1,2,3,4-tetra-O-benzoyl-α-D-fucopyranose | 197657-32-2

• 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: 1,2,3,4-tetra-O-benzoyl-α-D-fucopyranose
• 英文别名: (2R,3R,4S,5S,6R)-6-methyltetrahydro-2H-pyran-2,3,4,5-tetrayl tetrabenzoate；per-O-benzoyl-α-D-fucopyranose
• CAS: 197657-32-2
• 化学式: C₃₄H₂₈O₉
• 分子量: 580.591
• InChiKey: RLJCRSFLYYQNAK-SAOPXZSXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.27
• 重原子数：
  43.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  114.43
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  1,2,3,4-tetra-O-benzoyl-α-D-fucopyranose 在 palladium on activated charcoal 吡啶 、 甲醇 、 ammonium cerium(IV) nitrate 、 4 A molecular sieve 、 三氟化硼乙醚 、 四丁基溴化铵 、 氢溴酸 、 氢气 、 sodium methylate 、 氰化汞 、 二正丁基氧化锡 、 mercury dibromide 作用下， 以 乙醇 、 二氯甲烷 、 氯仿 、 乙酸乙酯 、 乙腈 为溶剂， 反应 100.58h， 生成 methyl 3-O-(3-O-methyl-β-D-fucopyranosyl)-β-D-quinovopyranoside
  参考文献：
  名称：

  Khatuntseva; Sherman; Shashkov, Russian Journal of Bioorganic Chemistry, 1997, vol. 23, # 3, p. 205 - 210

  摘要：

  DOI：
• 作为产物：
  描述：

  D-岩藻糖 、 苯甲酰氯 在 吡啶 、 4-二甲氨基吡啶 作用下， 以94%的产率得到1,2,3,4-tetra-O-benzoyl-α-D-fucopyranose
  参考文献：
  名称：

  Synthesis and cytotoxicity evaluation of natural α-bisabolol β-d-fucopyranoside and analogues

  摘要：

  alpha-Bisabolol beta-D-fucopyranoside, a cytotoxic naturally occurring compound, was efficiently synthesized along with five other alpha-bisabolol glycosides (beta-D-glucoside, beta-D-galactoside, alpha-D-mannoside, beta-D-Xyloside and alpha-L-rhamnoside). Glycosidation of ot-bisabolol was performed using Schmidt's inverse procedure and provided excellent yields (83-95%). Cytotoxicity was evaluated against a broad panel of cancerous cell lines including human and rat glioma (U-87, U-251 and GL-261) since the anticancer activity of alpha-bisabolol was previously demonstrated against brain tumor cell lines. The addition of a sugar moiety markedly increased alpha-bisabolol cytotoxicity in most cases. Among the synthesized glycosides, alpha-bisabolol alpha-L-rhamnopyranoside exhibited the strongest cytotoxic activity with IC50 ranging from 40 to 64 mu M. According to ADME in silico predictions, this glycoside closely respects physicochemical parameters necessary to cross the blood-brain barrier passively. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2008.11.013

文献信息

• Continuous nonradioactive method for screening trypanosomal trans-sialidase activity and its inhibitors
  作者：P. A. Sartor、R. Agusti、M. S. Leguizamon、O. Campetella、R. M. de Lederkremer

