methyl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonate-(2→6)-2-acetamido-2-deoxy-3,4-di-O-acetyl-1-O-(N-succinimidyl)-α-D-glactopyranoside | 381238-66-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonate-(2→6)-2-acetamido-2-deoxy-3,4-di-O-acetyl-1-O-(N-succinimidyl)-α-D-glactopyranoside
• CAS: 381238-66-0
• 化学式: C₃₆H₄₉N₃O₂₂
• 分子量: 875.792
• InChiKey: AQDDZMRAJQNGDF-MYIQQSKKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  61.0
• 可旋转键数：
  17.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  316.6
• 氢给体数：
  2.0
• 氢受体数：
  22.0

反应信息

• 作为反应物：
  描述：

  methyl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonate-(2→6)-2-acetamido-2-deoxy-3,4-di-O-acetyl-1-O-(N-succinimidyl)-α-D-glactopyranoside 在 吡啶 、 lithium iodide 作用下， 以96%的产率得到
  参考文献：
  名称：

  Sialyl-Tn Polysaccharide A1 as an Entirely Carbohydrate Immunogen: Synthesis and Immunological Evaluation

  摘要：

  Sialyl Thomsen-nouveau (STn) is a tumor-associated carbohydrate antigen (TACA) that is overexpressed hi a variety of carcinomas such as breast, ovarian, and colon cancer. In normal tissue, STn is not detectable, which is critical for opportunities in developing cancer immunotherapies. A novel, entirely carbohydrate, semisynthetic STn-polysaccharide (PS) A1 conjugate was prepared and evaluated in CS7BL/6 mice. STn-PS A1 was combined with commercially available monophosphoryl lipid A-based adjuvant, and after immunization, ELISA indicated a strong immune response for inducing anti STn IgM/IgG antibodies. The specificity of these antibodies was concomitantly investigated using FACS analysis, and the results indicated excellent cell surface binding events to STn-expressing cancer cell lines MCF-7 and OVCAR-5. An INF-gamma ELISpot assay was conducted to further confirm a robust cellular immunity invoked by STn-PS A1. Most importantly, the raised antibodies conferred complement-dependent cellular cytotoxicity against MCF-7 and OVCAR-5 cells.

  DOI：

  10.1021/jacs.6b05675
• 作为产物：
  描述：

  phenyl 2-azido-4-benzoyl-2-deoxy-1-thio-β-D-galactopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 sodium methylate 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 26.33h， 生成 methyl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonate-(2→6)-2-acetamido-2-deoxy-3,4-di-O-acetyl-1-O-(N-succinimidyl)-α-D-glactopyranoside
  参考文献：
  名称：

  Sialyl-Tn Polysaccharide A1 as an Entirely Carbohydrate Immunogen: Synthesis and Immunological Evaluation

  摘要：

  Sialyl Thomsen-nouveau (STn) is a tumor-associated carbohydrate antigen (TACA) that is overexpressed hi a variety of carcinomas such as breast, ovarian, and colon cancer. In normal tissue, STn is not detectable, which is critical for opportunities in developing cancer immunotherapies. A novel, entirely carbohydrate, semisynthetic STn-polysaccharide (PS) A1 conjugate was prepared and evaluated in CS7BL/6 mice. STn-PS A1 was combined with commercially available monophosphoryl lipid A-based adjuvant, and after immunization, ELISA indicated a strong immune response for inducing anti STn IgM/IgG antibodies. The specificity of these antibodies was concomitantly investigated using FACS analysis, and the results indicated excellent cell surface binding events to STn-expressing cancer cell lines MCF-7 and OVCAR-5. An INF-gamma ELISpot assay was conducted to further confirm a robust cellular immunity invoked by STn-PS A1. Most importantly, the raised antibodies conferred complement-dependent cellular cytotoxicity against MCF-7 and OVCAR-5 cells.

  DOI：

  10.1021/jacs.6b05675

文献信息

• Synthesis of Oxime-Linked Mucin Mimics Containing the Tumor-Related T_N and Sialyl T_N Antigens
  作者：Lisa A. Marcaurelle、Youngsook Shin、Scarlett Goon、Carolyn R. Bertozzi

  DOI：10.1021/ol0166247

  日期：2001.11.1

  [reaction--see text] The synthesis of oxime-linked mucin mimics was accomplished via the incorporation of multiple ketone residues into a peptide followed by reaction with aminooxy sugars corresponding to the tumor-related T(N) and sialyl T(N) (ST(N)) antigens.

  [反应-见正文]肟连接的粘蛋白模拟物的合成是通过将多个酮残基掺入肽中，然后与对应于肿瘤相关T（N）和唾液酸T（N）的氨氧基糖反应完成的（ ST（N））抗原。