benzyl 2-acetamido-3,6-di-O-benzoyl-2,4-dideoxy-4-fluoro-α-D-glucopyranoside | 290819-68-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl 2-acetamido-3,6-di-O-benzoyl-2,4-dideoxy-4-fluoro-α-D-glucopyranoside
• 英文别名: alpha-D-Glucopyranoside, phenylmethyl 2-(acetylamino)-2,4-dideoxy-4-fluoro-, 3,6-dibenzoate；[(2R,3S,4R,5R,6S)-5-acetamido-4-benzoyloxy-3-fluoro-6-phenylmethoxyoxan-2-yl]methyl benzoate
• CAS: 290819-68-0
• 化学式: C₂₉H₂₈FNO₇
• 分子量: 521.542
• InChiKey: KGDKOKWJAUETMI-CZECYLRVSA-N

物化性质

• 沸点：
  686.2±55.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于丙酮、氯仿

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  benzyl 2-acetamido-3,6-di-O-benzoyl-2,4-dideoxy-4-fluoro-α-D-glucopyranoside 在 palladium on activated charcoal 氢氧化钾 、 氢气 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 20.0 ℃ 、379.21 kPa 条件下， 反应 72.5h， 生成 2-acetamido-2,4-dideoxy-4-fluoro-α,β-D-glucopyranose
  参考文献：
  名称：

  Synthesis of 4-deoxy-4-fluoro analogues of 2-acetamido-2-deoxy-d-glucose and 2-acetamido-2-deoxy-d-galactose and their effects on cellular glycosaminoglycan biosynthesis

  摘要：

  4-Deoxy-4-fluoro analogues of 2-acetamido-2-deoxy-D-glucose and 2-acetamido-2-deoxy-D-galactose were synthesized and evaluated as inhibitors of hepatic glycosaminoglycan biosynthesis. 2-Acetamido-1,3,6-tri-O-acetyl-2,4-dideoxy-4-fluoro-D-glucopyranose (16) exhibited a reduction of [H-3]GlcN and [S-35]SO4 incorporation into hepatocyte cellular glycosaminoglycans to 12 and 18%, respectively, of the control cells, at 1.0 mM. Similarly, 2-acetamido-1,3,6-tri-O-acetyl-2,4-dideoxy-4-fluoro-D-gala (31) exhibited a reduction of [H-3]GlcN and [S-35]SO4 incorporation to 1 and 9%. respectively, of the control cells, at 1.0 mM. Unlike 16, 31 exhibited a reduction of [C-14]Leu incorporation into cellular protein to 57% of control cells, at 1.0 mM. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00049-5
• 作为产物：
  描述：

  苄基-2-乙酰胺基-2-脱氧-Alpha-D-吡喃葡萄糖苷 在 吡啶 、 二乙胺基三氟化硫 、 sodium nitrite 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.33h， 生成 benzyl 2-acetamido-3,6-di-O-benzoyl-2,4-dideoxy-4-fluoro-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of 4-deoxy-4-fluoro analogues of 2-acetamido-2-deoxy-d-glucose and 2-acetamido-2-deoxy-d-galactose and their effects on cellular glycosaminoglycan biosynthesis

  摘要：

  4-Deoxy-4-fluoro analogues of 2-acetamido-2-deoxy-D-glucose and 2-acetamido-2-deoxy-D-galactose were synthesized and evaluated as inhibitors of hepatic glycosaminoglycan biosynthesis. 2-Acetamido-1,3,6-tri-O-acetyl-2,4-dideoxy-4-fluoro-D-glucopyranose (16) exhibited a reduction of [H-3]GlcN and [S-35]SO4 incorporation into hepatocyte cellular glycosaminoglycans to 12 and 18%, respectively, of the control cells, at 1.0 mM. Similarly, 2-acetamido-1,3,6-tri-O-acetyl-2,4-dideoxy-4-fluoro-D-gala (31) exhibited a reduction of [H-3]GlcN and [S-35]SO4 incorporation to 1 and 9%. respectively, of the control cells, at 1.0 mM. Unlike 16, 31 exhibited a reduction of [C-14]Leu incorporation into cellular protein to 57% of control cells, at 1.0 mM. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00049-5

文献信息

• Ac34FGlcNAz is an effective metabolic chemical reporter for O-GlcNAcylated proteins with decreased S-glyco-modification
  作者：Jiajia Wang、Wei Cao、Wei Zhang、Biao Dou、Xueke Zeng、Shihao Su、Hongtai Cao、Xin Ding、Jing Ma、Xia Li

  DOI：10.1016/j.bioorg.2022.106139

  日期：2023.2

  O-GlcNAcylation is a ubiquitous post-translational modification governing vital biological processes in cancer, diabetes and neurodegeneration. Metabolic chemical reporters (MCRs) containing bio-orthogonal groups such as azido or alkyne, are widely used for labeling of interested proteins. However, most MCRs developed for O-GlcNAc modification are not specific and always lead to unexpected side reactions

