2-aminoethyl (β-D-galactopyranosyl)-(1->3)-2-acetamido-2-deoxy-α-D-galactopyranoside | 150195-14-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-aminoethyl (β-D-galactopyranosyl)-(1->3)-2-acetamido-2-deoxy-α-D-galactopyranoside
• 英文别名: Gal(b1-3)GalNAc(a)-O-EtNH2；N-[(2S,3R,4R,5R,6R)-2-(2-aminoethoxy)-5-hydroxy-6-(hydroxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]acetamide
• CAS: 150195-14-5
• 化学式: C₁₆H₃₀N₂O₁₁
• 分子量: 426.421
• InChiKey: FBMKQHJQWZJEMZ-KTZLHQQSSA-N

物化性质

• 沸点：
  796.2±60.0 °C(Predicted)
• 密度：
  1.53±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.6
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  213
• 氢给体数：
  8
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2-aminoethyl (β-D-galactopyranosyl)-(1->3)-2-acetamido-2-deoxy-α-D-galactopyranoside 、 Fluorescein isothiocyanate 在 碳酸氢钠 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 以100%的产率得到5-[2-[(2S,3R,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxyethylcarbamothioylamino]-2-(3-hydroxy-6-oxoxanthen-9-yl)benzoic acid
  参考文献：
  名称：

  Investigation of Nonspecific Effects of Different Dyes in the Screening of Labeled Carbohydrates against Immobilized Proteins

  摘要：

  Carbohydrates play an important role in life processes, and combinatorial chemistry can provide useful sources of thousands of synthetic carbohydrates as potential ligands for biological receptors. To accelerate the detection of positive hits arising from specific interactions between a carbohydrate and a protein, the use of fluorescent dyes can serve as a reliable detecting tool. A study of labeled carbohydrates to lectins conjugated to a solid-support shows that succinimidyl 6-(N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino)hexanoate (NBD-X) dye provides by far the lowest level of nonspecific interaction with immobilized protein. This observation is in stark contrast with the commonly used labeling reagents constituted of charged and aromatic groups, for instance, FITC and TAMRA dyes.

  DOI：

  10.1021/jo051503w
• 作为产物：
  描述：

  2-乙酰氨基-2-脱氧-D-吡喃半乳糖 在 palladium on activated charcoal 4 A molecular sieve 、 camphor-10-sulfonic acid 、 三氟化硼乙醚 、 氢气 、 sodium methylate 、 氰化汞 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 甲醇 、 硝基甲烷 、 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 43.0h， 生成 2-aminoethyl (β-D-galactopyranosyl)-(1->3)-2-acetamido-2-deoxy-α-D-galactopyranoside
  参考文献：
  名称：

  Investigation of Nonspecific Effects of Different Dyes in the Screening of Labeled Carbohydrates against Immobilized Proteins

  摘要：

  Carbohydrates play an important role in life processes, and combinatorial chemistry can provide useful sources of thousands of synthetic carbohydrates as potential ligands for biological receptors. To accelerate the detection of positive hits arising from specific interactions between a carbohydrate and a protein, the use of fluorescent dyes can serve as a reliable detecting tool. A study of labeled carbohydrates to lectins conjugated to a solid-support shows that succinimidyl 6-(N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino)hexanoate (NBD-X) dye provides by far the lowest level of nonspecific interaction with immobilized protein. This observation is in stark contrast with the commonly used labeling reagents constituted of charged and aromatic groups, for instance, FITC and TAMRA dyes.

  DOI：

  10.1021/jo051503w

文献信息

• Design, Synthesis, and Bioactivity Evaluation of a TF-Based Cancer Vaccine Candidate Using Lipid A Mimetics As a Built-In Adjuvant
  作者：Lingqiang Gao、Guiqi Li、Cuiping Qiu、Yifan Ye、Xiaohui Li、Pan Liao、Wenbo Ming、Zhongqiu Liu、Xiang Luo、Guochao Liao

  DOI：10.1021/acs.jmedchem.4c00042

  日期：2024.6.27

  This study describes the design and synthesis of five TF-based cancer vaccine candidates using a lipid A mimetic as the carrier and a built-in adjuvant. All synthesized conjugates elicited robust and consistent TF-specific immune responses in mice without external adjuvants. Immunological studies subsequently conducted in wild-type and TLR4 knockout C57BL/6 mice demonstrated that the activation of

  本研究描述了五种基于 TF 的癌症候选疫苗的设计和合成，使用脂质 A 模拟物作为载体和内置佐剂。所有合成的缀合物在没有外部佐剂的情况下都能在小鼠体内引发强烈且一致的 TF 特异性免疫反应。随后在野生型和 TLR4 敲除 C57BL/6 小鼠中进行的免疫学研究表明，TLR4 的激活是合成的脂质 A 模拟物增加 TF 特异性免疫反应的主要原因。所有由这些缀合物诱导的抗血清都可以特异性识别、结合并诱导 TF 阳性癌细胞的裂解。此外，代表性结合物2和3能够有效减少体内肿瘤的生长，延长小鼠的生存时间，且疗效优于明矾佐剂的糖蛋白TF-CRM197。因此，脂质 A 模拟物可能成为开发具有自我辅助特性的新型碳水化合物疫苗载体的有前途的平台，用于治疗癌症。