3,6-dioxaocta-1,8-diyl bis[β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside]

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,6-dioxaocta-1,8-diyl bis[β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside]
• 英文别名: 3,6-dioxaoct-1,8-diyl bis[β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside]；N-[(2R,3R,4R,5S,6R)-2-[2-[2-[2-[(2R,3R,4R,5S,6R)-3-acetamido-4-hydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxyethoxy]ethoxy]ethoxy]-4-hydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]acetamide
• 化学式: C₃₄H₆₀N₂O₂₄
• 分子量: 880.849
• InChiKey: AABWKIOCBKJHBC-FIHRMRRMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -8.9
• 重原子数：
  60
• 可旋转键数：
  21
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  393
• 氢给体数：
  14
• 氢受体数：
  24

反应信息

• 作为产物：
  描述：

  2,2',3,3',4',6,6'-七-O-乙酰基-alpha-D-乳糖基溴化物 在 三氟甲磺酸三甲基硅酯 、 叠氮基三甲基硅烷 、 碘 、 sodium methylate 、 溶剂黄146 、 锌 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 55.0h， 生成 3,6-dioxaocta-1,8-diyl bis[β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside]
  参考文献：
  名称：

  Synthesis of multivalent N-acetyl lactosamine modified quantum dots for the study of carbohydrate and galectin-3 interactions

  摘要：

  Ternary core/shell CdSeS/ZnS-QDs coated with N-acetyl lactosamine was prepared as a fluorescent probe to study the interactions of N-acetyl lactosamine and galectin-3. The synthesis of N-acetyl lactosamine was achieved through the 'azidoiodoglycosylation' method. The amount of ligand coated on QDs was determined by H-1 NMR and ICP-OES. The interactions between carbohydrates and galectin-3 were measured using SPR. The results revealed that the affinity of galectin-3 with di- and multivalent N-acetyl lactosamine increased 20 and 184-fold, respectively. The prepared glyco-QDs could be used as an efficient fluorescent probe to study carbohydrates and galectin-3 interactions. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.06.035

文献信息

• Synthesis and potential antimetastatic activity of monovalent and divalent β-d-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-d-glucopyranosides
  作者：Qing Li、Bin Su、Hui Li、Xiang-Bao Meng、Meng-Shen Cai、Zhong-Jun Li、Rou-Li Zhou、Ta-Lin Suo

  DOI：10.1016/s0008-6215(02)00438-x

  日期：2003.1

  Anomers of monovalent and divalent beta-D-galactopyranosyl-(1-->4)-2-acetamido-2-deoxy-D-gluco-pyranosides were synthesized under different glycosylation conditions, and evaluated for in vitro antimetastatic activity. Three compounds showed promising inhibitory effects on cancer cell attachment, spreading, migration, and invasion. (C) 2002 Elsevier Science Ltd. All rights reserved.