(2R,4R,5S,6S)-5-acetamido-2-((2R,3S,4R,5R,6R)-3-((2S,4R,5R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-6-((2S,3R,4R,5S,6R)-3-acetamido-6-(((2R,4S,5R,6R)-5-acetamido-2-carboxy-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxypropyl)tetrahydro-2H-pyran-2-yloxy)methyl)-2-((2R,3S,4S,5R,6R)-3,5-dihydroxy-2-(hydroxymethyl)-6-(5-(3-mercaptopropanamido)pentyloxy)tetrahydro-2H-pyran-4-yloxy)-5-hydroxytetrahydro-2H-pyran-4-yloxy)-5-hydroxy-2-(hydroxymethyl)tetrahydro-2H-pyran-4-yloxy)-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxypropyl)tetrahydro-2H-pyran-2-carboxylic acid | 1447701-04-3

• 分子结构分类: 有机化合物 - 有机聚合物 - 多糖
• 英文名称: (2R,4R,5S,6S)-5-acetamido-2-((2R,3S,4R,5R,6R)-3-((2S,4R,5R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-6-((2S,3R,4R,5S,6R)-3-acetamido-6-(((2R,4S,5R,6R)-5-acetamido-2-carboxy-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxypropyl)tetrahydro-2H-pyran-2-yloxy)methyl)-2-((2R,3S,4S,5R,6R)-3,5-dihydroxy-2-(hydroxymethyl)-6-(5-(3-mercaptopropanamido)pentyloxy)tetrahydro-2H-pyran-4-yloxy)-5-hydroxytetrahydro-2H-pyran-4-yloxy)-5-hydroxy-2-(hydroxymethyl)tetrahydro-2H-pyran-4-yloxy)-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxypropyl)tetrahydro-2H-pyran-2-carboxylic acid
• CAS: 1447701-04-3
• 化学式: C₅₈H₉₇N₅O₃₈S
• 分子量: 1504.48
• InChiKey: KPPXPXDYKUBDTP-VIRPAACPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -13.48
• 重原子数：
  102.0
• 可旋转键数：
  35.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  674.77
• 氢给体数：
  25.0
• 氢受体数：
  37.0

反应信息

• 作为产物：
  描述：

  3,3'-dithiobis(sulfosuccinimidyl-propionate) sodium salt 、 (2R,4R,5S,6S)-5-acetamido-2-((2R,3S,4R,5R,6R)-3-((2S,3R,4R,5R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-6-((2S,3R,4R,5S,6R)-3-acetamido-6-(((2R,4S,5R,6R)-5-acetamido-2-carboxy-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxypropyl)tetrahydro-2H-pyran-2-yloxy)methyl)-2-((2R,3R,4S,5S,6R)-2-(5-aminopentyloxy)-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yloxy)-5-hydroxytetrahydro-2H-pyran-4-yloxy)-5-hydroxy-2-(hydroxymethyl)tetrahydro-2H-pyran-4-yloxy)-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxypropyl)tetrahydro-2H-pyran-2-carboxylic acid 在 1,4-二巯基-2,3-丁二醇 作用下， 以 aq. phosphate buffer 为溶剂， 反应 1.5h， 以78%的产率得到(2R,4R,5S,6S)-5-acetamido-2-((2R,3S,4R,5R,6R)-3-((2S,4R,5R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-6-((2S,3R,4R,5S,6R)-3-acetamido-6-(((2R,4S,5R,6R)-5-acetamido-2-carboxy-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxypropyl)tetrahydro-2H-pyran-2-yloxy)methyl)-2-((2R,3S,4S,5R,6R)-3,5-dihydroxy-2-(hydroxymethyl)-6-(5-(3-mercaptopropanamido)pentyloxy)tetrahydro-2H-pyran-4-yloxy)-5-hydroxytetrahydro-2H-pyran-4-yloxy)-5-hydroxy-2-(hydroxymethyl)tetrahydro-2H-pyran-4-yloxy)-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxypropyl)tetrahydro-2H-pyran-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and Vaccine Evaluation of the Tumor-Associated Carbohydrate Antigen RM2 from Prostate Cancer

  摘要：

  We have successfully developed a [1+2+3] one-pot strategy to synthesize the RM2 antigen hexasaccharide that was proposed to be a prostate tumor antigen. The structure of the synthetic product was verified by NMR analysis and antibody binding assay using a glycan microarray. In addition, the synthetic antigen was conjugated to a mutated diphtheria toxin (DT, CRM197) with different copy numbers and adjuvant combinations to form the vaccine candidates. After vaccination in mice, we used glycan microarrays to monitor their immune response, and the results indicated that, when one molecule of DT was incorporated with 4.7 molecules of RM2 on average (DT-RM4.7) and adjuvanted with the glycolipid C34, the combination exhibited the strongest anti-RM2 IgG titer. Moreover, the induced mouse antibodies mediated effective complement-dependent cytotoidcity (CDC) against the prostate cancer cell line LNCap.

  DOI：

  10.1021/ja403609x