N-trifluoroacetyl-D-neuraminic acid

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-trifluoroacetyl-D-neuraminic acid
• 英文别名: Neu5TFA；TfaNH(-5d)b-Kdn；(2S,4S,5R,6R)-2,4-dihydroxy-5-[(2,2,2-trifluoroacetyl)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• 化学式: C₁₁H₁₆F₃NO₉
• 分子量: 363.245
• InChiKey: KDUKFELIEQWQND-GWGXJPQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  24
• 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：
  12

反应信息

• 作为反应物：
  描述：

  N-trifluoroacetyl-D-neuraminic acid 在 无机焦磷酸酶 、 1,4-dithio-D,L-threitol 、 CMP-sialic acid synthetase NSY-05 、 sodium methylate 、 三羟甲基氨基甲烷 、 magnesium chloride 、 manganese(ll) chloride 、 cytidine 5'-triphosphate disodium salt 作用下， 以 甲醇 、 水 为溶剂， 反应 53.0h， 生成 Neuα(2,3)Galβ(1,4)GlcαF
  参考文献：
  名称：

  化学工程的合成神经进化海星神经节苷脂LLG-3的化学合成。

  摘要：

  LLG-3寡糖-氟化物（参见方案）可以通过化学酶组装，并可以通过工程改造的糖内酰胺酶糖合酶与各种鞘氨醇轻松偶联。所述溶血 神经节苷脂产物酰化，以产生在异构天然分离物识别的单独的异构体，以及修饰的鞘糖脂。

  DOI：

  10.1002/anie.201204578
• 作为产物：
  描述：

  D-mannosamine 在 phosphate buffer 、 immobilised sialic acid aldolase 作用下， 以 甲醇 、 水 为溶剂， 反应 156.0h， 生成 N-trifluoroacetyl-D-neuraminic acid
  参考文献：
  名称：

  Biological Properties of N-Acyl and N-Haloacetyl Neuraminic Acids: Processing by Enzymes of Sialic Acid Metabolism, and Interaction with Influenza Virus

  摘要：

  Several unnatural N-acyl neuraminic acids (N-propionyl, N-hexanoyl, N-benzoyl, N-trifluoroacetyl, N-chloroacetyl, N-difluoroacetyl) were prepared enzymatically using immobilised sialic acid aldolase. N-Trifluoroacetyl- N-chloroacetyl- and N-difluoroacetyl neuraminic acids were shown to enhance up to 10-fold the rate of association of influenza virus A to a sialoglycolipid neomembrane by surface plasmon resonance, and were found to act as weak inhibitors (K-iapp 0.45-2.0 mM) of influenza virus neuraminidase. The N-propionyl, N-chloroacetyl- and N-difluoroacetyl neuraminic acids were found to be substrates for recombinant Escherichia coli CMP sialate synthase, to give the corresponding CMP-N-acyl-neuraminic acids. CMP-N-propionyl neuraminic acid was found not to be a substrate for CMP-N-acetyl neuraminic acid hydroxylase from pig submandibular gland. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00213-4

文献信息

• [EN] DERIVATIVES AND ANALOGUES OF 2-DEOXY-2,3-DIDEHYDRO-N-ACETYL NEURAMINIC ACID AND THEIR USE AS ANTIVIRAL AGENTS
  申请人：BIOTA SCIENTIFIC MANAGEMENT PTY LTD

  公开号：WO1991016320A1

  公开（公告）日：1991-10-31

  (EN) Derivatives and analogues of 2-deoxy-2,3-didehydro-N-acetyl neuraminic acid, pharmaceutical formulations thereof, methods for their preparation and their use in the treatment of viral infections, in particular influenza, are described.(FR) On décrit des dérivés et analogues d'acide 2-déoxy-2,3-didéhydro-N-acétyle neuraminique et leur utilisation comme agents antiviraux, leurs formulations pharmaceutiques, procédés de préparation et leur utilisation pour le traitement d'infections virales, en particulier de la grippe.

  （ZH）本文描述了2-脱氧-2,3-二脱氢-N-乙酰神经酰胺酸的衍生物和类似物，其制药配方，制备方法以及它们在治疗病毒感染，特别是流感方面的应用。
• Inhibition of tumor cell metastasis potential and invasiveness by chemically-defined oligosaccharides, their derivatives, mimetics and antibodies directed to them
  申请人：The Biomembrane Institute

  公开号：EP0521692A2

  公开（公告）日：1993-01-07

  Methods and compositions for inhibiting metastasis potential of tumor cells are provided. Metastasis potential of tumor cells may be inhibited by an agent selected from the group consisting of mimetics of monosialosyl-Lea I, monosialosyl-Lea II, disialosyl-Lea, and sialosyl Lex, the agent inhibiting the metastasis potential of the preparation. The present invention also discloses conjugates comprising the agent and poly(ethylene glycol). Methods for inhibiting GMP-140-mediated or ELAM-1-mediated cell aggregation or adhesion are also provided. The aggregation or adhesion at a tumor site can be inhibited by an agent selected from the group consisting of mimetics of monosialosyl-Lea I, monosialosyl-Lea II, disialosyl-Lea, and sialosyl Lex, the agent inhibiting the cell aggregation or adhesion.

  本研究提供了抑制肿瘤细胞转移潜能的方法和组合物。肿瘤细胞的转移潜能可由选自单唾液基-Lea I、单唾液基-Lea II、二唾液基-Lea 和 sialosyl Lex 的模拟物组成的组的制剂抑制，该制剂可抑制制剂的转移潜能。本发明还公开了由制剂和聚乙二醇组成的共轭物。本发明还提供了抑制 GMP-140 介导或 ELAM-1 介导的细胞聚集或粘附的方法。肿瘤部位的聚集或粘附可由选自单硅丙葡聚糖-Lea I、单硅丙葡聚糖-Lea II、二硅丙葡聚糖-Lea 和硅丙葡聚糖-Lex 的模拟物组成的组中的一种制剂抑制，该制剂可抑制细胞聚集或粘附。
• DERIVATIVES AND ANALOGUES OF 2-DEOXY-2,3-DIDEHYDRO-N-ACETYL NEURAMINIC ACID AND THEIR USE AS ANTIVIRAL AGENTS
  申请人：BIOTA SCIENTIFIC MANAGEMENT PTY. LTD.

  公开号：EP0526543A1

  公开（公告）日：1993-02-10
• EP0526543A4
  申请人：——

  公开号：EP0526543A4

  公开（公告）日：1993-04-21
• INHIBITION OF CELL ADHESION BY CHEMICALLY-DEFINED OLIGOSACCHARIDES, THEIR DERIVATIVES, MIMETICS, AND ANTIBODIES DIRECTED THERETO
  申请人：The Biomembrane Institute

  公开号：EP0638085A1

  公开（公告）日：1995-02-15