allyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranose | 174851-20-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: allyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranose
• 英文别名: N-[(2S,4aR,6S,7R,8R,8aR)-8-hydroxy-2-phenyl-6-prop-2-enoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]acetamide
• CAS: 174851-20-8
• 化学式: C₁₈H₂₃NO₆
• 分子量: 349.384
• InChiKey: RZNDVHTWHYQMRO-ZXLDYLNASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.89
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  86.25
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  allyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranose 在 sodium methylate 、 氰化汞 、 溶剂黄146 作用下， 以 甲醇 、 硝基甲烷 、 苯 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：

  Allyl-2-acetamido-3,6-di-O-benzoyl-2-desoxy-α-D-galactopyranosid 在 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 生成 allyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranose
  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

文献信息

• Synthesis of allyl 3-deoxy- and 4-deoxy-β-D-galactopyranoside and simultaneous preparation of Gal(1 → 2)- and Gal(1 → 3)-linked disaccharide glycosides
  作者：Reiko T. Lee、Yuan C. Lee

  DOI：10.1016/0008-6215(94)84276-0

  日期：1994.1

  side were used. Attempts at the preparation of Gal(alpha, 1-->2)Gal and Gal(alpha, 1-->3)Gal disaccharide glycosides were made using the same strategy, but employing the 1-trichloro-acetimidate or 1-N-methylacetimidate of 2,3,4,6-tetra-O-benzyl-D-galactopyranose as the glycosyl donor. The latter imidate produced a mixture of Gal(alpha, 1-->2)Gal and Gal(alpha, 1-->3)Gal derivatives as major products

  报道了可用于探测半乳糖特异性凝集素的结合特异性的半乳糖衍生物的合成。这些包括烯丙基3-脱氧-和4-脱氧-β-D-xylo-己吡喃糖苷以及几种具有Gal（1-> 2）和Gal（1-> 3）键的二糖苷。使用2,3,4,6-四-O-乙酰基-α-D-吡喃半乳糖基溴化物作为糖基供体和烯丙基β-D-吡喃半乳糖苷的4,6-O-亚苄基衍生物制备β-连接的Gal二糖异构体，α-D-吡喃葡萄糖苷，α-D-甘露吡喃糖苷和2-乙酰氨基-2-脱氧-α-D-吡喃半乳糖苷作为受体。当使用甘露吡喃糖苷和2-乙酰氨基-2-脱氧半乳糖吡喃糖苷的亚苄基衍生物时，仅获得了Gal（1-> 3）-连接的二糖。尝试制备Gal（alpha，1-> 2）Gal和Gal（alpha，1-> 3）使用相同的策略制备Gal二糖苷，但是使用2,3,4,6-四-O-苄基-D-吡喃半乳糖的1-三氯-乙酰亚胺酸酯或1-N-甲基乙酰亚胺酸酯作为糖基供体。
• Synthesis and Evaluation of Glycoconjugates Comprising<i>N</i>-Acyl-Modified Thomsen-Friedenreich Antigens as Anticancer Vaccines
  作者：Shuang Sun、Xiu-Jing Zheng、Chang-Xin Huo、Chengcheng Song、Qin Li、Xin-Shan Ye

  DOI：10.1002/cmdc.201600094

  日期：2016.5.19

  BALB/c mice demonstrated that these modified TF antigen conjugates could stimulate the production of higher titers of IgG antibodies that cross‐reacted with native TF antigen. These glycoconjugates showed strong lymphocyte proliferative response, suggesting that they can induce cellular immunity. Furthermore, the elicited antisera reacted strongly with TF‐positive tumor cells (4T1). In particular, the N

  汤姆森-弗里登赖希（TF）抗原是一种重要的与肿瘤相关的碳水化合物抗原。然而，其低免疫原性限制了其在抗癌疫苗开发中的应用。为了解决这个问题，合成了几种N-酰基修饰的TF衍生物，并将其与载体蛋白CRM197（突变的白喉类毒素交叉反应物质）结合。BALB / c小鼠的免疫学结果表明，这些修饰的TF抗原缀合物可以刺激与天然TF抗原交叉反应的更高滴度的IgG抗体的产生。这些糖结合物表现出强烈的淋巴细胞增殖反应，表明它们可以诱导细胞免疫。此外，引起的抗血清与TF阳性肿瘤细胞（4T1）强烈反应。特别是N单氟乙酰基修饰的TF偶联物4 - CRM197对4T1细胞表现出最强的依赖补体的细胞毒性作用，这暗示了这种糖偶联物作为抗癌疫苗的潜力。
• 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。
• 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.