2-hydroxyethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside | 1219118-40-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-hydroxyethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside
• 英文别名: 2-hydroxyethyl 3,4,6-tri-O-acetyl-2-acetylamino-2-deoxy-β-D-glucopyranose；2-hydroxyethyl-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside
• CAS: 1219118-40-7
• 化学式: C₁₆H₂₅NO₁₀
• 分子量: 391.375
• InChiKey: WAZAUXIDPAKAKN-OXGONZEZSA-N

物化性质

• 沸点：
  575.3±50.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.35
• 重原子数：
  27.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  146.69
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  2-hydroxyethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 在 Jones reagent 作用下， 以 丙酮 为溶剂， 反应 13.0h， 以73%的产率得到2-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-diacetoxy-6-(acetoxymethyl)tetrahydropyran-2-yl]oxyacetatic acid
  参考文献：
  名称：

  [EN] SILICON PARTICLES TARGETING TUMOR CELLS
  [FR] PARTICULES DE SILICIUM CIBLANT LES CELLULES TUMORALES

  摘要：

  一种硅颗粒，包括硅体、包围硅体的功能化二氧化硅表面，以及特异性靶向肿瘤细胞的靶向基团，以及可选的酶代谢化合物，在颗粒内部化后通过诱导细胞死亡，在癌症治疗中具有用处。

  公开号：

  WO2015177340A1
• 作为产物：
  描述：

  1-bromo-2-deoxy-2-N-phthalimido-3,4,6-tri-O-acetyl-β-D-glucopyranose 在 吡啶 、 4-二甲氨基吡啶 、 氢气 、 palladium(II) hydroxide 、 silver carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 104.0h， 生成 2-hydroxyethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Effects of Sugar Functional Groups, Hydrophobicity, and Fluorination on Carbohydrate–DNA Stacking Interactions in Water

  摘要：

  Carbohydrate-aromatic interactions are highly relevant for many biological processes. Nevertheless, experimental data in aqueous solution relating structure and energetics for sugar-arene stacking interactions are very scarce. Here, we evaluate how structural variations in a monosaccharide including carboxyl, N-acetyl, fluorine, and methyl groups affect stacking interactions with aromatic DNA bases. We find small differences on stacking interaction among the natural carbohydrates examined. The presence of fluorine atoms within the pyranose ring slightly increases the interaction with the C-G DNA base pair. Carbohydrate hydrophobicity is the most determinant factor. However, gradual increase in hydrophobicity of the carbohydrate does not translate directly into a steady growth in stacking interaction. The energetics correlates better with the amount of apolar surface buried upon sugar stacking on top of the aromatic DNA base pair.

  DOI：

  10.1021/jo402700y

文献信息

• Chemo-enzymatic synthesis of glycosylated insulin using a GlcNAc tag
  作者：Yusuke Tomabechi、Rena Suzuki、Katsuji Haneda、Toshiyuki Inazu

  DOI：10.1016/j.bmc.2009.12.031

  日期：2010.2

  Artificial insulin with an N-linked oligosaccharide was synthesized by a chemo-enzymatic method using endo-beta-N-acetylglucosaminidase from Mucor hiemalis (Endo-M). GlcNAc-modified insulin was prepared by the reaction of the carboxymethyl glycoside of GlcNAc and 3 amino groups of bovine insulin using a dimethylphosphinothioic mixed anhydride (Mpt-MA) method. A transglycosylation reaction of the GlcNAc-modified insulin using Endo-M gave mono-transglycosylated insulin predominantly. We determined the transglycosylation site of the mono-transglycosylated insulin. (C) 2009 Elsevier Ltd. All rights reserved.