p-Tolyl 4-O-benzoyl-2,3-di-O-benzyl-1-thio-β-L-fucopyranoside | 1607433-65-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-Tolyl 4-O-benzoyl-2,3-di-O-benzyl-1-thio-β-L-fucopyranoside
• 英文别名: p-Tolyl 4-O-benzoyl-2,3-di-O-benzyl-1-thio-beta-L-fucopyranoside；[(2S,3R,4R,5S,6R)-2-methyl-6-(4-methylphenyl)sulfanyl-4,5-bis(phenylmethoxy)oxan-3-yl] benzoate
• CAS: 1607433-65-7
• 化学式: C₃₄H₃₄O₅S
• 分子量: 554.707
• InChiKey: MOPLATOLPVNGOV-IWJFODQQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  40
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  79.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  p-Tolyl 4-O-benzoyl-2,3-di-O-benzyl-1-thio-β-L-fucopyranoside 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 水 、 丙酮 为溶剂， 反应 5.0h， 以25%的产率得到
  参考文献：
  名称：

  Stereoselective Synthesis of a Sulfated Tetrasaccharide Corresponding to a Rare Sequence in the Galactofucan Isolated from Sargassum polycystum

  摘要：

  The first chemical synthesis of a highly sulfated tetrasaccharide 1, as the rare sequence in the galactofucan isolated from the brown alga Sargassum polycystum, was achieved in a convergent and stereoselective manner. The key features of the synthetic strategy include construction of multiple contiguous 1,2-cis glycosidic bonds and [2 + 2] assembly based on the rationally developed D-galactose building block 6. The synthesized oligosaccharides were fully characterized using a combination of coupled-HSQC and other 2D NMR techniques.

  DOI：

  10.1021/jo500503r
• 作为产物：
  描述：

  苯甲酰氯 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以83%的产率得到p-Tolyl 4-O-benzoyl-2,3-di-O-benzyl-1-thio-β-L-fucopyranoside
  参考文献：
  名称：

  Stereoselective Synthesis of a Sulfated Tetrasaccharide Corresponding to a Rare Sequence in the Galactofucan Isolated from Sargassum polycystum

  摘要：

  The first chemical synthesis of a highly sulfated tetrasaccharide 1, as the rare sequence in the galactofucan isolated from the brown alga Sargassum polycystum, was achieved in a convergent and stereoselective manner. The key features of the synthetic strategy include construction of multiple contiguous 1,2-cis glycosidic bonds and [2 + 2] assembly based on the rationally developed D-galactose building block 6. The synthesized oligosaccharides were fully characterized using a combination of coupled-HSQC and other 2D NMR techniques.

  DOI：

  10.1021/jo500503r

文献信息

• Cancer Vaccines Based on Fluorine-Modified KH-1 Elicit Robust Immune Response
  作者：Yang Liu、Bohan Li、Xiujing Zheng、Decai Xiong、Xinshan Ye

  DOI：10.3390/molecules28041934

  日期：——

  KH-1 is a tumor-associated carbohydrate antigen (TACA), which serves as a valuable target of antitumor vaccines for cancer immunotherapies. However, most TACAs are thymus-independent antigens (TD-Ag), and they tend to induce immunological tolerance, leading to their low immunogenicity. To overcome these problems, some fluorinated derivatives of the KH-1 antigen were designed, synthesized, and conjugated to the carrier protein CRM197 to form glycoconjugates, which were used for immunological studies with Freund’s adjuvant. The results showed that fluorine-modified N-acyl KH-1 conjugates can induce higher titers of antibodies, especially IgG, which can recognize KH-1-positive cancer cells and can eliminate cancer cells through complement-dependent cytotoxicity (CDC). The trifluoro-modified KH-1-TF-CRM197 showed great potential as an anticancer vaccine candidate.

  KH-1 是一种肿瘤相关碳水化合物抗原（TACA），是抗肿瘤疫苗用于癌症免疫疗法的重要靶点。然而，大多数 TACA 都是胸腺依赖性抗原（TD-Ag），容易诱发免疫耐受，导致其免疫原性较低。为了克服这些问题，研究人员设计、合成了一些 KH-1 抗原的氟化衍生物，并将其与载体蛋白 CRM197 共轭形成糖共轭物，与弗罗因德佐剂一起用于免疫学研究。结果表明，氟修饰的 N-酰基 KH-1 结合物能诱导更高滴度的抗体，尤其是 IgG，它能识别 KH-1 阳性的癌细胞，并能通过补体依赖性细胞毒性（CDC）消灭癌细胞。三氟改性 KH-1-TF-CRM197 显示出作为抗癌疫苗候选物的巨大潜力。