9-azido-9-deoxy-N-acetylneuraminic acid

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 9-azido-9-deoxy-N-acetylneuraminic acid
• 英文别名: (2S,4S,5R,6R)-5-acetamido-6-((1R,2R)-3-azido-1,2-dihydroxypropyl)-2,4-dihydroxytetrahydro-2H-pyran-2-carboxylic acid；9-azidosialic acid；9-azido-N-acetylneuraminic acid；(2S,4S,5R,6R)-5-acetamido-6-[(1R,2R)-3-azido-1,2-dihydroxypropyl]-2,4-dihydroxyoxane-2-carboxylic acid
• 化学式: C₁₁H₁₈N₄O₈
• 分子量: 334.286
• InChiKey: ZQEYNHOXMPPCHQ-PFQGKNLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  171
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  9-azido-9-deoxy-N-acetylneuraminic acid 在 Campylobacter jejuni α-2,3-sialyltransferase Cst-I 、 Neisseria meningitidis CMP-sialic acid synthethase NSY-05 、 sodium hydroxide 、 magnesium chloride 、 manganese(ll) chloride 、 alkaline phosphatase 作用下， 以 水 为溶剂， 生成 (5-acetamido-9-azido-3,5,9-trideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2→3)-β-D-galactopyranosyl-(1→4)-β-D-glucopyranosyl-(1→1)-(2S,3R,4E)-2-amino-4-octadecene-1,3-diol
  参考文献：
  名称：

  Glycosphingolipid synthesis employing a combination of recombinant glycosyltransferases and an endoglycoceramidase glycosynthase

  摘要：

  红球菌属的糖合酶突变体。内切糖神经酰胺酶 II 可有效合成复杂的鞘糖脂。糖基氟供体可以通过连续糖基转移酶催化的乳糖基氟糖基化来组装。或者，乳糖酰氟可以在随后的糖基化步骤之前与鞘氨醇偶联。

  DOI：

  10.1039/c1cc13885e
• 作为产物：
  描述：

  N-acetyl-D-mannosamine 在 吡啶 、 sodium azide 、 DL-dithiothreitol 、 三氟化硼乙醚 、 sodium methylate 、 sodium acetate 、 溶剂黄146 、 sodium iodide 、 palladium dichloride 作用下， 以 甲醇 、 硝基甲烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丁酮 为溶剂， 反应 63.58h， 生成 9-azido-9-deoxy-N-acetylneuraminic acid
  参考文献：
  名称：

  Overproduction of CMP-sialic acid synthetase for organic synthesis

  摘要：

  The gene coding for Escherichia coli CMP-sialic acid synthetase (E.C. 2.7.7.43) was cloned and overexpressed in E. coli through a primer-directed polymerase chain reaction. Two plasmids were constructed to produce the native enzyme and a modified enzyme fused with a decapeptide at the C-terminus. The decapeptide tag was used for detection of the enzyme production. Both enzymes produced from E. coli were isolated and purified with an Orange A dye resin and FPLC. Their properties were compared with respect to their kinetic parameters, stability, pH profiles, and substrate specificities. Both enzymes have similar k(cat) and K(m) for NeuAc and CTP but different pH profiles. Contrary to the native enzyme, the modified enzyme is more active at higher pH. Studies on specificity indicate that both enzymes have a high specific activity for C-9 modified NeuAc derivatives at neutral pH. Some C-5 modified (hydroxy, deoxy, and deoxyfluoro) NeuAc derivatives are not acceptable as substrates. The modified enzyme has been used in the synthesis of CMP-NeuAc from ManNAc and CMP and sialyl N-acetyllactosamine (Neu-alpha-2,6Gal-beta-1,4GlcNAc) with in situ generation of NeuAc and regeneration of CMP-NeuAc. The 6-O-acyl derivatives of ManNAc were prepared via transesterification in anhydrous dimethylformamide by using an engineered stable subtilisin variant as a catalyst, and the products were used as substrates in sialic acid aldolase-catalyzed synthesis of 9-O-acyl-NeuAc derivatives.

