(2,3,4,6-tetra-O-benzoyl-α-D-galactopyranosyl)-(1-3)-2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside | 333969-14-5

• 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: (2,3,4,6-tetra-O-benzoyl-α-D-galactopyranosyl)-(1-3)-2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside
• 英文别名: allyl (2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1-3)-2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside；allyl (2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1→3)-2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside；[(2R,3S,4S,5R,6R)-6-[[(4aR,6S,7R,8R,8aR)-7-acetamido-2-phenyl-6-prop-2-enoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy]-3,4,5-tribenzoyloxyoxan-2-yl]methyl benzoate
• CAS: 333969-14-5
• 化学式: C₅₂H₄₉NO₁₅
• 分子量: 927.959
• InChiKey: ROTVBJNVMZHCHN-SOOLFCGRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  68
• 可旋转键数：
  20
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  190
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为反应物：
  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 sodium methylate 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 生成 allyl 2-acetamido-2-deoxy-3-O-(β-D-galactopyranosyl)-α-D-galactopyranoside
  参考文献：
  名称：

  Synthesis and antibody binding properties of glycodendrimers bearing the tumor related T-antigen

  摘要：

  乳腺癌标记物T抗原（Gal(β1-3)αGalNAc）被制备为丙烯基糖苷，随后转化为活性酯，并与一系列聚（酰胺胺）树枝状聚合物偶联，这些聚合物对小鼠单克隆IgG抗体具有强结合能力，且作为微孔板中有用的涂层抗原。

  DOI：

  10.1039/b008664i
• 作为产物：
  描述：

  D-GlcNAc 在 吡啶 、 三氟甲磺酸酐 、 三氟化硼乙醚 、 sodium methylate 、 zinc(II) chloride 作用下， 以 甲醇 、 硝基甲烷 、 二氯甲烷 、 氯仿 、 苯 为溶剂， 反应 21.0h， 生成 (2,3,4,6-tetra-O-benzoyl-α-D-galactopyranosyl)-(1-3)-2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside
  参考文献：
  名称：

  含T抗原的GlycoPAMAM树状大分子的合成和蛋白质结合特性。

  摘要：

  由相应的半乳糖基溴化物（6、7）和烯丙基以优异的产率制备烯丙基O-（β-D-吡喃半乳糖基）-（1-3）-2-乙酰氨基-2-脱氧-α-D-吡喃半乳糖苷（8）。使用Hg（CN）2作为促进剂的2-乙酰氨基-4,6-亚苄基-2-脱氧α-D-吡喃半乳糖苷（5）。化合物5是从N-乙酰基葡糖胺1获得的，其后继的保护基策略和C-4差向异构化是关键步骤。通过将3-巯基丙酸自由基加成到烯丙基二糖10中获得的羧酸官能化T抗原衍生物15，通过使用TBTU的有效酰胺偶联策略与PAMAM树突状核13-16偶联。以73％至99％的产率获得了具有4、8、16和32价（17-20）的T抗原残基的GlycoPAMAM树状聚合物。使用花生花生凝集素和小鼠单克隆IgG抗体证明了它们的蛋白质结合特性。较高价的结合物产生更强的结合相互作用，表明簇效应。这些g糖PAMAM缀合物对抗体-包被抗原相互作用的抑制潜力比单体T抗原残基的抑制潜力提高了3800倍（10）。

  DOI：

  10.1016/s0968-0896(01)00248-6

文献信息

• NEOGLYCOCONJUGATES AS VACCINES AND THERAPEUTIC TOOLS
  申请人：KORANEX CAPITAL

  公开号：US20210085770A1

  公开（公告）日：2021-03-25

  Neoglycoconjugates as immunogens and therapeutic/diagnostic tools are described herein. The neoglycoconjugates are produced by conjugating a carbohydrate antigen intermediate to a free amine group of a carrier material (e.g., carrier protein). The intermediate comprises a linker having a first end and a second end, the first end being conjugated to a carbohydrate antigen via a thio ether bond and the second end comprising a functional group reactable with a free amine group. Following coupling, the carbohydrate antigen becomes covalently bound to the carrier material via an amide, a carbamate, a sulfonamide, a urea, or a thiourea bond, thereby producing the neoglycoconjugate. Applications of the neoglycoconjugates as antigens, immunogens, vaccines, and in diagnostics are also described. Specifically, the use of (neo)glycoconjugates as vaccine candidates and other therapeutic tools against cancers, viruses such as SARS-CoV-2, and other diseases characterized by expression of aberrant glycosylation are also described.

