O-(2-Acetamido-2-desoxy-β-D-glucopyranosyl)-(1->3)-O-(β-D-galactopyranosyl)-(1->4)-β-D-glucopyranose | 24741-60-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(2-Acetamido-2-desoxy-β-D-glucopyranosyl)-(1->3)-O-(β-D-galactopyranosyl)-(1->4)-β-D-glucopyranose
• 英文别名: GlcNAcbeta1-3Galbeta1-4Glcbeta；N-[(2S,3R,4R,5S,6R)-2-[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-[(2R,3S,4R,5R,6R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxan-4-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 24741-60-4
• 化学式: C₂₀H₃₅NO₁₆
• 分子量: 545.495
• InChiKey: CRTJRHPGCOAOQC-QLFGYAPHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.3
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  278
• 氢给体数：
  11
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  O-(2-Acetamido-2-desoxy-β-D-glucopyranosyl)-(1->3)-O-(β-D-galactopyranosyl)-(1->4)-β-D-glucopyranose 在 碳酸氢铵 作用下， 以 二甲基亚砜 为溶剂， 反应 72.0h， 以66%的产率得到N-((2S,3R,4R,5S,6R)-2-(((2S,3R,4S,5S,6R)-2-(((2R,3S,4R,5R,6R)-6-amino-4,5-dihydroxy-2-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)oxy)-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl)oxy)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide
  参考文献：
  名称：

  Bioorthogonal human milk oligosaccharide probes for antimicrobial target identification within Streptococcus agalactiae

  摘要：

  Human milk oligosaccharides (HMOs) are a structurally diverse class of carbohydrates that possess strong antibacterial activity against Streptococcus agalactiae (Group B Strep, GBS). This work highlights the design, synthesis, and retained biological activity of several HMO bioorthogonal probes within GBS, a first in class advance. The use of such probes will assist in identifying HMO-protein interactions within GBS and may be broadly applicable in researching HMO cellular targets within a variety of biological systems. Finally, this strategy is highly amenable to other oligosaccharide scaffolds, requiring minimal synthetic transformations and chemical perturbation.

  DOI：

  10.1016/j.carres.2019.107895
• 作为产物：
  描述：

  Benzyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-(1->3)-O-(4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranosid 在 palladium on activated charcoal 氢气 、 sodium methylate 作用下， 以 1,4-二氧六环 、 甲醇 、 氯仿 、 水 为溶剂， 反应 124.0h， 生成 O-(2-Acetamido-2-desoxy-β-D-glucopyranosyl)-(1->3)-O-(β-D-galactopyranosyl)-(1->4)-β-D-glucopyranose
  参考文献：
  名称：

  Paulsen, Hans; Hadamczyk, Doris; Kutschker, Wolfram, Liebigs Annalen der Chemie, 1985, # 1, p. 129 - 141

  摘要：

  DOI：

文献信息

• GLYCOSIDE-CONTAINING LIPOSOME
  申请人：Otsuka Pharmaceutical Company, Limited

  公开号：EP1647277A1

  公开（公告）日：2006-04-19

  A drug product which can maximize the effect of a cholestanol glycoside useful as an anticancer agent. The present invention provides a liposomal composition containing a glycoside exhibiting antitumor activity, a phospholipid, and a positive-charge-providing substance; the glycoside being composed of GlcNAc-Gal-, GlcNAc-Gal-Glc-, Fuc-Gal-, Gal-Glc-, or Gal- as a sugar moiety, and a hydrophobic compound capable of forming a liposome.

  一种能够最大限度地发挥胆甾醇苷作为抗癌剂的作用的药物产品。本发明提供了一种脂质体组合物，其中含有一种具有抗肿瘤活性的糖苷、一种磷脂和一种提供正电荷的物质；该糖苷由作为糖基的GlcNAc-Gal-、GlcNAc-Gal-Glc-、Fuc-Gal-、Gal-Glc-或Gal-和一种能够形成脂质体的疏水性化合物组成。
• Glycoside-containing liposome
  申请人：Yazawa Shin

  公开号：US20060193903A1

  公开（公告）日：2006-08-31

  A drug product which can maximize the effect of a cholestanol glycoside useful as an anticancer agent. The present invention provides a liposomal composition containing a glycoside exhibiting antitumor activity, a phospholipid, and a positive-charge-providing substance; the glycoside being composed of GlcNAc-Gal-, GlcNAc-Gal-Glc-, Fuc-Gal-, Gal-Glc-, or Gal- as a sugar moiety, and a hydrophobic compound capable of forming a liposome.

  一种能够最大限度地发挥胆甾醇苷作为抗癌剂的作用的药物产品。本发明提供了一种脂质体组合物，其中含有一种具有抗肿瘤活性的糖苷、一种磷脂和一种提供正电荷的物质；该糖苷由作为糖基的GlcNAc-Gal-、GlcNAc-Gal-Glc-、Fuc-Gal-、Gal-Glc-或Gal-和一种能够形成脂质体的疏水性化合物组成。
• US7465753B2
  申请人：——

  公开号：US7465753B2

  公开（公告）日：2008-12-16