2,3,4-tri-O-benzyl-α-D-fucopyranosyl-(1->3)-2,4,6-tri-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl azide | 478687-13-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4-tri-O-benzyl-α-D-fucopyranosyl-(1->3)-2,4,6-tri-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl azide
• CAS: 478687-13-7
• 化学式: C₅₁H₆₁N₃O₂₀
• 分子量: 1036.05
• InChiKey: NHEFHXYUVOJAOC-QOQQXKSKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.87
• 重原子数：
  74.0
• 可旋转键数：
  22.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  280.4
• 氢给体数：
  0.0
• 氢受体数：
  21.0

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-benzyl-α-D-fucopyranosyl-(1->3)-2,4,6-tri-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl azide 在 platinum(IV) oxide 、 palladium dihydroxide 氢气 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 24.0h， 生成 α-D-fucopyranosyl-(1->3)-β-D-galactopyranosyl-(1->4)-N-acetyl-β-D-glucopyranosylamine
  参考文献：
  名称：

  The synthesis of deoxy-α-Gal epitope derivatives for the evaluation of an anti-α-Gal antibody binding

  摘要：

  alpha-Gal epitopes (also termed as alpha-Gal) are carbohydrate structures bearing the alpha-D-Gal-(1 --> 3)-beta-D-Gal terminus 1 and are known to be the antigen responsible for antibody-mediated hyperacute rejection in xenotransplantation. Terminal 2-, 3-, 4-, and 6-deoxy-Gal derivatives of alpha-Gal were synthesized. Inhibition ELISA using mouse laminin was established to determine the binding affinity of the synthesized alpha-Gal derivatives. 4-Deoxy-alpha-Gal derivative 7 showed a significant reduction in antibody recognition. The IC50 value was 15-fold poorer than the standard alpha-Gal epitopes alpha-D-Gal-(1 --> 3)-beta-D-Gal-(1 --> 4)-beta-D-Glc-NHAc (39) and alpha-D-Gal-(1 --> 3)-beta-D-Gal-(1 -- 4)-beta-D-Glc-OBn (40). A similar observation was seen with 2-deoxy-alpha-Gal derivative 5, whose IC50 value was nearly tenfold higher than the standards. Interestingly, substitution at the terminal 3-position resulted in only a fourfold decrease in antibody recognition, suggesting a possible point of future derivation. Finally, 6-deoxy-alpha-Gal derivative 8 exhibited similar antibody recognition to both alpha-Gal epitope 39 and alpha-Gal epitope 40. This strongly suggests that derivatization at the 6-position can be accomplished without loss of antibody recognition. These findings can be utilized for the future design of other alpha-Gal derivatives. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00159-3
• 作为产物：
  描述：

  phenyl 2,3,4-tri-O-acetyl-1-thio-β-D-fucopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 2,3,4-tri-O-benzyl-α-D-fucopyranosyl-(1->3)-2,4,6-tri-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl azide
  参考文献：
  名称：

  The synthesis of deoxy-α-Gal epitope derivatives for the evaluation of an anti-α-Gal antibody binding

  摘要：

  alpha-Gal epitopes (also termed as alpha-Gal) are carbohydrate structures bearing the alpha-D-Gal-(1 --> 3)-beta-D-Gal terminus 1 and are known to be the antigen responsible for antibody-mediated hyperacute rejection in xenotransplantation. Terminal 2-, 3-, 4-, and 6-deoxy-Gal derivatives of alpha-Gal were synthesized. Inhibition ELISA using mouse laminin was established to determine the binding affinity of the synthesized alpha-Gal derivatives. 4-Deoxy-alpha-Gal derivative 7 showed a significant reduction in antibody recognition. The IC50 value was 15-fold poorer than the standard alpha-Gal epitopes alpha-D-Gal-(1 --> 3)-beta-D-Gal-(1 --> 4)-beta-D-Glc-NHAc (39) and alpha-D-Gal-(1 --> 3)-beta-D-Gal-(1 -- 4)-beta-D-Glc-OBn (40). A similar observation was seen with 2-deoxy-alpha-Gal derivative 5, whose IC50 value was nearly tenfold higher than the standards. Interestingly, substitution at the terminal 3-position resulted in only a fourfold decrease in antibody recognition, suggesting a possible point of future derivation. Finally, 6-deoxy-alpha-Gal derivative 8 exhibited similar antibody recognition to both alpha-Gal epitope 39 and alpha-Gal epitope 40. This strongly suggests that derivatization at the 6-position can be accomplished without loss of antibody recognition. These findings can be utilized for the future design of other alpha-Gal derivatives. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00159-3