p-Nitrophenyl 3-O-hydroxyethyl-β-L-fucoside | 183878-60-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-Nitrophenyl 3-O-hydroxyethyl-β-L-fucoside
• 英文别名: (2S,3R,4R,5S,6R)-4-(2-hydroxyethoxy)-2-methyl-6-(4-nitrophenoxy)oxane-3,5-diol
• CAS: 183878-60-6
• 化学式: C₁₄H₁₉NO₈
• 分子量: 329.307
• InChiKey: IIFQCVUALPPLNF-NIXGCWMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  134
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  p-Nitrophenyl 3-O-hydroxyethyl-β-L-fucoside 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 p-Aminophenyl 3-O-hydroxyethyl-β-L-fucoside
  参考文献：
  名称：

  Lectin-Mediated Drug Targeting: Discrimination of Carbohydrate-Mediated Cellular Uptake between Tumor and Liver Cells with Neoglycoconjugates Carrying Fucose Epitopes Regioselectively Modified in the 3-Position

  摘要：

  The circumvention of efficient "carbohydrate traps" in the liver is required for targeting glycoconjugates on tumor cells. As shown in the model system of bovine serum albumin (BSA) conjugates, the nature of R(1)-R(3) of the fucose epitope plays an important role in the discrimination of cellular uptake between tumor and liver cells as well as in the cytotoxic activity.

  DOI：

  10.1002/(sici)1521-3773(19991216)38:24<3680::aid-anie3680>3.0.co;2-9
• 作为产物：
  描述：

  2-硝基苯--Β-吡喃半乳糖苷 在 sodium tetrahydroborate 、 二正丁基氧化锡 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 生成 p-Nitrophenyl 3-O-hydroxyethyl-β-L-fucoside
  参考文献：
  名称：

  Lectin-Mediated Drug Targeting: Discrimination of Carbohydrate-Mediated Cellular Uptake between Tumor and Liver Cells with Neoglycoconjugates Carrying Fucose Epitopes Regioselectively Modified in the 3-Position

  摘要：

  The circumvention of efficient "carbohydrate traps" in the liver is required for targeting glycoconjugates on tumor cells. As shown in the model system of bovine serum albumin (BSA) conjugates, the nature of R(1)-R(3) of the fucose epitope plays an important role in the discrimination of cellular uptake between tumor and liver cells as well as in the cytotoxic activity.

  DOI：

  10.1002/(sici)1521-3773(19991216)38:24<3680::aid-anie3680>3.0.co;2-9

文献信息

• KOHLENHYDRATMODIFIZIERTE CYTOSTATIKA
  申请人：BAYER AG

  公开号：EP0819135B1

  公开（公告）日：1999-11-17
• US6271342B1
  申请人：——

  公开号：US6271342B1

  公开（公告）日：2001-08-07
• Lectin-Mediated Drug Targeting: Discrimination of Carbohydrate-Mediated Cellular Uptake between Tumor and Liver Cells with Neoglycoconjugates Carrying Fucose Epitopes Regioselectively Modified in the 3-Position
  作者：Hans-Georg Lerchen、Joerg Baumgarten、Norbert Piel、Victoria Kolb-Bachofen

  DOI：10.1002/(sici)1521-3773(19991216)38:24<3680::aid-anie3680>3.0.co;2-9

  日期：1999.12.16

  The circumvention of efficient "carbohydrate traps" in the liver is required for targeting glycoconjugates on tumor cells. As shown in the model system of bovine serum albumin (BSA) conjugates, the nature of R(1)-R(3) of the fucose epitope plays an important role in the discrimination of cellular uptake between tumor and liver cells as well as in the cytotoxic activity.