N-[(2S,3R,4R,5R,6R)-5-Hydroxy-6-hydroxymethyl-2-(3-mercapto-propoxy)-4-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide | 333969-17-8

• 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)-5-Hydroxy-6-hydroxymethyl-2-(3-mercapto-propoxy)-4-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide
• CAS: 333969-17-8
• 化学式: C₁₇H₃₁NO₁₁S
• 分子量: 457.499
• InChiKey: SQILKGQRYOREPZ-QASPSWGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.91
• 重原子数：
  30.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  187.4
• 氢给体数：
  8.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  N-[(2S,3R,4R,5R,6R)-5-Hydroxy-6-hydroxymethyl-2-(3-mercapto-propoxy)-4-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-N-[4-[[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]butyl]pentanamide
  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：

  (2,3,4,6-tetra-O-benzoyl-α-D-galactopyranosyl)-(1-3)-2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside 在 甲醇 、 偶氮二异丁腈 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 26.0h， 生成 N-[(2S,3R,4R,5R,6R)-5-Hydroxy-6-hydroxymethyl-2-(3-mercapto-propoxy)-4-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide
  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

• Development of Clickable Monophosphoryl Lipid A Derivatives toward Semisynthetic Conjugates with Tumor-Associated Carbohydrate Antigens
  作者：Marcello Ziaco、Sabina Górska、Serena Traboni、Agnieszka Razim、Angela Casillo、Alfonso Iadonisi、Andrzej Gamian、Maria Michela Corsaro、Emiliano Bedini

  DOI：10.1021/acs.jmedchem.7b01234

  日期：2017.12.14

  obtain monophosphoryl lipid A derivatives equipped with clickable (azide, alkyne, double bond, or thiol precursor) moieties, starting from the native lipid A isolated from Escherichia coli, is presented. These lipid A derivatives can be conjugated with other interesting biomolecules, such as tumor-associated carbohydrate antigens (TACAs). In this way, the immunostimulant activity of monophosphoryl lipid

  从从大肠杆菌中分离的天然脂质A开始，获得具有可点击部分（叠氮基，炔烃，双键或硫醇前体）的单磷酰脂质A衍生物的半合成策略， 被表达。这些脂质A衍生物可以与其他有趣的生物分子，例如肿瘤相关的碳水化合物抗原（TACA）缀合。以这种方式，单磷酰基脂质A的免疫刺激活性可以显着改善TACA的免疫原性，从而为潜在的自佐剂抗癌疫苗候选者打开了大门。获得了单磷酰脂质A–Thomson-Friedenreich（TF）抗原偶联物，以证明该方法的可行性，该方法可作为最近报导于同一目标的高度复杂的全合成方法的一种有价值，快速且可扩展的选择。还报道了对该缀合物以及其他半合成脂质A衍生物的免疫活性的初步评估。
• Simultaneous binding of mouse monoclonal antibody and streptavidin to heterobifunctional dendritic l -lysine core bearing T-antigen tumor marker and biotin
  作者：Myung-Gi Baek、René Roy

  DOI：10.1016/s0968-0896(01)00205-x

  日期：2001.11

  Thiolated T-antigen [GalP-(1-3)-GalNAc alpha, T-Ag] (6), derived in situ from thioacetate 5 was coupled to N-chloroacetylated glycylglycyl L-lysine dendritic cores (7-9) using high yielding substitution reactions to afford di- (10), tetra- (11), and octa-valent (12) glycodendrimers in good yields (76-86%). Heterobifunctional conjugate 14 was prepared as a biosensor from tetravalent conjugate 11 and biotin hydrazide 13 using TBTU strategy. In a solid-phase double sandwich enzyme linked immunosorbent assays (ELISA), biotinylated conjugate 14 was shown to bind to streptavidin used as a coating material. Mouse Monoclonal anti T-Ag antibody (IgG3) and horseradish peroxydase-labeled goat anti mouse IgG, used for quantification, were found to bind T-Ag tetramer 14 immobilized on the surface of the streptavin layer. A typical saturation curve was observed for 14 while non-biotinylated tetramer 11 showed no binding in the entire concentration range. These results demonstrate the availability of both haptens toward the T-Ag antibody and streptavidin receptors. (C) 2001 Elsevier Science Ltd. All rights reserved.