Globo-H pentenyl glycoside | 284663-02-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Globo-H pentenyl glycoside
• 英文别名: N-[(2S,3R,4R,5R,6R)-2-[(2R,3R,4S,5S,6R)-2-[(2R,3R,4R,5R,6S)-6-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-pent-4-enoxyoxan-3-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-4-[(2R,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 284663-02-1
• 化学式: C₄₃H₇₃NO₃₀
• 分子量: 1084.04
• InChiKey: OCOPCRDCRAOYAE-RFDKCXRNSA-N

物化性质

• 沸点：
  1330.5±65.0 °C(Predicted)
• 密度：
  1.65±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -9.2
• 重原子数：
  74
• 可旋转键数：
  21
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  484
• 氢给体数：
  18
• 氢受体数：
  30

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 Globo-H pentenyl glycoside 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 16.0h， 以4 mg的产率得到Globo-H pentenyl glycoside peracetate
  参考文献：
  名称：

  Linear Synthesis of the Tumor-Associated Carbohydrate Antigens Globo-H, SSEA-3, and Gb3

  摘要：

  The tumor-associated carbohydrate antigens Globo-H, SSEA-3, and Gb3 were synthesized in a linear fashion using glycosyl phosphate monosaccharide building blocks. All of the building blocks were prepared from readily available common precursors. The difficult alpha-(1-->4-cis)-galactosidic linkage was installed using a galactosyl phosphate donor with high selectivity. Introduction of the beta-galactosamine unit required the screening a variety of amine protecting groups to ensure good donor reactivity and protecting group compatibility. An N-trichloroacetyl-protected galactosamine donor performed best for the installation of the beta-glycosidic linkage. Conversion of the trichloroacetyl group to the N-acetyl group was achieved under mild conditions, fully compatible with the presence of multiple glycosidic bonds. This synthetic strategy is expected to be amenable to the synthesis of the globo-series of tumor antigens on solid-support.

  DOI：

  10.1021/jo025834+
• 作为产物：
  描述：

  D-吡喃葡萄糖 在 recombinant fucokinase 、 recombinant Haemophilus influenzae bifunctional β-1,3-N-acetylgalactosaminyltransferase 、 recombinant Helicobacter pylori α-1,2-fucosyltransferase 、 recombinant m Bifidobacterium longum N-acetylhexosamine 1- kinase 、 recombinant Meiothermus taiwanensis sp. nov. WR-220 galactokinase 、 recombinant uridine diphosphate-sugar pyrophosphorylase 、 C₁₀H₁₄N₅O₁₄P₃^(2-)*2Na⁽¹⁺⁾ 、 adenosine 5'-triphosphate disodium salt 、 magnesium chloride 、 manganese(ll) chloride 、 uridine 5'-triphosphate disodium 作用下， 以 aq. phosphate buffer 为溶剂， 反应 72.0h， 生成 Globo-H pentenyl glycoside
  参考文献：
  名称：

  Globo系列糖鞘脂的化学酶合成及其免疫抑制活性的评价

  摘要：

  一锅多酶糖基化方法能够使用共同底物 β-乳糖基鞘氨醇对包括 Gb4、Gb5、SSEA-4 和 Gbolo H 在内的 globo 系列鞘糖脂进行模块化组装，这有助于修饰神经酰胺骨架。Globo H 神经酰胺中的脂肪酸链长度显示出对 T 细胞活化的免疫抑制活性的差异。

  DOI：

  10.1002/asia.202200403

文献信息

• A Second Generation Synthesis of the MBr1 (Globo-H) Breast Tumor Antigen: New Application of then-Pentenyl Glycoside Method for Achieving Complex Carbohydrate Protein Linkages
  作者：Jennifer R. Allen、John G. Allen、Xu-Feng Zhang、Lawrence J. Williams、Andrzej Zatorski、Govindaswami Ragupathi、Philip O. Livingston、Samuel J. Danishefsky

  DOI：10.1002/(sici)1521-3765(20000417)6:8<1366::aid-chem1366>3.0.co;2-k

  日期：2000.4.17

  A new synthesis of the hexasaccharide MBr1 antigen (globo-H) is reported. A revised construction with improved efficiency was necessary because an anti-cancer vaccine containing this antigen is entering phase II and phase III clinical trials for prostate cancer. The key feature of this second generation synthesis is the preparation of globo-H as its n-pentenyl glycoside. This group serves as an anomeric

  报道了六糖MBr1抗原（globo-H）的新合成。由于含有这种抗原的抗癌疫苗正进入前列腺癌的II期和III期临床试验，因此有必要对结构进行改进以提高效率。第二代合成的关键特征是制备globo-H作为其正戊烯基糖苷。该基团用作端基保护基和用作与载体蛋白生物缀合的接头。所得的合成物允许产生适当量的globo-H用于临床试验。