2,3,4,6-tetra-O-acetyl-α-L mannopyranosyl bromide | 61303-35-3

• 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-acetyl-α-L mannopyranosyl bromide
• 英文别名: 2,3,4,6-tetra-O-acetyl-alpha-L-mannopyranosyl bromide；[(2S,3S,4R,5R,6S)-3,4,5-triacetyloxy-6-bromooxan-2-yl]methyl acetate
• CAS: 61303-35-3
• 化学式: C₁₄H₁₉BrO₉
• 分子量: 411.203
• InChiKey: CYAYKKUWALRRPA-ODXJTPSBSA-N

物化性质

• 熔点：
  56-58 °C
• 沸点：
  412.0±45.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-acetyl-α-L mannopyranosyl bromide 在 lutidine 、 氨 、 sodium hydride 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 (3aR,5S,6S,7R,7aR)-6,7-Bis-benzyloxy-5-benzyloxymethyl-2-methoxy-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran
  参考文献：
  名称：

  分子内糖基化过程中的双重不对称诱导

  摘要：

  N-碘代琥珀酰亚胺激活由苯基 2,3,4-tri-O-benzyl-1-thio-α-L- 和 -D-mannopyranosides 构建的预先安排的糖苷，这些糖苷通过琥珀酰间隔物通过位置 6 连接到位置 3苄基 2-O-苯甲酰基-6-O-苄基-α-L-和-D-吡喃葡萄糖苷（6,3-预先排列的 L-Man/L-Glc、D-Man/D-Glc、L-Man/D -Glc 和 D-Man/L-Glc) 以 70-78% 的产率提供相应的 3,6'-琥珀酰桥连二糖 Man-(1→4)-Glc 的 α/β-混合物。分子内糖基化的非对映选择性与预先排列的糖苷的形貌特性无关（α-端基异构体在 L-Man/L-Glc 和 D-Man/D-Glc 中占主导地位），但取决于几何特性（β-端基异构体以 L-Man/D-Glc 和 D-Man/L-Glc 为主）。因此，在预先安排的糖苷的分子内糖基化过程中，双重不对称诱导是有效的。

  DOI：

  10.1002/(sici)1099-0690(199801)1998:1<163::aid-ejoc163>3.0.co;2-i
• 作为产物：
  描述：

  [(2S,3S,4R,5R,6S)-3,4,5-triacetyloxy-6-methylsulfanyloxan-2-yl]methyl acetate 生成 2,3,4,6-tetra-O-acetyl-α-L mannopyranosyl bromide
  参考文献：
  名称：

  POZSGAY, VINCE;JENNINGS, HAROLD J., J. ORG. CHEM., 53,(1988) N 17, C. 4042-4052

  摘要：

  DOI：

文献信息

• [EN] DI- AND TRI-CATIONIC GLYCOSYLATED ANTITUMOR ETHER LIPIDS, L-GUCOSYLATED GAELS AND RHAMNOSE-LINKED GAELS AS CYTOTOXIC AGENTS AGAINST EPITHELIAL CANCER CELLS AND CANCER STEM CELLS<br/>[FR] ETHERS LIPIDIQUES ANTITUMORAUX GLYCOSYLÉS DI- ET TRICATIONIQUES, GAEL L-GLYCOSYLÉS ET GAEL LIÉS À DU RHAMNOSE UTILISABLES EN TANT QU'AGENTS CYTOTOXIQUES DIRIGÉS CONTRE DES CELLULES ÉPITHÉLIALES CANCÉREUSES ET DES CELLULES SOUCHES CANCÉREUSES
  申请人：UNIV MANITOBA

  公开号：WO2015179983A1

  公开（公告）日：2015-12-03

  Glycosylated Antitumor Ether Lipids (GAELs) kill cancer cells by a nonapoptotic pathway which is an attractive strategy to avoid resistance. To further optimize the antitumor effect, we prepared various analogs of di-, and tri-cationic GAEL analogs differing in the nature of the sugar (D-giucose or L-glucose), the anomeric linkage as well as position of the glycerolipid moiety. The di- and tri-cationic GAELs were synthesized and their in vitro anticancer properties were evaluated against drug resistant and aggressively growing cancer cell lines derived from human breast, prostate, pancreatic and ovarian cancers. The most potent dicationic GAEL analogs were also studied against cancer stem cells obtained from breast BT 474, prostate DU145 and ovarian A2780cp cell lines. Our results indicate that the number of positive charges, the position of the amino substituents and the nature of the sugar have significant effects on the anticancer activities of these compounds. The most active analog kill 50% of the cells at concentration range of 0.5-5μΜ and 90% of the cells at the concentration of 1-10μΜ depending on type of cancer cells.

