N-[O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-1-β-D-glucopyranosyl]-2-(2-methoxyethoxy)acetamide | 635302-13-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-1-β-D-glucopyranosyl]-2-(2-methoxyethoxy)acetamide
• CAS: 635302-13-5
• 化学式: C₆₃H₇₇NO₂₄
• 分子量: 1232.3
• InChiKey: ZXOAKKHYGSLYNV-FGMQBRRPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.54
• 重原子数：
  88.0
• 可旋转键数：
  31.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  288.43
• 氢给体数：
  1.0
• 氢受体数：
  24.0

反应信息

• 作为反应物：
  描述：

  N-[O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-1-β-D-glucopyranosyl]-2-(2-methoxyethoxy)acetamide 在 palladium on activated charcoal 氢气 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 7.0h， 生成 N-[O-α-D-galactopyranosyl-(1->3)-O-β-D-galactopyranosyl-(1->4)-1-β-D-glucopyranosyl]-2-(2-methoxyethoxy)acetamide
  参考文献：
  名称：

  Frontal Affinity Chromatography Coupled to Mass Spectrometry: An Effective Method for K_dDetermination and Screening of α‐Gal Derivatives Binding to Anti‐Gal Antibodies (IgG)

  摘要：

  Frontal affinity chromatography with mass spectrometric detection (FAC/MS) was developed as an effective method for rapid determination of K-d values for alpha-Gal derivatives binding to human anti-Gal IgG antibodies. Using this method, K-d values for 23 alpha-Gal compounds were determined for the first time, including an alpha-Gal terminated N-linked oligosaccharide which mimics a single N-glycoform present on the surface of animal cells. A mixture of eight alpha-Gal derivatives, a model for an alpha-Gal compound library, was successfully screened against this anti-Gal IgG using FAC/MS. The analyte breakthrough sequence, indicated by the ion chromatogram, reflected the magnitude of the K-d values, confirming its potential application in the screening of new alpha-Gal derivatives and mimetics. Ten alpha-Gal derivatives were designed and synthesized chemically or enzymatically. Among the compounds analyzed, trivalent compound 26 demonstrated the strongest binding affinity to anti-Gal IgG with a K-d value of 3.1 muM. The alpha-Gal terminated N-linked oligosaccharide 28 had a K-d value of 8.6 muM.

  DOI：

  10.1081/car-120025323
• 作为产物：
  描述：

  O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-1-β-D-glucopyranosyl azide 在 platinum(IV) oxide 2-isobutoxy-1-isobutoxycarbonyl-1,2-dihydroquinoline 、 氢气 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、310.26 kPa 条件下， 反应 1.0h， 生成 N-[O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-1-β-D-glucopyranosyl]-2-(2-methoxyethoxy)acetamide
  参考文献：
  名称：

  Frontal Affinity Chromatography Coupled to Mass Spectrometry: An Effective Method for K_dDetermination and Screening of α‐Gal Derivatives Binding to Anti‐Gal Antibodies (IgG)

  摘要：

  Frontal affinity chromatography with mass spectrometric detection (FAC/MS) was developed as an effective method for rapid determination of K-d values for alpha-Gal derivatives binding to human anti-Gal IgG antibodies. Using this method, K-d values for 23 alpha-Gal compounds were determined for the first time, including an alpha-Gal terminated N-linked oligosaccharide which mimics a single N-glycoform present on the surface of animal cells. A mixture of eight alpha-Gal derivatives, a model for an alpha-Gal compound library, was successfully screened against this anti-Gal IgG using FAC/MS. The analyte breakthrough sequence, indicated by the ion chromatogram, reflected the magnitude of the K-d values, confirming its potential application in the screening of new alpha-Gal derivatives and mimetics. Ten alpha-Gal derivatives were designed and synthesized chemically or enzymatically. Among the compounds analyzed, trivalent compound 26 demonstrated the strongest binding affinity to anti-Gal IgG with a K-d value of 3.1 muM. The alpha-Gal terminated N-linked oligosaccharide 28 had a K-d value of 8.6 muM.

  DOI：

  10.1081/car-120025323