O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-N-oxysuccinimide | 1238214-18-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-N-oxysuccinimide
• 英文别名: 1-[(2,3,4,6-tetra-O-acetyl-α-D-galactosyl)oxy]-2,5-pyrrolidinedione
• CAS: 1238214-18-0
• 化学式: C₁₈H₂₃NO₁₂
• 分子量: 445.38
• InChiKey: FXFOHFDUFLAHFG-COWMOVNHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.85
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  161.04
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-N-oxysuccinimide 在 肼 作用下， 以 甲醇 为溶剂， 以92%的产率得到Gal-α-ONH2
  参考文献：
  名称：

  Efficient synthesis of galactosylceramide analogues for iNKT cell stimulation

  摘要：

  Glycolipids are potential antigens for iNKT cells recognition and demonstrate important roles in both innate and adaptive immunity. However, the difficulties in the preparation of pure configuration defined glycolipids limit the exploration of their different profiles in activating iNKT cells. We report here a concise and stereospecific preparation of novel galactosylceramide analogues by oxime ligation. This strategy would provide an efficient way to generate varied glycolipid analogues with either synthetic or natural carbohydrates for biological evaluations. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.05.045
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 beta-D-半乳糖五乙酸酯 在 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 以61%的产率得到O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-N-oxysuccinimide
  参考文献：
  名称：

  Efficient synthesis of galactosylceramide analogues for iNKT cell stimulation

  摘要：

  Glycolipids are potential antigens for iNKT cells recognition and demonstrate important roles in both innate and adaptive immunity. However, the difficulties in the preparation of pure configuration defined glycolipids limit the exploration of their different profiles in activating iNKT cells. We report here a concise and stereospecific preparation of novel galactosylceramide analogues by oxime ligation. This strategy would provide an efficient way to generate varied glycolipid analogues with either synthetic or natural carbohydrates for biological evaluations. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.05.045

文献信息

• Preparation and functional analysis of gossypols having two carbohydrate appendages with enaminooxy linkages
  作者：Yoshitsugu Amano、Masaki Nakamura、Shinya Shiraishi、Naoto Chigira、Nobuya Shiozawa、Masahito Hagio、Tomohiro Yano、Teruaki Hasegawa

  DOI：10.1016/j.carres.2018.02.001

  日期：2018.3

  We developed new gossypol (Gos)-based glycoconjugates through dehydration condensation of native Gos and chemically modified glycosides having aminooxy groups. The resultant glycoconjugates (glycoGos) were resistant to hydrolysis, although they were light-sensitive and slowly decomposed even under indoor lighting. The glycoGos also exhibited improved water solubility compared with native Gos, but their saturated concentrations in water were still low (6.4-17 mu M), due to their hydrophobic naphthyl rings. We also carried out WST-8 assays to assess the anticancer activity of the glycoGos on DLD-1 and HepG2 cells and found that the glycoGos having beta-lactosides and having beta-galactosides (specific ligands for asialoglycoprotein receptors) showed enhanced anticancer activity on HepG2 cells. (c) 2018 Elsevier Ltd. All rights reserved.