  糖基化抗肿瘤醚脂质（GAELs）通过一种非凋亡途径杀灭癌细胞，这是一种吸引人的策略，可以避免抗药性。为了进一步优化抗肿瘤效果，我们制备了不同的双-和三-阳离子GAEL类似物，其糖的性质（D-葡萄糖或L-葡萄糖）、缩醛键以及甘油脂类团的位置不同。合成了双-和三-阳离子GAEL类似物，并评估了它们对人类乳腺、前列腺、胰腺和卵巢癌衍生的耐药和快速生长的癌细胞系的体外抗癌性能。最有效的双阳离子GAEL类似物也针对从乳腺BT 474、前列腺DU145和卵巢A2780cp细胞系中获得的癌干细胞进行了研究。我们的结果表明，阳离子数量、氨基取代物的位置和糖的性质对这些化合物的抗癌活性有显著影响。最活跃的类似物在浓度范围为0.5-5μΜ时杀死50%的细胞，在浓度为1-10μΜ时杀死90%的细胞，具体取决于癌细胞类型。
• Synthesis of<i>α</i>-<scp>L</scp>-Mannopyranosyl-containing Disaccharides and Phenols as Substrates for the<i>α</i>-<scp>L</scp>-Mannosidase Activity of Commercial Naringinase
  作者：Sachiko Esaki、Akemi Ohishi、Akiko Katsumata、Naoko Sugiyama、Shintaro Kamiya

  DOI：10.1271/bbb.57.2099

  日期：1993.1

  In order to clarify the substrate specificity of the α-L-mannosidase activity of naringinase (Sigma), the following disaccharides and phenol glycosides were freshly prepared: methyl 2-O-(α-L-mannopyranosyl)­β-D-glucoside (1), methyl 3-O-(α-L-mannopyranosyl)-α-D-glucoside (2), methyl 4-O-(α-L-mannopyranosyl)-α-D-glucoside (3), methyl 5-O-(α-L-mannopyranosyl)-β-D-glucoside (4), methyl 6-O-(α-L-mannopyranosyl)-α-D­glucoside (5), 6-O-(α-L-mannpyranosyl)-D-galactose (6), p-nitrophenyl α-L-mannoside (7), and 4-methyl umbelliferone α-L-mannoside (8).These compounds, except for 3 and 5, were hydrolyzed with naringinase.

  为了阐明枳椇苷酶（Sigma）α-L-甘露糖苷酶活性的底物特异性，制备了以下几种二糖和酚苷的新鲜样品：甲基 2-O-(α-L-甘露吡喃糖基)­β-D-葡糖苷（1）、甲基 3-O-(α-L-甘露吡喃糖基)-α-D-葡糖苷（2）、甲基 4-O-(α-L-甘露吡喃糖基)-α-D-葡糖苷（3）、甲基 5-O-(α-L-甘露吡喃糖基)-β-D-葡糖苷（4）、甲基 6-O-(α-L-甘露吡喃糖基)-α-D­葡糖苷（5）、6-O-(α-L-甘露吡喃糖基)-D-半乳糖（6）、对硝基苯 α-L-甘露糖苷（7）和 4-甲基伞形酮 α-L-甘露糖苷（8）。除了 3 和 5 之外，这些化合物均能被枳椇苷酶水解。
• Replacing <scp>d</scp>-Glucosamine with Its <scp>l</scp>-Enantiomer in Glycosylated Antitumor Ether Lipids (GAELs) Retains Cytotoxic Effects against Epithelial Cancer Cells and Cancer Stem Cells
  作者：Makanjuola Ogunsina、Pranati Samadder、Temilolu Idowu、Gilbert Arthur、Frank Schweizer

