1,3,4,6-四-O-乙酰基-2-脱氧-2-[(2-叠氮乙酰基)氨基]-β-D-吡喃葡萄糖 | 857677-98-6

• 物质功能分类: 医药中间体 - 吡喃类化合物
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1,3,4,6-四-O-乙酰基-2-脱氧-2-[(2-叠氮乙酰基)氨基]-β-D-吡喃葡萄糖
• 英文名称: 1,3,4,6-tetra-O-acetyl-2-N-acetyl-2-deoxy-β-D-glucopyranose
• 英文别名: 1,3,4,6-tetra-O-acetyl-2-azidoacetamido-2-deoxy-β-D-glucopyranose；peracetylated N-azidoacetylglucosamine；1,3,4,6-tetra-O-acetyl-2-N-azidoacetyl-2-deoxy-β-D-glucopyranose；N-Azidoacetyl-D-glucosamin-1β,3,4,6-tetraacetat；Tetra-O-acetyl-2-(azidoacetyl-amino)-2-desoxy-β-D-glucopyranose；tetra-O-acetyl-2-(azidoacetyl-amino)-2-deoxy-β-D-glucopyranose；1,3,4,6-tetra-O-acetyl-2-azidoacetamide-2-deoxy-β-D-glucopyranose；[(2R,3S,4R,5R,6S)-3,4,6-triacetyloxy-5-[(2-azidoacetyl)amino]oxan-2-yl]methyl acetate
• CAS: 857677-98-6
• 化学式: C₁₆H₂₂N₄O₁₀
• 分子量: 430.371
• InChiKey: HGMISDAXLUIXKM-JPIRQXTESA-N

物化性质

• 熔点：
  131 °C (decomp)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  158
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  1,3,4,6-四-O-乙酰基-2-脱氧-2-[(2-叠氮乙酰基)氨基]-β-D-吡喃葡萄糖 在 氨 作用下， 以 甲醇 为溶剂， 生成 N-Azidoacetyl-glucosamin
  参考文献：
  名称：

  Bertho,A. et al., Justus Liebigs Annalen der Chemie, 1962, vol. 651, p. 185 - 194

  摘要：

  DOI：
• 作为产物：
  描述：

  1,3,4,6-tetra-O-acetyl-2-deoxy-2-(4-methoxybenzylidene)amino-β-D-glucopyranose 在 盐酸 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 3.0h， 生成 1,3,4,6-四-O-乙酰基-2-脱氧-2-[(2-叠氮乙酰基)氨基]-β-D-吡喃葡萄糖
  参考文献：
  名称：

  Synthesis of NAG-thiazoline-derived inhibitors for β-N-acetyl-d-hexosaminidases

  摘要：

  beta-N-Acetyl-D-hexosaminidases are responsible for the metabolism of glycoconjugates in diverse physiological processes that are important targets for medicine and pesticide development. Fourteen new NAG-thiazoline derivatives were synthesized by cyclization and click reaction using D-glucosamine hydrochloride as the starting material. All the compounds created were characterized by NMR and HRMS spectra. A preliminary bioassay, using four enzymes from two beta-N-acetyl-D-hexosaminidase families, showed that most of the compounds synthesized exhibit selective inhibition of GH84 beta-N-acetyl-D-hexosaminidase. Among the compounds tested, compounds 5a (IC50 = 12.6 mu M, hOGA) and 5e (IC50 = 12.5 mu M, OfOGA) proved to be a highly selective and potent inhibitor. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2015.06.004

文献信息

• Glucosamine- and galactosamine- based monosaccharides with highly fluorinated motifs
  作者：Joanna Tomaszewska、Karolina Kowalska、Katarzyna Koroniak-Szejn

  DOI：10.1016/j.jfluchem.2016.09.002

  日期：2016.11

  Synthesis of modified monosaccharides, derivatives of glucose and galactose, having a highly fluorinated chain, as a library of synthetic building blocks for hyaluronic acid (HA) modified subunits has been developed. “Click” chemistry has been employed as a strategy for the synthesis of these molecules. 1,2,3-triazole ring derivatives were obtained with good to excellent yields.

