Acetic acid (2R,3S,4S,5R,6R)-5-acetoxy-2-acetoxymethyl-6-{2-[2-(2-amino-ethoxy)-ethoxy]-ethoxy}-4-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester | 725250-84-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2R,3S,4S,5R,6R)-5-acetoxy-2-acetoxymethyl-6-{2-[2-(2-amino-ethoxy)-ethoxy]-ethoxy}-4-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester
• CAS: 725250-84-0
• 化学式: C₅₂H₆₅NO₁₆
• 分子量: 960.085
• InChiKey: YUOPHOAQKBPUEN-ZTYSIUSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.23
• 重原子数：
  69.0
• 可旋转键数：
  28.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  197.22
• 氢给体数：
  1.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  1,3,5-苯三甲酰氯 、 Acetic acid (2R,3S,4S,5R,6R)-5-acetoxy-2-acetoxymethyl-6-{2-[2-(2-amino-ethoxy)-ethoxy]-ethoxy}-4-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 13.0h， 以83%的产率得到1,3,5-tris{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->8)-3,6-dioxaoctyl]carbamido}benzene
  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：

  1-Chloro-3,6-dioxaoct-8-yl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 在 platinum(IV) oxide 吡啶 、 4-二甲氨基吡啶 、 sodium azide 、 2,6-二叔丁基-4-甲基吡啶 、 ammonium cerium(IV) nitrate 、 4 A molecular sieve 、 氢气 、 二正丁基氧化锡 、 sodium carbonate 、 三氟甲烷磺酸甲酯 作用下， 以 甲醇 、 乙醚 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 20.0~80.0 ℃ 、405.3 kPa 条件下， 反应 100.0h， 生成 Acetic acid (2R,3S,4S,5R,6R)-5-acetoxy-2-acetoxymethyl-6-{2-[2-(2-amino-ethoxy)-ethoxy]-ethoxy}-4-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester
  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