allyl 2-acetamido-2-deoxy-3-O-(β-D-galactopyranosyl)-α-D-galactopyranoside | 110879-61-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2-acetamido-2-deoxy-3-O-(β-D-galactopyranosyl)-α-D-galactopyranoside
• 英文别名: allyl (β-D-galactopyranosyl)-(1→3)-2-acetamido-2-deoxy-α-D-galactopyranoside；Gal(b1-3)GalNAc(a)-O-allyl；N-[(2S,3R,4R,5R,6R)-5-hydroxy-6-(hydroxymethyl)-2-prop-2-enoxy-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]acetamide
• CAS: 110879-61-3
• 化学式: C₁₇H₂₉NO₁₁
• 分子量: 423.417
• InChiKey: UVYUNXFDFDXDBX-QASPSWGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  187
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  allyl 2-acetamido-2-deoxy-3-O-(β-D-galactopyranosyl)-α-D-galactopyranoside 在 偶氮二异丁腈 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 24.0h， 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：

  Simultaneous binding of mouse monoclonal antibody and streptavidin to heterobifunctional dendritic l -lysine core bearing T-antigen tumor marker and biotin

  摘要：

  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.

  DOI：

  10.1016/s0968-0896(01)00205-x
• 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 23.0h， 生成 allyl 2-acetamido-2-deoxy-3-O-(β-D-galactopyranosyl)-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 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。
• 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。
• Synthesis and cholera toxin binding properties of multivalent GM1 mimicsElectronic supplementary information (ESI) available: characterization of the polyvalent compounds ? imide by-products. See http://www.rsc.org/suppdata/ob/b4/b405344c/
  作者：Daniela Arosio、Ioannis Vrasidas、Paola Valentini、Rob M. J. Liskamp、Roland J. Pieters、Anna Bernardi

  DOI：10.1039/b405344c

  日期：——

  inhibition assay the prepared inhibitors showed good inhibition. While the monovalent GM1 mimic showed the expected inhibition in the 200 microM range the multivalent scaffolds led to increased binding. The tetravalent compound was shown to be 440-fold more potent than its monovalent counterpart. The octavalent analog, however, was the most potent compound as determined using an ELISA assay.

  基于3,5-二-（2-氨基乙氧基）-苯甲酸分支单元的树枝状大分子用于附着多个副本的GM1模拟物，以抑制霍乱毒素的结合。合成了高达八价的体系以及相关的参考化合物，在一种情况下，该参考化合物包含一价形式的配体，在另一种情况下包含支架但不包含配体。使用表面等离振子共振抑制测定法，所制备的抑制剂表现出良好的抑制作用。虽然单价GM1模拟物显示了200 microM范围内的预期抑制作用，但多价支架却导致结合增加。已显示该四价化合物的效力比其一价对应物高440倍。然而，八价类似物是用ELISA测定法测定的最有效的化合物。
• Design, Synthesis and Bioactivity of Core 1 O-glycan and its Derivative on Human Gut Microbiota
  作者：Huanhuan Qu、Baixue Li、Jingyi Yang、Huaiwen Liang、Meixia Li、Kan Ding

  DOI：10.2174/1570180816666181218143207

  日期：2019.11.8

  belonging to Bacteroidetes, a predominantphyla in the distal gut, as models to study the bioactivity of core 1 and its derivative on human gut microbiota. Results: According to our results, both core 1 and derivative could support the growth of B. fragilis, especially the core 1 derivative, while failed to support the growth of B. thetaiotaomicron and B. ovatus. Conclusion: This suggested that the

  背景：二糖核心1（Galβ1-3GalNAc）是自然界中常见的O-聚糖结构。生化研究证实，核心1结构的形成是O-聚糖生物合成的重要初始步骤，对人体具有重要意义。 目的：我们的研究将为O-聚糖的合成及其生物测定提供有意义和有用的见解。并且所有合成的糖苷将在开发用于寡糖构建的方案中用作中间构件。 方法：在本文中，我们首先使用化学方法制备了核心1及其衍生物，并有效地合成了一种新型的二糖。阐明了合成化合物的结构，并通过1 H NMR，13 C NMR和MS进行了确认。然后，我们采用属于拟杆菌科的三种人类肠道共生体（肠道远端的一种优势菌）作为模型来研究核心1及其衍生物对人类肠道菌群的生物活性。 结果：根据我们的结果，核心1和衍生物均可支持脆弱的芽孢杆菌的生长，尤其是核心1衍生物的生长，而不能支持thetaiotaomicron和卵形芽孢杆菌的生长。 结论：这表明脆弱的芽孢杆菌可能具有特异性的糖水解酶来切断糖苷键以获得单糖。