2-aminoethyl 2-(acetamido)-2-deoxy-α-D-glucopyranoside | 851440-03-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-aminoethyl 2-(acetamido)-2-deoxy-α-D-glucopyranoside
• 英文别名: N-[(2S,3R,4R,5S,6R)-2-(2-aminoethoxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 851440-03-4
• 化学式: C₁₀H₂₀N₂O₆
• 分子量: 264.279
• InChiKey: QCTRCKYGWQLWGS-IGORNWKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  134
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-aminoethyl 2-(acetamido)-2-deoxy-α-D-glucopyranoside 、 alkaline earth salt of/the/ methylsulfuric acid 在 N-乙基吗啉 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 三乙基硅烷 作用下， 以 N,N-二甲基甲酰胺 、 三氟乙酸 为溶剂， 反应 13.0h， 生成 N'-[2-[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethyl]-N-[3-[2-[2-[3-[(4-hydrazinyl-4-oxobutanoyl)amino]propoxy]ethoxy]ethoxy]propyl]butanediamide
  参考文献：
  名称：

  Carbohydrate Microarrays for Assaying Galactosyltransferase Activity

  摘要：

  Carbohydrate microarrays have been used recently for the rapid analysis of glycan-protein or glycan-cell interactions and for the detection of pathogens. As a demonstration of its significance and versatility, the microarray technology has been applied in this effort to assay glycosyltransferase activities. In addition, carbohydrate microarray based methods have been employed to quantitatively determine binding affinities between lectins and carbohydrates.

  DOI：

  10.1021/ol070250l
• 作为产物：
  描述：

  [(2R,3S,4R,5R,6S)-5-acetamido-3,4-diacetyloxy-6-(2-bromoethoxy)oxan-2-yl]methyl acetate 在 palladium on activated charcoal sodium azide 、 氢气 、 sodium methylate 、 四丁基碘化铵 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 1.25h， 生成 2-aminoethyl 2-(acetamido)-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Carbohydrate Microarrays for Assaying Galactosyltransferase Activity

  摘要：

  Carbohydrate microarrays have been used recently for the rapid analysis of glycan-protein or glycan-cell interactions and for the detection of pathogens. As a demonstration of its significance and versatility, the microarray technology has been applied in this effort to assay glycosyltransferase activities. In addition, carbohydrate microarray based methods have been employed to quantitatively determine binding affinities between lectins and carbohydrates.

  DOI：

  10.1021/ol070250l

文献信息

• Novel bisubstrate uridine-peptide analogues bearing a pyrophosphate bioisostere as inhibitors of human O-GlcNAc transferase
  作者：Philip Ryan、Yun Shi、Mark von Itzstein、Santosh Rudrawar

  DOI：10.1016/j.bioorg.2021.104738

  日期：2021.5

  β-D-N-acetylglucosamine (O-GlcNAc) modification (O-GlcNAcylation), an essential post-translational as well as cotranslational modification, is the attachment of β-D-N-acetylglucosamine to serine and threonine residues of nucleocytoplasmic proteins. An aberrant O-GlcNAc profile on certain proteins has been implicated in metabolic diseases such as diabetes and cancer. Inhibitors of O-GlcNAc transferase (OGT) are valuable

  蛋白质O连接的 β-D- N-乙酰葡糖胺( O- GlcNAc) 修饰 ( O- GlcNAcylation) 是一种必不可少的翻译后和共翻译修饰，是 β-D- N-乙酰氨基葡萄糖与丝氨酸和苏氨酸残基的连接核质蛋白。某些蛋白质的异常O- GlcNAc 谱与代谢疾病如糖尿病和癌症有关。O- GlcNAc 转移酶 (OGT)抑制剂是研究蛋白O细胞生物学的重要工具-GlcNAc 修饰。在这项研究中，我们报告了新型尿苷肽缀合物分子，该分子由受体肽共价连接到催化失活的供体底物类似物上，该类似物带有焦磷酸盐生物等排体，并通过放射性 hOGT 测定探索它们对 OGT 的抑制活性。此外，我们通过分子建模研究了它们活动的结构基础，解释了它们对 OGT 抑制的缺乏效力。
• DRUG-LIGAND CONJUGATES, SYNTHESIS THEREOF, AND INTERMEDIATES THERETO
  申请人：Chen Zhiyu

  公开号：US20130190475A1

  公开（公告）日：2013-07-25

  The present invention relates to methods for synthesizing compounds of formula I or pharmaceutically acceptable salts thereof: I wherein each of X, Alk 1 , Alk 2 , and W are as defined and described herein.

  本发明涉及合成式I化合物或其药用可接受盐的方法：其中X、Alk1、Alk2和W各自如本文所定义和描述。
• Fabrication of Chemical Microarrays by Efficient Immobilization of Hydrazide-Linked Substances on Epoxide-Coated Glass Surfaces
  作者：Myung-ryul Lee、Injae Shin

  DOI：10.1002/anie.200462720

  日期：2005.5.6
• Synthetic assembly of α-O-linked-type GlcNAc using polymer chemistry affords sugar clusters, which effectively bind to lectins
  作者：Jyuichi Nakada、Takahiko Matsushita、Tetsuo Koyama、Ken Hatano、Koji Matsuoka

  DOI：10.1016/j.bmcl.2024.129616

  日期：2024.2
• US20140342980A1
  申请人：——

  公开号：US20140342980A1

  公开（公告）日：2014-11-20