  DOI：10.1021/acs.jmedchem.6b01773

  日期：2017.3.9

  retain the cytotoxic effects of the D-GAELs including the ability to kill BT-474 breast cancer stem cells (CSCs). When compared to adriamycin, cisplatin, and the anti-CSC agent salinomycin, L-GAELs display superior activity to kill cancer stem cells (CSCs). Mode of action studies indicate that L-GAELs like the D-GAELs kill cells via an apoptosis-independent mechanism that was not due to membranolytic

  我们描述了代谢惰性的基于l-氨基葡萄糖的糖基化抗肿瘤醚脂质（L-GAELs），该脂质保留了D-GAELs的细胞毒性作用，包括杀死BT-474乳腺癌干细胞（CSCs）的能力。与阿霉素，顺铂和抗CSC药物沙利霉素相比，L-GAEL具有杀死癌细胞干细胞（CSC）的优异活性。作用方式研究表明，像D-GAELs一样的L-GAELs通过细胞凋亡非依赖性机制杀死细胞，这不是由于膜溶解作用引起的。
• Insulin-like, and insulin-antagonistic, carbohydrate derivatives. The synthesis of aryl and aralkyl d-mannopyranosides and 1-thio-d-mannopyranosides
  作者：Philippe L. Durette、Tsung Y. Shen

  DOI：10.1016/s0008-6215(00)85657-8

  日期：1980.5

  of novel, aryl and aralkyl D-mannopyranosides and 1-thio-D-mannopyranosides were synthesized for evaluation of insulin-like and insulin-antagonistic properties. The substituted-phenyl alpha-D-mannopyranosides were prepared by the general procedure of Helferich and Schmitz-Hillebrecht, the substituted-phenyl 1-thio-alpha-D-mannopyranosides by a method corresponding to the Michael synthesis of aromatic

  合成了许多新颖的芳基和芳烷基D-甘露糖吡喃糖苷和1-硫代-D-甘露糖吡喃糖苷，用于评估胰岛素样和胰岛素拮抗性质。通过Helferich和Schmitz-Hillebrecht的通用方法制备取代的苯基α-D-甘露糖吡喃糖苷，通过对应于芳族糖苷的迈克尔合成的方法制备取代的苯基1-硫代α-D-甘露糖吡喃糖苷，以及芳烷基。通过2,3,4,6-四-O-乙酰基-1-硫代-α-D-甘露吡喃糖的芳烷基化作用制备1-硫代-α-D-甘露吡喃糖苷（15），然后进行O-脱乙酰化。通过将2-O-乙酰基-α-D反应的产物2-S-（四-O-乙酰基-α-D-甘露吡喃糖基）-2-thiopseudourea氢溴酸盐中的mid基进行碱性裂解，得到化合物15。 -甘露糖基溴与硫脲。苄基1-硫代-β-D-甘露吡喃糖苷
• METHOD FOR EVALUATING SPECIFIC INCORPORATION OF D-GLUCOSE INTO CELLS
  申请人：Yamada Katsuya

  公开号：US20110189708A1

  公开（公告）日：2011-08-04

  An object of the present invention is to provide a method for accurately evaluating the specific incorporation of D-glucose into cells. The present invention as a means for achieving the object is characterized by comprising contacting a D-glucose derivative that has a fluorescent chromophore in the molecule and is specifically incorporated into cells and an L-glucose derivative that has a fluorescent chromophore in the molecule with different cells in the same cell strain to be evaluated, respectively, comparing the fluorescence emitted by the D-glucose derivative that has a fluorescent chromophore in the molecule and is specifically incorporated into cells with the fluorescence emitted by the L-glucose derivative that has a fluorescent chromophore in the molecule, and evaluating the specific incorporation of D-glucose into cells relative to L-glucose by taking the difference between the two kinds of fluorescence intensities.

  本发明的目的是提供一种准确评估D-葡萄糖进入细胞的特定结合的方法。本发明的手段是通过将具有荧光色团的D-葡萄糖衍生物和具有荧光色团的L-葡萄糖衍生物与同一细胞系的不同细胞接触，分别比较具有荧光色团的D-葡萄糖衍生物和特定结合到细胞中的荧光强度与具有荧光色团的L-葡萄糖衍生物的荧光强度，并通过两种荧光强度的差异来评估D-葡萄糖相对于L-葡萄糖的特定结合到细胞中的情况。