methyl 2-O-acetyl-3-O-β-D-galactopyranosyl-β-D-galactopyranoside | 191486-25-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-O-acetyl-3-O-β-D-galactopyranosyl-β-D-galactopyranoside
• 英文别名: Gal(b1-3)b-Gal1Me2Ac；[(2R,3R,4S,5S,6R)-5-hydroxy-6-(hydroxymethyl)-2-methoxy-4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl] acetate
• CAS: 191486-25-6
• 化学式: C₁₅H₂₆O₁₂
• 分子量: 398.364
• InChiKey: XHXOMVBCNCPVLR-JYHXHQBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.1
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  185
• 氢给体数：
  6
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  methyl 2-O-acetyl-3-O-β-D-galactopyranosyl-β-D-galactopyranoside 在 porcine liver (2->3)-α-sialyltransferase on SP-C50 Sephadex 硫酸 、 sodium cacodylate 、 乙酸酐 、 sodium chloride 、 Triton X-100 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 168.0h， 生成 O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2-3)-D-galactopyranose
  参考文献：
  名称：

  Porcine liver (2 → 3)-α-sialyltransferase: substrate specificity studies and application of the immobilized enzyme to the synthesis of various sialylated oligosaccharide sequences

  摘要：

  In search of substrate analogues for the porcine liver beta-D-Galp-(1 --> 3)-D-Galp-NAc: CMP-Neu5Ac-(2 --> 3')-alpha-sialyltransferase, three disaccharides beta-D-Galp-(1 --> 3)-beta-D-Galp-O-CH3 (5), beta-D-Galp-(1 --> 3)-beta-D-(2-OAc)-Galp-O-CH3 (7) and beta-D-Galp-(1 --> 3)-beta-D-(2-OAc)-Galp-O-Bn (11) were synthesized and tested with the enzyme. Disaccharide 7 turned out to be a very good substrate allowing a rapid access to the trisaccharide alpha-Neu5Ac-(2 --> 3)-beta-D-Galp-(1 --> 3)-P-D-(2-OAc)-Galp-O-CH3 (13) on a preparative scale using the crude enzyme immobilized on cationic exchanger. Trisaccharide 13 was further exploited, first as a sialyl donor in Trypanosoma cruzi trans-sialidase catalyzed reaction and second through acetolysis reaction as a source for the synthon alpha-Neu5Ac-(2 --> 3)-D-Gal (16). (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00043-8
• 作为产物：
  描述：

  Gal2Ac3Ac4Ac6Ac(b1-3)b-Gal1Me2Ac4Ac6Ac 在 水 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以76%的产率得到methyl 2-O-acetyl-3-O-β-D-galactopyranosyl-β-D-galactopyranoside
  参考文献：
  名称：

  Porcine liver (2 → 3)-α-sialyltransferase: substrate specificity studies and application of the immobilized enzyme to the synthesis of various sialylated oligosaccharide sequences

  摘要：

  In search of substrate analogues for the porcine liver beta-D-Galp-(1 --> 3)-D-Galp-NAc: CMP-Neu5Ac-(2 --> 3')-alpha-sialyltransferase, three disaccharides beta-D-Galp-(1 --> 3)-beta-D-Galp-O-CH3 (5), beta-D-Galp-(1 --> 3)-beta-D-(2-OAc)-Galp-O-CH3 (7) and beta-D-Galp-(1 --> 3)-beta-D-(2-OAc)-Galp-O-Bn (11) were synthesized and tested with the enzyme. Disaccharide 7 turned out to be a very good substrate allowing a rapid access to the trisaccharide alpha-Neu5Ac-(2 --> 3)-beta-D-Galp-(1 --> 3)-P-D-(2-OAc)-Galp-O-CH3 (13) on a preparative scale using the crude enzyme immobilized on cationic exchanger. Trisaccharide 13 was further exploited, first as a sialyl donor in Trypanosoma cruzi trans-sialidase catalyzed reaction and second through acetolysis reaction as a source for the synthon alpha-Neu5Ac-(2 --> 3)-D-Gal (16). (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00043-8