  DOI：10.1093/glycob/cwq056

  日期：2010.8.1

  Trypanosoma cruzi, the agent of American trypanosomiasis is unable to synthesize sialic acid (SA). Instead of using the corresponding nucleotide sugar as donor of the monosaccharide, the transfer occurs from α-2,3-linked SA in the host sialoglycoconjugates to terminal β-galactopyranosyl units of the parasite mucins. For that purpose, T. cruzi expresses a glycosylphosphatidylinositol-anchored trans-sialidase (TcTS) that is shed into the milieu, being detected in the blood during the acute phase of the infection. The essential role of TcTS in infection and the absence of a similar activity in mammals make this enzyme an attractive target for the development of alternative chemotherapies. However, there is no effective inhibitor toward this enzyme. In vitro, 3′-sialyllactose (SL) as donor and radioactive lactose as acceptor substrate are widely used to measure TcTS activity. The radioactive sialylated product is then isolated by anion exchange chromatography and measured. Here we describe a new nonradioactive assay using SL or fetuin as donor and benzyl β-d-Fuc-(1→6)-α-d-GlcNAc (1) as acceptor. Disaccharide 1 was easily synthesized by regioselective glycosylation of benzyl α-d-GlcNAc with tetra-O-benzoyl-d-fucose followed by debenzoylation. Compound 1 lacks the hydroxyl group at C-6 of the acceptor galactose and therefore is not a substrate for galactose oxidase. Our method relies on the specific quantification of terminal galactose produced by trans-sialylation from the donor to the 6-deoxy-galactose (D-Fuc) unit of 1 by a spectrophotometric galactose oxidase assay. This method may also discriminate sialidase and trans-sialylation activities by running the assay in the absence of acceptor 1.

  美洲锥虫病的病原体--克鲁斯锥虫无法合成硅铝酸（SA）。它不使用相应的核苷酸糖作为单糖的供体，而是从宿主唾液酸共轭物中的α-2,3-连接的 SA 转移到寄生虫粘蛋白的末端 β-半乳糖吡喃糖基单位。为此，克柔兹绦虫会表达一种糖基磷脂酰肌醇锚定的转硅烷酶（TcTS），这种酶会脱落到环境中，在感染的急性期会在血液中被检测到。TcTS 在感染中起着至关重要的作用，而哺乳动物体内没有类似的活性，因此这种酶成为开发替代化疗方法的一个有吸引力的靶点。然而，目前还没有针对这种酶的有效抑制剂。在体外，3′-半乳糖（SL）作为供体和放射性乳糖作为受体底物被广泛用于测量 TcTS 的活性。然后通过阴离子交换色谱法分离并测量放射性酰化产物。在此，我们介绍一种新的非放射性检测方法，它以 SL 或胎盘素为供体，以苄基 β-d-Fuc-(1→6)-α-d-GlcNAc (1) 为受体。通过对苄基 α-d-GlcNAc 与四-O-苯甲酰基-d-岩藻糖进行区域选择性糖基化，然后进行去苯甲酰化，可以轻松合成二糖 1。化合物 1 在接受半乳糖的 C-6 处缺少羟基，因此不是半乳糖氧化酶的底物。我们的方法是通过分光光度法半乳糖氧化酶测定法，对 1 的供体到 6-脱氧半乳糖（D-Fuc）单元的反糖苷化作用产生的末端半乳糖进行特异性定量。这种方法还可以在没有受体 1 的情况下进行检测，从而区分半乳糖苷酶和反式半乳糖苷化活性。
• α-bisabolol β-D-fucopyranoside as a potential modulator of β-amyloid peptide induced neurotoxicity: An in vitro & in silico study
  作者：Mahalingam Jeyakumar、Sethuraman Sathya、Soniya Gandhi、Prabhakarrao Tharra、Venkatesan Suryanarayanan、Sanjeev Kumar Singh、Beeraiah Baire、Kasi Pandima Devi

  DOI：10.1016/j.bioorg.2019.102935

  日期：2019.7

  strategy for the management of AD. In view of this, the present study was designed to synthesize and evaluate the multifunctional neuroprotective ability of the sesquiterpene glycoside α-bisabolol β-D-fucopyranoside (ABFP) against multiple targets like acetylcholinesterase, oxidative stress and β-amyloid peptide aggregation induced cytotoxicity. In silico computational docking and simulation studies

