[(2R,3R,4S,5R,6R)-2-((2R,3R,4R,5S,6R)-3-Acetylamino-5-hydroxy-6-hydroxymethyl-2-octyloxy-tetrahydro-pyran-4-yloxy)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yloxy]-acetic acid | 912364-59-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3R,4S,5R,6R)-2-((2R,3R,4R,5S,6R)-3-Acetylamino-5-hydroxy-6-hydroxymethyl-2-octyloxy-tetrahydro-pyran-4-yloxy)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yloxy]-acetic acid
• 英文别名: 2-[(2R,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6R)-5-acetamido-3-hydroxy-2-(hydroxymethyl)-6-octoxyoxan-4-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxyacetic acid
• CAS: 912364-59-1
• 化学式: C₂₄H₄₃NO₁₃
• 分子量: 553.604
• InChiKey: WJLDLIKLDBFNHL-CYABAIRNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  38
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  214
• 氢给体数：
  7
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4S,5R,6R)-2-((2R,3R,4R,5S,6R)-3-Acetylamino-5-hydroxy-6-hydroxymethyl-2-octyloxy-tetrahydro-pyran-4-yloxy)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yloxy]-acetic acid 在 sodium hydroxide 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 {2-[(2R,3R,4S,5R,6R)-2-((2R,3R,4R,5S,6R)-3-Acetylamino-5-hydroxy-6-hydroxymethyl-2-octyloxy-tetrahydro-pyran-4-yloxy)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yloxy]-acetylamino}-acetic acid
  参考文献：
  名称：

  Screening for Galectin-3 Inhibitors from Synthetic Lacto-N-biose Libraries Using Microscale Affinity Chromatography Coupled to Mass Spectrometry

  摘要：

  The synthesis and screening of two beta-D-Galp-(1-3)-beta-D-GlcpN ( lacto-N-biose) disaccharide libraries are reported. Solution-phase synthetic modifications at the HO-2' and NH positions were performed in an effort to enhance the affinity toward galectin-3, a galactose-binding protein involved in tumor metastasis, apoptosis, and inflammation. The libraries were screened for galectin-3 binding by microscale frontal affinity chromatography coupled to mass spectrometry ( FAC/MS) allowing for rapid ranking of the different inhibitors and the determination of the galectin-3 binding K-d's. Compounds bearing a hydrophobic substituent on the NH group showed the highest affinity for the lectin. The N-naphthoyl derivative ( K-d = 10.6 mu M) was the best inhibitor with a 7 times increased affinity as compared to the N-acetyl parent compound ( K-d = 73.3 mu M).

  DOI：

  10.1021/jo060485v
• 作为产物：
  描述：

  1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose 在 吡啶 、 sodium hydroxide 、 N-碘代丁二酰亚胺 、 camphor-10-sulfonic acid 、 氢溴酸 、 sodium methylate 、 silver trifluoromethanesulfonate 、 氰化汞 、 sodium hydride 、 溶剂黄146 、 锌 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 22.5h， 生成 [(2R,3R,4S,5R,6R)-2-((2R,3R,4R,5S,6R)-3-Acetylamino-5-hydroxy-6-hydroxymethyl-2-octyloxy-tetrahydro-pyran-4-yloxy)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yloxy]-acetic acid
  参考文献：
  名称：

  Screening for Galectin-3 Inhibitors from Synthetic Lacto-N-biose Libraries Using Microscale Affinity Chromatography Coupled to Mass Spectrometry

  摘要：

  The synthesis and screening of two beta-D-Galp-(1-3)-beta-D-GlcpN ( lacto-N-biose) disaccharide libraries are reported. Solution-phase synthetic modifications at the HO-2' and NH positions were performed in an effort to enhance the affinity toward galectin-3, a galactose-binding protein involved in tumor metastasis, apoptosis, and inflammation. The libraries were screened for galectin-3 binding by microscale frontal affinity chromatography coupled to mass spectrometry ( FAC/MS) allowing for rapid ranking of the different inhibitors and the determination of the galectin-3 binding K-d's. Compounds bearing a hydrophobic substituent on the NH group showed the highest affinity for the lectin. The N-naphthoyl derivative ( K-d = 10.6 mu M) was the best inhibitor with a 7 times increased affinity as compared to the N-acetyl parent compound ( K-d = 73.3 mu M).

  DOI：

  10.1021/jo060485v

文献信息

• Screening for Galectin-3 Inhibitors from Synthetic Lacto-<i>N</i>-biose Libraries Using Microscale Affinity Chromatography Coupled to Mass Spectrometry
  作者：Sébastien Fort、Hyo-Sun Kim、Ole Hindsgaul

  DOI：10.1021/jo060485v

  日期：2006.9.1

  The synthesis and screening of two beta-D-Galp-(1-3)-beta-D-GlcpN ( lacto-N-biose) disaccharide libraries are reported. Solution-phase synthetic modifications at the HO-2' and NH positions were performed in an effort to enhance the affinity toward galectin-3, a galactose-binding protein involved in tumor metastasis, apoptosis, and inflammation. The libraries were screened for galectin-3 binding by microscale frontal affinity chromatography coupled to mass spectrometry ( FAC/MS) allowing for rapid ranking of the different inhibitors and the determination of the galectin-3 binding K-d's. Compounds bearing a hydrophobic substituent on the NH group showed the highest affinity for the lectin. The N-naphthoyl derivative ( K-d = 10.6 mu M) was the best inhibitor with a 7 times increased affinity as compared to the N-acetyl parent compound ( K-d = 73.3 mu M).