5-acetamido-3,5-dideoxy-D-glycero-D-galacto-2-nonulosonic acid

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-acetamido-3,5-dideoxy-D-glycero-D-galacto-2-nonulosonic acid
• 英文别名: N-acetyl-α-D-neuraminic acid；N-acetylneuraminic acid；sialic acid；5-Acetamido--3,5-dideoxy-D-glyceo-D-galacto-2-nonulosonic acid；(2R,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1S,2S)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• 化学式: C₁₁H₁₉NO₉
• 分子量: 309.273
• InChiKey: SQVRNKJHWKZAKO-USOVHJGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.5
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  177
• 氢给体数：
  7
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  正十七胺 、 5-acetamido-3,5-dideoxy-D-glycero-D-galacto-2-nonulosonic acid 在 N-羟基丁二酰亚胺 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Terminating the renewal of tumor-associated macrophages: A sialic acid-based targeted delivery strategy for cancer immunotherapy

  摘要：

  Mononuclear phagocytes are efficient drug delivery targets for cancers owing to their cancerous tissue-accumulating nature. As receptors of sialic acid, Siglecs (sialic acid-binding immunoglobulin-type lectins) are noticeably found on peripheral blood monocytes (PBMs) and tumor-associated macrophages (TAMs), which renew by the differentiation of recruited PBMs at the tumor site and positively correlate with tumor growth. Given this, a sialic acid-octadecylamine conjugate (SA-ODA) was synthesized and then modified on the surface of liposomal epirubicin (EPI-SAL) as a potent tumor-targeting delivery strategy. A cellular uptake assay indicated that SA-modified liposomes provided improved distribution of the drug in both PBMs and TAMs. Pharmacodynamic tests demonstrated that the antitumor efficacy of the EPI-SAL group was better than that of the other groups, owing to both inhibition of TAMs by EPI-SAL, and high-efficiency targeting of PBMs by EPI-SAL, after which PBMs containing EPI-SAL were recruited to the tumor site and then killed by EPI. Thus, an SA-based targeted delivery strategy effectively interdicted the generation of TAMs. Our research provides the feasibility of the SA-ODA decorated liposome as an active carrier for cancer immunotherapy.

  DOI：

  10.1016/j.ijpharm.2019.118706
• 作为产物：
  描述：

  3-nitrophenyl N-acetyl-α-D-neuraminidine 在 sodium hydroxide 、 水 、 sodium acetate 、 calcium chloride 、 magnesium chloride 作用下， 生成 间硝基苯酚 、 5-acetamido-3,5-dideoxy-D-glycero-D-galacto-2-nonulosonic acid
  参考文献：
  名称：

  Guo Xumin; Laver; Vimr, Journal of the American Chemical Society, 1994, vol. 116, # 13, p. 5572 - 5578

  摘要：

  DOI：

文献信息

• Preparation of oligosaccharides by homogenous enzymatic synthesis and solid phase extraction
  作者：Wenjun Wang、Chen Jin、Lina Guo、Yu Liu、Yue Wan、Xin Wang、Lei Li、Wei Zhao、Peng George Wang

  DOI：10.1039/c1cc13293h

  日期：——

  This communication describes a method for enzymatic preparation of bioactive glycans, which integrated the high-efficiency of homogenous phase enzymatic reaction and fast separation of solid phase extraction.

  该交流描述了一种酶法制备生物活性聚糖的方法，该方法集高效率的均相酶促反应和固相萃取的快速分离于一体。
• A Sensitive and Reversible Labeling Strategy Enables Global Mapping of the Core‐Fucosylated Glycoproteome on Cell Surfaces
  作者：Yinping Tian、Yuqiu Wang、Hongbo Yin、Yawen Luo、Fangyu Wei、Hu Zhou、Liuqing Wen

  DOI：10.1002/anie.202206802

  日期：2022.12.5

  Core-fucosylated glycoproteins that locate on cell surfaces can be selectively probed by a reversible labeling strategy, enabling the global mapping of the core-fucosylated glycoproteome.

  可以通过可逆标记策略选择性地探测位于细胞表面的核心岩藻糖基化糖蛋白，从而实现核心岩藻糖基化糖蛋白组的全局定位。
• Efficient Convergent Synthesis of Bi-, Tri-, and Tetra-antennary Complex Type <i>N</i>-Glycans and Their HIV-1 Antigenicity
  作者：Sachin S. Shivatare、Shih-Huang Chang、Tsung-I Tsai、Chien-Tai Ren、Hong-Yang Chuang、Li Hsu、Chih-Wei Lin、Shiou-Ting Li、Chung-Yi Wu、Chi-Huey Wong

  DOI：10.1021/ja409097c

  日期：2013.10.16

  The structural diversity of glycoproteins often comes from post-translational glycosylation with heterogeneous N-glycans. Understanding the complexity of glycans related to various biochemical processes demands a well-defined synthetic sugar library. We report herein a unified convergent strategy for the rapid production of bi-, tri-, and tetra-antennary complex type N-glycans with and without terminal N-acetylneuraminic acid residues connected via the alpha-2,6 or alpha-2,3 linkages. Moreover, using sialyltransferases to install sialic acid can minimize synthetic steps through the use of shared intermediates to simplify the complicated procedures associated with conventional sialic acid chemistry. Furthermore, these synthetic complex oligosaccharides were compiled to create a glycan array for the profiling of HIV-1 broadly neutralizing antibodies PG9 and PG16 that were isolated from HIV infected donors. From the study of antibody PG16, we identified potential natural and unnatural glycan ligands, which may facilitate the design of carbohydrate-based immunogens and hasten the HIV vaccine development.
• Inhibition of neuraminidase with neuraminic acid C -glycosides
  作者：Qun Wang、Michael Wolff、Tülay Polat、Yuguo Du、Robert J Linhardt

  DOI：10.1016/s0960-894x(00)00132-3

  日期：2000.5

  Neuraminic (sialic) acid based alpha-C-glycosides have been synthesized and their inhibitory activity towards bacterial neuraminidase (sialidase) was examined. While some C-glycosides were found to be potent inhibitors (K-i 15-30 mu M) of this neuraminidase, others afforded no measurable activity. The structure-activity relationship of these C-glycosides is discussed in the context of other previously reported sialidase inhibitors. (C) 2000 Elsevier Science Ltd. All rights reserved.