  O-GlcNAcylation 是一种普遍存在的翻译后修饰，它控制着癌症、糖尿病和神经变性中的重要生物过程。含有叠氮基或炔烃等生物正交基团的代谢化学报告基因 (MCR) 被广泛用于标记感兴趣的蛋白质。然而，大多数为 O-GlcNAc 修饰开发的 MCR 并不特异，并且总是会导致意想不到的副反应，称为 S-糖修饰。在这里，我们尝试开发一种新的 Ac 3 4FGlcNAz MCR，用氟取代 Ac 4 GlcNAz 的 4-OH，以消除 GALE 的差向异构化并提高选择性。这些发现表明 Ac 34FGlcNAz 是一种强大的 O-GlcNAcylation 高效 MCR，该标记过程由 OGT 和 OGA 两种酶进行。最重要的是，Ac 3 4FGlcNAz 主要以 O-连接的形式掺入细胞内蛋白质并导致可忽略不计的 S-糖基修饰，表明它是 O-GlcNAcylation 的选择性 MCR。因此，我们认为这里开发的Ac
• 一种基于调控O-GlcNAc糖基化靶向CRPC的四价铂氨基己糖配合物及其应用
  申请人：河南大学

  公开号：CN116478227A

  公开（公告）日：2023-07-25

  本发明属于药物化学技术领域，具体涉及一种基于调控O‑GlcNAc糖基化靶向CRPC的四价铂氨基己糖配合物及其应用。本发明通过对化合物的结构进行设计，合成了轴向两侧拥有对称结构的四个四价铂氨基己糖配合物R3‑R6，以及轴向两侧拥有不对称结构的八个四价铂氨基己糖配合物R11‑R14、R16‑R19，通过将可干扰糖代谢的氟代乙酰氨基己糖对铂类药物进行糖基化修饰，在实现铂类药物靶向性的同时，调控HBP有效控制UDP‑GlcNAc底物浓度，从而降低细胞膜表面高分支N‑glycan，可以靶向CRPC并增强其对铂类药物的敏感性。本发明研究调控O‑GlcNAc糖基化靶向CRPC的四价铂氨基己糖配合物，不仅可以降低药物的毒副作用还可以改善药物的耐药性，提高药物在体内的富集水和活性。
• 一种基于调控Mucin型O-糖基化靶向CRPC的四价铂氨基己糖配合物及其应用
  申请人：河南大学

  公开号：CN116621900A

  公开（公告）日：2023-08-22

  本发明属于药物化学技术领域，具体涉及一种基于调控Mucin型O‑糖基化靶向CRPC的四价铂氨基己糖配合物及其应用。本发明通过对化合物的结构进行设计，合成了轴向两侧拥有不对称结构的四个四价铂氨基己糖配合物R7‑R10，以实现其活性好、毒性低的抗肿瘤疗效。本发明所述四价铂氨基己糖配合物对前列腺癌细胞具有较高的选择性，尤其是R10对雄激素非依赖性的前列腺癌细胞的杀伤作用达到纳摩尔级别。所述化合物R10在前列腺癌小鼠体内具有较高的抗肿瘤活性和抗转移能力，生物安全性高。氨基己糖类似物作为糖代谢药物研究的新趋势，通过将氨基己糖与药物进行缀合，发挥其双重功效的模式，成为研究者的重视。
• Synthesis of 4-deoxy-4-fluoro analogues of 2-acetamido-2-deoxy-d-glucose and 2-acetamido-2-deoxy-d-galactose and their effects on cellular glycosaminoglycan biosynthesis
  作者：Ali Berkin、Walter A. Szarek*、Robert Kisilevsky*

  DOI：10.1016/s0008-6215(00)00049-5

  日期：2000.6

  4-Deoxy-4-fluoro analogues of 2-acetamido-2-deoxy-D-glucose and 2-acetamido-2-deoxy-D-galactose were synthesized and evaluated as inhibitors of hepatic glycosaminoglycan biosynthesis. 2-Acetamido-1,3,6-tri-O-acetyl-2,4-dideoxy-4-fluoro-D-glucopyranose (16) exhibited a reduction of [H-3]GlcN and [S-35]SO4 incorporation into hepatocyte cellular glycosaminoglycans to 12 and 18%, respectively, of the control cells, at 1.0 mM. Similarly, 2-acetamido-1,3,6-tri-O-acetyl-2,4-dideoxy-4-fluoro-D-gala (31) exhibited a reduction of [H-3]GlcN and [S-35]SO4 incorporation to 1 and 9%. respectively, of the control cells, at 1.0 mM. Unlike 16, 31 exhibited a reduction of [C-14]Leu incorporation into cellular protein to 57% of control cells, at 1.0 mM. (C) 2000 Elsevier Science Ltd. All rights reserved.