  阿尔茨海默氏病（AD）是影响老年人的多方面神经退行性疾病。对于AD治疗，现有药物无效，因为这些药物仅减轻疾病症状。由于AD的发展涉及多种病理蛋白，寻找针对多种AD蛋白的单个分子将是AD管理的新策略。有鉴于此，本研究旨在合成和评估倍半萜烯糖苷α-bisabololβ-D-岩藻糖苷（ABFP）对多个靶标如乙酰胆碱酯酶，氧化应激和β-淀粉样肽聚集诱导的细胞毒性的多功能神经保护能力。在计算机上用乙酰胆碱酯酶（AChE）对ABFP进行计算机对接和模拟研究表明，它可以与该酶的Asp74和Thr75残基相互作用。体外研究表明，该化合物除具有抗氧化，抗聚集和解聚特性外，还具有抑制AChE酶的显着能力。另外，分子动力学模拟研究证明Aβ肽和ABFP之间的相互作用残基被发现与Leu34和Ile31有关。此外，该化合物能够保护Neuro2 a细胞免受Aβ25-35肽诱导的毒性。总的来说，本研究显然证明了ABFP是
• Parasite glycoconjugates. Part 11.1 Preparation of phosphodisaccharide synthetic probes, substrate analogues for the elongating α-D-mannopyranosylphosphate transferase in the Leishmania
  作者：Andrew J. Ross、Irina A. Ivanova、Michael A. J. Ferguson、Andrei V. Nikolaev

  DOI：10.1039/b004653l

  日期：——

  A set of phosphodisaccharides, substrate analogues, which will be used to study acceptor–substrate specificity of the Leishmania biosynthetic enzymes, are synthesized using the Koenigs–Knorr and trichloroacetimidate methods for the glycosylation reactions, SN2 nucleophilic displacement of a triflic ester for epimerization, and the glycosyl hydrogenphosphonate method for phosphorylation.

  在糖基化反应中使用柯尼希斯康诺尔法和三氯乙酰亚氨酸法，在表聚反应中使用三氟丙烯酯的 SN2 亲核置换法，在磷酸化反应中使用糖基膦酸氢盐法，合成了一组磷酸二糖（底物类似物），用于研究利什曼原虫生物合成酶的受体底物特异性。
• Synthesis of 4-nitrophenyl β-d-fucofuranoside and β-d-fucofuranosyl-(1→3)-d-mannopyranose: modified substrates for studies on catalytic requirements of β-d-galactofuranosidase
  作者：Alejandro Chiocconi、Carla Marino、Rosa M de Lederkremer

  DOI：10.1016/s0008-6215(99)00241-4

  日期：1999.1

  of 4-nitrophenyl β- d -fucofuranoside ( 6 ) and β- d -fucofuranosyl-(1→3)- d -mannopyranose ( 10 ) are reported. These compounds, as analogues of galactofuranosides, were used for studying the influence of the hydroxyl group at C-6 in the interaction of the substrate with β- d -galactofuranosidase. For the synthesis of the fucofuranosides, 2,3,5-tri- O -benzoyl-6-bromo-6-deoxy- d -galactono-1,4-lactone

  摘要报道了4-硝基苯基β-d-呋喃呋喃糖苷（6）和β-d-呋喃呋喃糖基-（1→3）-d-甘露吡喃糖（10）的合成。这些化合物作为半呋喃呋喃糖苷的类似物，用于研究C-6处羟基在底物与β-d-半乳糖呋喃糖苷酶相互作用中的影响。对于岩藻呋喃糖苷的合成，2,3,5-三-O-苯甲酰基-6-溴-6-脱氧-d-半内酯-1,4-内酯（1）是关键中间体，其在还原内酯后基团与二异戊基硼烷，异头羟基的乙酰化以及溴在C-6处的催化氢解反应产生了1- O-乙酰基-2,3,5-三-O-苯甲酰基-α，β-d-呋喃呋喃糖（ 4），一种用于制备呋喃呋喃糖苷的方便衍生物。在SnCl 4存在下，将化合物4糖基化，或者用4-硝基苯酚制备6，或与2,5,6-三-O-苯甲酰基-d-甘露糖-1,4-内酯（7）一起通过糖基-醛内酯方法合成二糖10。为β-d-呋喃呋喃糖苷开发的合成途径既简单又有效。通过与来自倒青霉的外切β-d-半乳糖呋喃