(2S)-5-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-2-(9-fluorenylmethyloxycarbonylamino)pentanoic acid | 856668-34-3

• 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: (2S)-5-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-2-(9-fluorenylmethyloxycarbonylamino)pentanoic acid
• 英文别名: (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-[(2R,3S,4R,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]pentanoic acid
• CAS: 856668-34-3
• 化学式: C₃₄H₃₉NO₁₃
• 分子量: 669.683
• InChiKey: HRGXOYGDTVCJCZ-YWTJPTAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  48
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  190
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  (2S)-5-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-2-(9-fluorenylmethyloxycarbonylamino)pentanoic acid 、 Fmoc-甘氨酸 、 alkaline earth salt of/the/ methylsulfuric acid 以92%的产率得到
  参考文献：
  名称：

  C-Linked Galactosyl Serine AFGP Analogues as Potent Recrystallization Inhibitors

  摘要：

  A series of C-linked antifreeze glycoprotein analogues have been prepared to evaluate antifreeze activity as a function of distance between the carbohydrate moiety and polypeptide backbone. The building blocks for these analogues were prepared using either an olefin cross-metathesis or catalytic asymmetric hydrogenation. Analysis of antifreeze protein-specific activity revealed that only analogue 2a (n = 1) was a potent recrystallization inhibitor and thus has potential medical and industrial applications.

  DOI：

  10.1021/ol050677x
• 作为产物：
  描述：

  benzyl (2S)-5-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-2-(benzyloxycarbonylamino)pent-3-enoate 在 palladium on activated charcoal 氢气 、 碳酸氢钠 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 5.0h， 生成 (2S)-5-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-2-(9-fluorenylmethyloxycarbonylamino)pentanoic acid
  参考文献：
  名称：

  C-Linked Galactosyl Serine AFGP Analogues as Potent Recrystallization Inhibitors

  摘要：

  A series of C-linked antifreeze glycoprotein analogues have been prepared to evaluate antifreeze activity as a function of distance between the carbohydrate moiety and polypeptide backbone. The building blocks for these analogues were prepared using either an olefin cross-metathesis or catalytic asymmetric hydrogenation. Analysis of antifreeze protein-specific activity revealed that only analogue 2a (n = 1) was a potent recrystallization inhibitor and thus has potential medical and industrial applications.

  DOI：

  10.1021/ol050677x