不同的脂肪酸（C4至C20）。这些糖鞘脂具有作为化学报告基的叠氮基或炔基，可以通过生物正交连接反应将荧光团连接至其上。可以以灵活的方式选择荧光标签和与其连接的任何接头。我们通过共聚焦显微镜技术选择性观察活细胞的质膜，证明了探针的适用性。具有较短脂肪酸的衍生物可直接应用于HEK 293T细胞，而具有较长脂肪酸的疏水性鞘糖脂可使用融合脂质体递送至细胞。
• Synthesis of Bifunctional Azobenzene Glycoconjugates for Cysteine-Based Photosensitive Cross-Linking with Bioactive Peptides
  作者：Anne Müller、Hauke Kobarg、Vijayanand Chandrasekaran、Joana Gronow、Frank D. Sönnichsen、Thisbe K. Lindhorst

  DOI：10.1002/chem.201501571

  日期：2015.9.21

  Azobenzene linker molecules can be utilized to control peptide/protein function when they are ligated to appropriately spaced amino acid side chains of the peptide. This is because the photochemical E/Z isomerization of the azobenzene NN double bond allows to switch peptide conformation between folded and unfolded. In this context, we have introduced carbohydrate‐functionalized azobenzene derivatives

  当偶氮苯连接分子与适当间隔的肽氨基酸侧链连接时，可用于控制肽/蛋白质的功能。这是因为偶氮苯NN双键的光化学E / Z异构化可以在折叠和未折叠之间切换肽构象。在这种情况下，我们引入了碳水化合物官能化的偶氮苯衍生物，以提高偶氮苯肽接头的生物相容性。氯乙酰胺官能化和O合成了烯丙基化的碳水化合物衍生物，并与偶氮苯共轭以实现新的双功能交联剂，以便分别通过亲核取代或巯基反应与半胱氨酸侧链连接。确定了新的接头糖缀合物的光致变色性质，并进行了首次连接反应。
• Composition and methods related to modification of 5-hydroxymethylcytosine (5-hmC)
  申请人：He Chuan

  公开号：US08741567B2

  公开（公告）日：2014-06-03

  The present invention relates generally to the field of molecular biology. More particularly, it concerns methods and compositions for detecting, evaluating, and/or mapping 5-hydroxymethyl-modified cytosine bases within a nucleic acid molecule.

  本发明一般涉及分子生物学领域。更具体地说，涉及检测、评估和/或映射核酸分子中的5-羟甲基修饰的胞嘧啶碱基的方法和组合物。
• Composition and Methods Related to Modification of 5-Hydroxymethylcytosine (5-hmC)
  申请人：He Chuan

  公开号：US20110301045A1

  公开（公告）日：2011-12-08

  The present invention relates generally to the field of molecular biology. More particularly, it concerns methods and compositions for detecting, evaluating, and/or mapping 5-hydroxymethyl-modified cytosine bases within a nucleic acid molecule.

  本发明通常涉及分子生物学领域。更具体地，它涉及用于检测、评估和/或映射核酸分子中的5-羟甲基修饰的胞嘧啶碱基的方法和组合物。
• COMPOSITION AND METHODS RELATED TO MODIFICATION OF 5-HYDROXYMETHYLCYTOSINE (5-hmC)
  申请人：The University of Chicago

  公开号：US20150056616A1

  公开（公告）日：2015-02-26

  The present invention relates generally to the field of molecular biology. More particularly, it concerns methods and compositions for detecting, evaluating, and/or mapping 5-hydroxymethyl-modified cytosine bases within a nucleic acid molecule.

  本发明通常涉及分子生物学领域。更具体地，涉及检测、评估和/或绘制核酸分子中5-羟甲基修饰的胞嘧啶碱基的方法和组成物。