  已经开发了具有高度氟化的链的修饰的单糖，葡萄糖和半乳糖的衍生物的合成，作为透明质酸（HA）修饰的亚基的合成构件库。“点击”化学已被用作合成这些分子的策略。获得1,2,3-三唑环衍生物，具有良好至优异的产率。
• The synthesis of new fluorinated or nonfluorinated sugar phosphonates and phosphoramidates as building blocks in the synthesis of modified hyaluronic acid subunits
  作者：Katarzyna Koroniak-Szejn、Joanna Tomaszewska、Henryk Koroniak

  DOI：10.1080/10426507.2017.1311332

  日期：2017.6.3

  ABSTRACT ABSTRACT The synthesis of several new fluorinated or nonfluorinated sugar phosphonates and phosphoramidates as building blocks for the synthesis of modified hyaluronic acid subunits is described. These compounds were prepared from d-glucose and d-glucosamine hydrochloride. The syntheses of phosphonates and phosphoramidates are based on arbuzov and staudinger reactions. The products were fully

  图形摘要 摘要 描述了几种新的氟化或非氟化糖膦酸酯和氨基磷酸酯的合成，作为合成修饰透明质酸亚基的结构单元。这些化合物由 d-葡萄糖和 d-氨基葡萄糖盐酸盐制备。膦酸酯和氨基磷酸酯的合成基于 arbuzov 和 staudinger 反应。产物通过 1H、13C、19F、31P NMR 和 ESI MS 光谱进行了全面表征。
• Synthesis of a Novel Fluorescent Ruthenium Complex with an Appended Ac4GlcNAc Moiety by Click Reaction
  作者：Qi Cheng、Yalu Cui、Nao Xiao、Jishun Lu、Chen-Jie Fang

  DOI：10.3390/molecules23071649

  日期：——

  possible. Here we report a strategy based on the 1,3-dipolar cycloaddition, called click chemistry, between unnatural N-acetylglucosamine (GlcNAc) analogues Ac₄GlcNAc (substituted with an azido group) and the corresponding fluorescent tag Ru(bpy)₂(Phen-alkyne)Cl₂ (4) to synthesize the fluorescent dye Ru(bpy)₂(Phen-Ac₄GlcNAc)Cl₂ (5) under mild and neutral reaction conditions. Moreover, 5 showed good stability

  O-连接的β-N-乙酰氨基葡萄糖（O-GlcNAc）修饰是真核细胞中大量的翻译后修饰，在许多细胞的活动中起着根本性的作用，并与II型糖尿病，阿尔茨海默氏病或一些癌症。但是，在大多数情况下，O-GlcNAc修饰的蛋白与其在细胞中的功能之间的精确连接在很大程度上尚不确定。共聚焦显微镜是用于细胞内阐明生物分子功能的强大而有效的工具。用荧光标签化学标记非紫外线或非荧光碳水化合物是使细胞内显微镜检查成为可能的重要步骤。在这里，我们报告一种基于1,3-偶极环加成的策略，称为点击化学，非天然N-乙酰氨基葡糖（GlcNAc）类似物Ac₄GlcNAc（被叠氮基取代）与相应的荧光标记Ru（bpy）2（苯炔）Cl 2（4）之间合成荧光染料Ru（bpy）2（Phen-Ac₄GlcNAc Cl 2（5）在温和和中性的反应条件下。而且，5显示出良好的稳定性，令人满意的荧光特性，并且对敏感的MCF-7细胞表现出相当低的
• O-GlcNAc Peptide Epoxyketones Are Recognized by Mammalian Proteasomes
  作者：Martin D. Witte、Bogdan I. Florea、Martijn Verdoes、Oloruntosin Adeyanju、Gijs A. Van der Marel、Herman S. Overkleeft

  DOI：10.1021/ja901231w

  日期：2009.9.2

  Cytosolic and nuclear proteins may be subject to both O-GlcNAcylation and proteasomal degradation. By means of activity-based profiling, we demonstrate that O-GlcNAc serine-containing peptide epoxyketones bind to the proteasome catalytic active sites and thus provide the first clear evidence that proteasomes recognize peptides post-translationally modified with a GlcNAc moiety.
• Bertho; Maier, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1933, vol. 222, p. 139,144
  作者：Bertho、Maier

  DOI：——

  日期：——