  DOI：

  10.1021/ja00036a044

文献信息

• Systemic Fluorescence Imaging of Zebrafish Glycans with Bioorthogonal Chemistry
  作者：Paresh Agarwal、Brendan J. Beahm、Peyton Shieh、Carolyn R. Bertozzi

  DOI：10.1002/anie.201504249

  日期：2015.9.21

  Vertebrate glycans constitute a large, important, and dynamic set of post‐translational modifications that are notoriously difficult to manipulate and image. Although the chemical reporter strategy has been used in conjunction with bioorthogonal chemistry to image the external glycosylation state of live zebrafish and detect tumor‐associated glycans in mice, the ability to image glycans systemically within

  脊椎动物聚糖构成了一组庞大、重要且动态的翻译后修饰，众所周知，它们很难操作和成像。尽管化学报告策略已与生物正交化学结合使用，对活体斑马鱼的外部糖基化状态进行成像并检测小鼠中的肿瘤相关聚糖，但对活体生物体内的聚糖进行系统成像的能力仍然难以捉摸。在这里，我们报告了一种将环辛炔功能化唾液酸衍生物的代谢掺入与荧光四嗪的连接反应相结合的方法，从而可以对活体斑马鱼胚胎内的唾液酸化糖缀合物进行成像。
• Development of BODIPY labelled sialic acids as sialyltransferase substrates for direct detection of terminal galactose on N- and O-linked glycans
  作者：Tasnim Abukar、Sadia Rahmani、Nicole K. Thompson、Costin N. Antonescu、Warren W. Wakarchuk

  DOI：10.1016/j.carres.2021.108249

  日期：2021.2

  N-acetylneuraminic acid (sialic acid) is a key player in these interactions and the manipulation and control of sialylation levels has been an important research focus, particularly in the development of therapeutic proteins. Using sialyltransferases to tag specific glycans provides a rapid means of determining what types of glycans are present. We have synthesized two variants of sialic acid carrying the

  蛋白质和细胞表面上的聚糖是有用的生物标记，可用于确定与聚糖结合蛋白的功能相互作用，潜在的疾病状态或实际上的分化水平。快速灵敏地检测或标记蛋白质上特定聚糖的能力提供了一种在化学糖生物学中广泛应用的诊断工具。单糖N-乙酰神经氨酸（唾液酸）是这些相互作用的关键参与者，唾液酸化水平的操纵和控制一直是重要的研究重点，尤其是在治疗性蛋白质的开发中。使用唾液酸转移酶标记特定的聚糖提供了一种确定存在何种类型的聚糖的快速方法。我们合成了带有荧光团BODIPY（4,4-Difluoro-4-boro-3a，4a-diaza-s-indacene），并研究了其与多种蛋白质底物和细胞表面聚糖上的几种不同的唾液酸转移酶的使用。我们的数据表明，各种酶转移标记的唾液酸的能力之间存在显着差异，并且N-聚糖和目标蛋白的类型强烈影响这种活性。
• Synthesis and biological evaluation of sialyl-oligonucleotide conjugates targeting leukocyte B trans-membranal receptor CD22 as delivery agents for nucleic acid drugs
  作者：Gabrielle St-Pierre、Sudip Pal、Michael E. Østergaard、Tianyuan Zhou、Jinghua Yu、Michael Tanowitz、Punit P. Seth、Stephen Hanessian

  DOI：10.1016/j.bmc.2016.03.047

  日期：2016.6

  Antisense oligonucleotides (ASOs) modified with ligands which target cell surface receptors have the potential to significantly improve potency in the target tissue. This has recently been demonstrated using triantennary N-acetyl D-galactosamine conjugated ASOs. CD22 is a cell surface receptor expressed exclusively on B cells thus presenting an attractive target for B cell specific delivery of drugs. Herein, we reported the synthesis of monovalent and trivalent ASO conjugates with biphenylcarbonyl (BPC) modified sialic acids and their study as ASO delivery agents into B cells. CD22 positive cells exhibited reduced potency when treated with ligand modified ASOs and mechanistic examination suggested reduced uptake into cells potentially as a result of sequestration of ASO by other cell-surface proteins. (C) 2016 Elsevier Ltd. All rights reserved.
• Redirection of CAR-T Cell Cytotoxicity Using Metabolic Glycan Labeling with Unnatural Sugars
  作者：Jeong Hyeon Cha、Eunsu Kim、Hyeong Ji Lee、Young-Ho Lee、Jeonghyun Lee、Eunha Kim、Chan Hyuk Kim

  DOI：10.1021/acs.jmedchem.3c00048

  日期：2023.6.22