6Az-GlcNAc 1-phosphate | 1166462-68-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6Az-GlcNAc 1-phosphate
• 英文别名: 6-azido-6-deoxy-N-acetylglucosamine-1-phosphate
• CAS: 1166462-68-5
• 化学式: C₈H₁₅N₄O₈P
• 分子量: 326.203
• InChiKey: UPWXDWWIFROMBX-FMDGEEDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.64
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  194.31
• 氢给体数：
  5.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  6Az-GlcNAc 1-phosphate 在 四氮唑 作用下， 以 吡啶 为溶剂， 反应 96.0h， 生成 UDP-6Az-GlcNAc monosodium salt
  参考文献：
  名称：

  6″-Azido-6″-deoxy-UDP-N-acetylglucosamine as a glycosyltransferase substrate

  摘要：

  6 ''-Azido-6 ''-deoxy-UDP-N-acetylglucosamine (UDP-6Az-GlcNAc) is a potential alternate substrate for N-acetylglucosaminyltransferases. This compound could be used to generate various glycoconjugates bearing an azide functionality that could in turn be subjected to further modification using Staudinger ligation or Huisgen cycloaddition. UDP-6Az-GlcNAc is synthesized from alpha-benzyl-N-acetylglucosaminoside in seven-steps with an overall yield of 6%. It is demonstrated to serve as a substrate donor for the glycosyl transfer reaction catalyzed by the human UDP-GlcNAc:polypeptidyltransferase (OGT) to the acceptor protein nucleoporin 62 (nup62). (c) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.090
• 作为产物：
  描述：

  在 四氮唑 、 ammonium hydroxide 作用下， 以 甲醇 、 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran 、 乙腈 为溶剂， 生成 6Az-GlcNAc 1-phosphate
  参考文献：
  名称：

  BISECTING-GLYCAN BRIDGED CONJUGATION FOR PRODUCING GLYCOPROTEIN CONJUGATES

  摘要：

  A bisecting glycan-bridged conjugation strategy that enables site-specific conjugation of glycoproteins without the need for chemical synthesis of oligosaccharide and amino acid engineering is disclosed. Application of this method is demonstrated by conjugation of human and mouse antibodies with a cytotoxin. This strategy preserves the Fc effector function of the antibodies and provides the ability to remodel glycans to fine-tune the immunogenicity and pharmacokinetic properties of antibody-drug conjugates through glycoengineering.

  公开号：

  WO2024102603A1

文献信息

• Changes in Metabolic Chemical Reporter Structure Yield a Selective Probe of <i>O</i>-GlcNAc Modification
  作者：Kelly N. Chuh、Balyn W. Zaro、Friedrich Piller、Véronique Piller、Matthew R. Pratt

  DOI：10.1021/ja504063c

  日期：2014.9.3

  Metabolic chemical reporters (MCRs) of glycosylation are analogues of monosaccharides that contain bioorthogonal functionalities and enable the direct visualization and identification of glycoproteins from living cells. Each MCR was initially thought to report on specific types of glycosylation. We and others have demonstrated that several MCRs are metabolically transformed and enter multiple glycosylation

  糖基化的代谢化学报告基因 (MCR) 是单糖的类似物，含有生物正交功能，能够直接可视化和识别活细胞中的糖蛋白。最初认为每个 MCR 报告特定类型的糖基化。我们和其他人已经证明，一些 MCR 会发生代谢转化并进入多种糖基化途径。因此，选择性 MCR 的开发仍然是一个未实现的关键目标。我们在此证明，6-叠氮基-6-脱氧-N-乙酰基-葡萄糖胺 (6AzGlcNAc) 是 O-GlcNAc 酰化蛋白的特异性 MCR。生化分析和 6AzGlcNAc、N-叠氮乙酰基-葡萄糖胺 (GlcNAz) 和 N-叠氮乙酰基-半乳糖胺 (GalNAz) 的比较蛋白质组学表明，6AzGlcNAc 专门标记细胞内蛋白质，而 GlcNAz 和 GalNAz 则掺入细胞内和细胞外/腔内糖蛋白的组合中。值得注意的是，6AzGlcNAc 不能通过需要 6-羟基磷酸化的经典挽救途径生物合成转化为相应的 UDP 糖供体。体外实验表明，6AzGlcNAc