bis[N,N'-(2-(2-aminoethyl)thioethylamido)]acetate | 333969-20-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: bis[N,N'-(2-(2-aminoethyl)thioethylamido)]acetate
• CAS: 333969-20-3
• 化学式: C₁₃H₂₆N₄O₄S₂
• 分子量: 366.506
• InChiKey: RXISVEBMODWQDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.12
• 重原子数：
  23.0
• 可旋转键数：
  13.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  136.54
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  bis[N,N'-(2-(2-aminoethyl)thioethylamido)]acetate 、 2,2-bis[3-[3-[(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]oxypropylsulfanyl]propanoylamino]acetic acid 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二甲基亚砜 为溶剂， 以55%的产率得到methyl 2,2-bis[3-[2-[[2,2-bis[3-[3-[(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]oxypropylsulfanyl]propanoylamino]acetyl]amino]ethylsulfanyl]propanoylamino]acetate
  参考文献：
  名称：

  Synthesis of N,N‘-bis(Acrylamido)acetic Acid-Based T-Antigen Glycodendrimers and Their Mouse Monoclonal IgG Antibody Binding Properties

  摘要：

  Novel glycodendrimers based on N,N'-bis(acrylamido)acetic acid core with valencies between two and six were synthesized. The breast cancer-associated T-antigen carbohydrate marker, (beta -Gal-(1 -3)-alpha -GalNAc-OR), was then conjugated by (i) 1,4-conjugate addition of thiolated T-antigen to the N-acrylamido dendritic cores and by (ii) amide bond formation between an acid derivative of the T-antigen and the polyamino dendrimers. The protein-binding ability of these new glycodendrimers was fully demonstrated by turbidimetric analysis and by enzyme-linked immunosorbent assay (ELISA) using peanut lectin from Arachis hypogaea and a mouse monoclonal antibody (MAb) FAA-J11 (IgG3). When tested as inhibitors of binding between: MAb and a polymeric form of the T-antigen (T-antigen-co-polyacrylamide) used as a coating antigen, di(17), tetra- (20), hexa- (21.), and tetravalent (22) dendrimers showed IC50 values of 174, 19, 48, and 18 nM, respectively. Two tetramers showed 120- to similar to 128-fold increased inhibitory properties over the monovalent antigen 6 used as a standard (IC50 2.3 mM). Heterobifunctional glycodendrimer bearing a biotin probe was also prepared for cancer cell labeling.

  DOI：

  10.1021/ja002596w
• 作为产物：
  描述：

  二[(1-氧代-2-丙烯基)氨基]-乙酸 在 氯化亚砜 、 N,N-二异丙基乙胺 作用下， 以 甲醇 为溶剂， 反应 10.0h， 生成 bis[N,N'-(2-(2-aminoethyl)thioethylamido)]acetate
  参考文献：
  名称：

  Synthesis of N,N‘-bis(Acrylamido)acetic Acid-Based T-Antigen Glycodendrimers and Their Mouse Monoclonal IgG Antibody Binding Properties

  摘要：

  Novel glycodendrimers based on N,N'-bis(acrylamido)acetic acid core with valencies between two and six were synthesized. The breast cancer-associated T-antigen carbohydrate marker, (beta -Gal-(1 -3)-alpha -GalNAc-OR), was then conjugated by (i) 1,4-conjugate addition of thiolated T-antigen to the N-acrylamido dendritic cores and by (ii) amide bond formation between an acid derivative of the T-antigen and the polyamino dendrimers. The protein-binding ability of these new glycodendrimers was fully demonstrated by turbidimetric analysis and by enzyme-linked immunosorbent assay (ELISA) using peanut lectin from Arachis hypogaea and a mouse monoclonal antibody (MAb) FAA-J11 (IgG3). When tested as inhibitors of binding between: MAb and a polymeric form of the T-antigen (T-antigen-co-polyacrylamide) used as a coating antigen, di(17), tetra- (20), hexa- (21.), and tetravalent (22) dendrimers showed IC50 values of 174, 19, 48, and 18 nM, respectively. Two tetramers showed 120- to similar to 128-fold increased inhibitory properties over the monovalent antigen 6 used as a standard (IC50 2.3 mM). Heterobifunctional glycodendrimer bearing a biotin probe was also prepared for cancer cell labeling.

  DOI：

  10.1021/ja002596w