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 | 333969-21-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 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
• CAS: 333969-21-4
• 化学式: C₄₂H₇₂N₄O₂₆S₂
• 分子量: 1113.18
• InChiKey: LPGHUWJKUWZMLG-WNQISASJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -7.3
• 重原子数：
  74
• 可旋转键数：
  29
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  521
• 氢给体数：
  17
• 氢受体数：
  28

反应信息

• 作为反应物：
  描述：

  1,6-己二胺 、 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 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 二甲基亚砜 为溶剂， 以50%的产率得到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]-N-[1-[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]-2-[6-[[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]hexylamino]-2-oxoethyl]propanamide
  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：

  allyl 2-acetamido-2-deoxy-3-O-(β-D-galactopyranosyl)-α-D-galactopyranoside 在 甲醇 、 偶氮二异丁腈 、 sodium methylate 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 29.0h， 生成 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
  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

文献信息

• Synthesis of <i>N</i>,<i>N</i>‘-bis(Acrylamido)acetic Acid-Based T-Antigen Glycodendrimers and Their Mouse Monoclonal IgG Antibody Binding Properties
  作者：René Roy、Myung-Gi Baek、Kate Rittenhouse-Olson

  DOI：10.1021/ja002596w

  日期：2001.3.1

  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.