2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl bromide | 60619-58-1

• 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-D-mannopyranosyl bromide
• 英文别名: [(2R,3R,4S,5S,6S)-3,4,5-triacetyloxy-6-bromooxan-2-yl]methyl acetate
• CAS: 60619-58-1
• 化学式: C₁₄H₁₉BrO₉
• 分子量: 411.203
• InChiKey: CYAYKKUWALRRPA-PEBLQZBPSA-N

物化性质

• 沸点：
  412.0±45.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(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-D-mannopyranosyl bromide 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以1.19 g的产率得到2-(乙酰氧基甲基)-6-叠氮基四氢-2H-吡喃-3,4,5-三基三乙酸酯
  参考文献：
  名称：

  CuAAC mediated synthesis of cyclen cored glycodendrimers of high sugar tethers at low generation

  摘要：

  DOI：

  10.1016/j.carres.2021.108403
• 作为产物：
  描述：

  β-D-mannopyranose pentaacetate 在 氢溴酸 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 生成 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl bromide
  参考文献：
  名称：

  CuAAC mediated synthesis of cyclen cored glycodendrimers of high sugar tethers at low generation

  摘要：

  DOI：

  10.1016/j.carres.2021.108403

文献信息

• Dynamic glycovesicle systems for amplified QCM detection of carbohydrate-lectin multivalent biorecognition
  作者：Eugene Mahon、Teodor Aastrup、Mihail Barboiu

  DOI：10.1039/b924766a

  日期：——

  We describe multivalent biorecognition of adsorbed lectin layers by biomimetic sensing nanoplatforms based on dynamic glycovesicles in a continuous flow QCM setup.

  我们描述了一种基于动态糖小泡的生物仿真传感纳米平台在连续流动QCM设置中对吸附的凝集素层进行多价生物识别的方法。
• Extension of the ring oxygen helicity rule to the phenyl- and phenyl-1-thio-glycosides
  作者：Katsunori Kohata、Toshio Konno、Hiroshi Meguro

  DOI：10.1016/0040-4039(80)80174-2

  日期：1980.1

  Circular Dichroism (CD) of the phenyl- and phenyl-1-thio-β(or α)-d-glycosides were studied. The sign and the rotational strength of Band C, the shortest and the strongest band between 180∼210 nm, were associated with the anomeric configuration and conformation in the same manner as the σ→σ* band of the ring oxygen in the 1-alkyl- and 1-alkyl-thio-glycosides. This result suggested that the ring oxygen

  研究了苯基和苯基-1-硫代β（或α）-d-糖苷的圆二色性（CD）。180〜210 nm之间最短和最强的能带C的符号和旋转强度与异头构型和构象相关联，其方式与1-烷基中环氧的σ→σ*带相同-和1-烷基-硫代糖苷。该结果表明，环氧螺旋度规则可以扩展到苯基-和苯基-1-硫代糖苷。
• Synthesis and anti-cancer activities of glycosides and glycoconjugates of diterpenoid isosteviol
  作者：Radmila R. Sharipova、Mayya G. Belenok、Bulat F. Garifullin、Anastasiya S. Sapunova、Alexandra D. Voloshina、Olga V. Andreeva、Irina Yu. Strobykina、Polina V. Skvortsova、Yuriy F. Zuev、Vladimir E. Kataev

  DOI：10.1039/c9md00242a

  日期：——

  A series of glycosides and glycoconjugates of diterpenoid isosteviol (16-oxo-ent-beyeran-19-oic acid) with various monosaccharide residues were synthesized and their cytotoxicity against some human cancer and normal cell lines was assayed. Most of the synthesized compounds demonstrated moderate to significant cytotoxicity against human cancer cell lines M-HeLa and MCF-7. Three lead compounds exhibited

  合成了一系列带有各种单糖残基的二萜异甜菊醇（16-oxoent-beyeran-19-oic Acid）的糖苷和糖缀合物，并测定了它们对某些人类癌症和正常细胞系的细胞毒性。大多数合成的化合物对人类癌细胞系 M-HeLa 和 MCF-7 表现出中度至显着的细胞毒性。三种先导化合物对 M-HeLa 表现出选择性细胞毒性活性（IC 50 = 10.0–15.1 μM），比抗癌药物他莫昔芬（IC 50 = 28.0 μM）的细胞毒性好三倍。此外，先导化合物对正常人Chang肝细胞系没有细胞毒性（IC 50 > 100 μM），而他莫昔芬抑制正常人Chang肝细胞的活力，IC 50值为46.0 μM。确定先导化合物的细胞毒性是由于诱导沿着线粒体途径进行的细胞凋亡。合成化合物的细胞毒活性基本上取决于单糖残基的性质及其位置，即单糖残基是直接连接到异甜菊醇骨架上还是通过多亚甲基连接体从其上移开。
• 一种含硫的化合物及其应用
  申请人：深圳华大生命科学研究院

  公开号：CN114075253B

  公开（公告）日：2023-09-08

  本发明公开了一种含硫的化合物及其应用。本发明提供了一种如式I所示的含硫的化合物，该类化合物水溶性好、膜透性好、且引入了两个硫化氢缓释结构具有更好的抗癌活性。
• Mannosylated Polyion Complexes for <i>In Vivo</i> Gene Delivery into CD11c⁺ Dendritic Cells
  作者：Lior Raviv、Michal Jaron-Mendelson、Ayelet David

  DOI：10.1021/mp5005492

  日期：2015.2.2

  Dendritic cells (DCs) possess unique abilities in initiating primary immune responses and thus represent prime targets for DNA-based vaccinations. Here, we describe the design and synthesis of mannosylated polyion complexes (PICs) composed of cationic polyethylenimine (PEI) and hydrophilic polyethylene glycol (PEG) segments, and bearing mono- and trivalent mannose as a ligand for targeting mannose receptor (MR/CD206)-positive DCs. Amino-terminated mannose (Man)-containing ligands in mono- and trivalent presentations (Man- and Man(3)-, respectively) were prepared and conjugated to PEG via an N-hydroxysuccinimide (NHS)-activated terminal. Thiolated PEI was conjugated to the mannosylated PEG via the maleimide (MAL)-activated terminal. The resulting positively charged diblock copolymers bearing mannoses (Man-PEG-b-PEI and Man3-PEG-b-PEI) were self-assembled with DNA to form PICs with lower surface charge than did their PEI building block and mean hydrodynamic diameters in the range of 100-450 nm, depending on the N/P ratio. Man3-PEG-b-PEI demonstrated a 3-4-fold greater transfection efficiency in MR-positive dendritic cell lines (THP-1, DC2.4), relative to Man-PEG-b-PEI, exhibited low cytotoxicity when compared with PEI, and showed low transfection efficiency in nondendritic HeLa cells. In preliminary in vivo experiments, Man-PEG-b-PEI/DNA and Man3-PEG-b-PEI/DNA demonstrated 2-3-fold higher gene delivery efficiency into CD11c+ DCs collected from inguinal lymph nodes of C57/BL6 mice, when compared to PEI/DNA complexes, as shown by GFP expression measurements, 24 h post subcutaneous injection. The results indicate that the mannosylated PICs are a safe and effective gene delivery system, showing in vivo specificity toward CD11c(+) DCs.