N-[(2S,3R,4R,5R,6R)-2-(2-Amino-ethoxy)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl]-acetamide | 107902-96-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[(2S,3R,4R,5R,6R)-2-(2-Amino-ethoxy)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl]-acetamide
• CAS: 107902-96-5
• 化学式: C₁₀H₂₀N₂O₆
• 分子量: 264.279
• InChiKey: QCTRCKYGWQLWGS-SPFKKGSWSA-N

物化性质

• 沸点：
  592.9±50.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.09
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  134.27
• 氢给体数：
  5.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  N-[(2S,3R,4R,5R,6R)-2-(2-Amino-ethoxy)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl]-acetamide 、 alkaline earth salt of/the/ methylsulfuric acid 在 N-乙基吗啉 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 三乙基硅烷 作用下， 以 N,N-二甲基甲酰胺 、 三氟乙酸 为溶剂， 反应 13.0h， 生成 N'-[2-[(2S,3R,4R,5R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethyl]-N-[3-[2-[2-[3-[(4-hydrazinyl-4-oxobutanoyl)amino]propoxy]ethoxy]ethoxy]propyl]butanediamide
  参考文献：
  名称：

  Carbohydrate Microarrays for Assaying Galactosyltransferase Activity

  摘要：

  Carbohydrate microarrays have been used recently for the rapid analysis of glycan-protein or glycan-cell interactions and for the detection of pathogens. As a demonstration of its significance and versatility, the microarray technology has been applied in this effort to assay glycosyltransferase activities. In addition, carbohydrate microarray based methods have been employed to quantitatively determine binding affinities between lectins and carbohydrates.

  DOI：

  10.1021/ol070250l
• 作为产物：
  描述：

  2-bromoethyl-2,3,4,6-tetra-O-acetyl-N-acetyl-α-D-galactosamine 在 palladium on activated charcoal sodium azide 、 氢气 、 sodium methylate 、 四丁基碘化铵 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 1.25h， 生成 N-[(2S,3R,4R,5R,6R)-2-(2-Amino-ethoxy)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl]-acetamide
  参考文献：
  名称：

  Carbohydrate Microarrays for Assaying Galactosyltransferase Activity

  摘要：

  Carbohydrate microarrays have been used recently for the rapid analysis of glycan-protein or glycan-cell interactions and for the detection of pathogens. As a demonstration of its significance and versatility, the microarray technology has been applied in this effort to assay glycosyltransferase activities. In addition, carbohydrate microarray based methods have been employed to quantitatively determine binding affinities between lectins and carbohydrates.

  DOI：

  10.1021/ol070250l

文献信息

• Full synthesis and bioactivity evaluation of Tn-RC-529 derivative conjugates as self-adjuvanting cancer vaccines
  作者：Lingqiang Gao、Qinghai Lian、Leilei Ma、Shiwei Su、Menglan Yang、Yuan Fang、Zhongqiu Liu、Xiang Luo、Guochao Liao

  DOI：10.1016/j.cclet.2021.03.046

  日期：2021.10

  and efficient strategy was established for the construction of RC-529 and its derivatives. Four conjugates of RC-529 derivatives with Tn antigen were synthesized and all elicited strong and T cell-dependent immune responses in mice without requiring external adjuvants. In addition, all antisera induced by these conjugates could specifically recognize, bind to and kill Tn-overexpressing cancer cells

  为构建RC-529及其衍生物建立了一种简便有效的策略。合成了四种RC-529衍生物与Tn抗原的结合物，它们均在小鼠中引起强力和T细胞依赖性免疫应答，而无需外部佐剂。此外，这些结合物诱导的所有抗血清都可以特异性识别，结合并杀死过表达Tn的癌细胞。因此，RC-529有望成为开发具有自我佐剂特性的新型疫苗载体以治疗癌症的有用平台。此外，初步的结构-活性关系分析为进一步优化RC-529和进一步研究RC-529提供了令人信服的支持。
• 一种含有单磷酸化的脂质A与糖抗原的缀合物及其制备方法和应用
  申请人：广州中医药大学（广州中医药研究院）

  公开号：CN111588847B

  公开（公告）日：2023-05-26

  本发明涉及一种含有单磷酸化的脂质A与糖抗原的缀合物及其制备方法和应用，属于抗肿瘤糖疫苗研制技术领域。本发明提供的一种含有单磷酸化的脂质A与糖抗原的缀合物，所述单磷酸化的脂质A与糖抗原的缀合物为通式为(Ⅰ)的化合物或其可药用盐。单磷酸化的脂质A能提高Tn糖抗原的免疫原性，将Tn糖抗原提呈到相应的免疫细胞，产生具有更高滴度的针对肿瘤糖抗原Tn特异性的免疫反应，因此该缀合物，作为全合成的糖抗原疫苗，有望成为新一代的抗肿瘤药物。
• Efficient Chemoenzymatic Synthesis of O-Linked Sialyl Oligosaccharides
  作者：Ola Blixt、Kirk Allin、Laura Pereira、Arun Datta、James C. Paulson

  DOI：10.1021/ja017881+

  日期：2002.5.1

  The tumor associated Tn (GalNAcalpha(1-1)-Thr/Ser)- and T (Galbeta(1-3)-GalNAcalpha(1-1)Thr/Ser)antigens and their sialylated derivatives are present on the surface of many cancer cells. Preparative synthesis of these sialylated T- and Tn-structures has been achieved mainly from a chemical synthetic approach due to the lack of the required glycosyltransferases. We demonstrate a flexible and efficient chemoenzymatic approach for using recombinant sialyltransferases including a chicken GalNAcalpha2,6-sialyltransferase (chST6GalNAc1) and a porcine Galbeta(1-3)GalNAcalpha-2,3-sialyltransferase (pST3Gal 1). Using these enzymes, the common O-linked sialosides Neu5Acalpha(2-6)GalNAcalpha(1-1)Thr, Galbeta(1-3)[Neu5Acalpha(26)]GalNAcalpha(1-1)Thr, Neu5Acalpha(2-3)Galbeta(1-3)GalNAcalpha(1-1)Thr, and Neu5Acalpha(2-3)Galbeta(1-3)[Neu5Acalpha(-26)]GalNAcalpha(1-1)Thr were readily prepared at preparative scale. The chST6GalNAc I was found to require at least one amino acid (Thr/Ser) for optimal activity, and is thus an ideal catalyst for synthesis of synthetic glycopeptides and glycoconjugates with O-linked glycans.