  新糖基共轭物作为免疫原和治疗/诊断工具在此进行描述。这些新糖基共轭物是通过将碳水化合物抗原中间体与载体材料（例如载体蛋白质）的自由胺基结合而产生的。该中间体包括具有第一端和第二端的连接物，第一端通过硫醚键与碳水化合物抗原结合，第二端包括可与自由胺基反应的功能基团。在偶联后，碳水化合物抗原通过酰胺、碳酸酯、磺酰胺、脲或硫脲键与载体材料共价结合，从而产生新糖基共轭物。还描述了将新糖基共轭物用作抗原、免疫原、疫苗和诊断的应用。具体地，还描述了将（新）糖基共轭物用作疫苗候选物和其他治疗工具，用于对抗癌症、冠状病毒（例如SARS-CoV-2）等病毒以及其他表达异常糖基化的疾病。
• 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.
• Synthesis and antibody binding properties of glycodendrimers bearing the tumor related T-antigen
  作者：Myung-Gi Baek、René Roy、Kate Rittenhouse-Olson

  DOI：10.1039/b008664i

  日期：——

  Breast cancer marker T-antigen (Gal(β1-3)αGalNAc) was prepared as an allyl glycoside that was transformed into an active ester and coupled to a series of poly(amidoamine) dendrimers showing strong binding to mouse monoclonal IgG antibodies and serving as useful coating antigens in microtiter plates.

  乳腺癌标记物T抗原（Gal(β1-3)αGalNAc）被制备为丙烯基糖苷，随后转化为活性酯，并与一系列聚（酰胺胺）树枝状聚合物偶联，这些聚合物对小鼠单克隆IgG抗体具有强结合能力，且作为微孔板中有用的涂层抗原。
• Synthesis and protein binding properties of T-antigen containing GlycoPAMAM dendrimers
  作者：Myung-Gi Baek、René Roy

  DOI：10.1016/s0968-0896(01)00248-6

  日期：2002.1

  functionalized T-antigen derivative 15, obtained by radical addition of 3-mercaptopropionic acid to allyl disaccharide 10, was conjugated to PAMAM dendritic cores 13-16 by an efficient amide coupling strategy using TBTU. GlycoPAMAM dendrimers having T-antigen residues with 4, 8, 16 and 32 valencies (17-20) were obtained in 73 to 99% yields. Their protein binding properties were demonstrated using peanut

  由相应的半乳糖基溴化物（6、7）和烯丙基以优异的产率制备烯丙基O-（β-D-吡喃半乳糖基）-（1-3）-2-乙酰氨基-2-脱氧-α-D-吡喃半乳糖苷（8）。使用Hg（CN）2作为促进剂的2-乙酰氨基-4,6-亚苄基-2-脱氧α-D-吡喃半乳糖苷（5）。化合物5是从N-乙酰基葡糖胺1获得的，其后继的保护基策略和C-4差向异构化是关键步骤。通过将3-巯基丙酸自由基加成到烯丙基二糖10中获得的羧酸官能化T抗原衍生物15，通过使用TBTU的有效酰胺偶联策略与PAMAM树突状核13-16偶联。以73％至99％的产率获得了具有4、8、16和32价（17-20）的T抗原残基的GlycoPAMAM树状聚合物。使用花生花生凝集素和小鼠单克隆IgG抗体证明了它们的蛋白质结合特性。较高价的结合物产生更强的结合相互作用，表明簇效应。这些g糖PAMAM缀合物对抗体-包被抗原相互作用的抑制潜力比单体T抗原残基的抑制潜力提高了3800倍（10）。