O-(5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosylonic-acid)-(2-3)-O-β-D-galactopyranosyl-(1-3)-2-acetamido-2-deoxy-α-D-glucopyranose | 142434-21-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosylonic-acid)-(2-3)-O-β-D-galactopyranosyl-(1-3)-2-acetamido-2-deoxy-α-D-glucopyranose
• 英文别名: NeuAc(a2-3)Gal(b1-3)a-GlcNAc；(2S,4S,5R,6R)-5-acetamido-2-[(2R,3R,4S,5S,6R)-2-[(2S,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• CAS: 142434-21-7
• 化学式: C₂₅H₄₂N₂O₁₉
• 分子量: 674.61
• InChiKey: KMRCGPSUZRGVOV-YNBGFLMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.7
• 重原子数：
  46
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  344
• 氢给体数：
  13
• 氢受体数：
  19

反应信息

• 作为产物：
  描述：

  lacto-N-biose 、 alkaline earth salt of/the/ methylsulfuric acid 生成 (2S,4S,5R,6R)-5-乙酰氨基-2-[(2R,3R,4S,5S,6R)-2-[(2R,3R,4R,5S,6R)-3-乙酰氨基-2,5-二羟基-6-(羟基甲基)四氢吡喃-4-基]氧基-3,5-二羟基-6-(羟基甲基)四氢吡喃-4-基]氧基-4-羟基-6-[(1R,2R)-1,2,3-三羟基丙基]四氢吡喃-2-羧酸 、 O-(5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosylonic-acid)-(2-3)-O-β-D-galactopyranosyl-(1-3)-2-acetamido-2-deoxy-α-D-glucopyranose
  参考文献：
  名称：

  The use of porcine liver (2 → 3)-α-sialyltransferase in the large-scale synthesis of α-Neup5Ac-(2 → 3)-β-d-Galp-(1 → 3)-d-GlcpNAc, the epitope of the tumor-associated carbohydrate antigen CA 50

  摘要：

  Alpha-Neup5Ac-(2 --> 3)-beta-D-Galp-(1 --> 3)-D-GlcpNAc (2) and, alpha-Neup5Ac-(2 --> 3)-beta-D-Galp-(1 --> 3)-beta-D-GalpNAcOMBn were prepared on a large scale by the action of beta-D-Galp-(1 --> 3)-D-GalpNAc (2 --> 3)-alpha-sialyltransferase (partially purified from porcine liver) on beta-D-Galp-(1 --> 3)-D-GlcpNAc and beta-D-Galp-(1 --> 3)-beta-D-GlcpNAcOMBn, respectively. The trisaccharide 2 is the epitope of the tumor-associated carbohydrate antigen CA 50, highly expressed in human pancreatic adenocarcinoma.

  DOI：

  10.1016/s0008-6215(00)90555-x