N-benzoyl-D-neuraminic acid | 13185-87-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-benzoyl-D-neuraminic acid
• 英文别名: N-benzoyl-β-D-neuraminic acid；N-Benzoyl-neuraminsaeure；(2S,4S,5R,6R)-5-benzamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• CAS: 13185-87-0
• 化学式: C₁₆H₂₁NO₉
• 分子量: 371.344
• InChiKey: JDKDBDDELDLBHE-OTUMZKFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  177
• 氢给体数：
  7
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2-苯甲酰胺基-2-脱氧-D-吡喃葡萄糖 在 sodium hydroxide 、 phosphate buffer 、 immobilised sialic acid aldolase 作用下， 以 水 为溶剂， 反应 236.0h， 生成 N-benzoyl-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

• Sialic Acid Derivatives Inhibit SiaT Transporters and Delay Bacterial Growth
  作者：Tiago Bozzola、Mariafrancesca Scalise、Christer U. Larsson、Michael C. Newton-Vesty、Caterina Rovegno、Ankita Mitra、Jonathan Cramer、Weixiao Yuan Wahlgren、Partha Radhakrishnan Santhakumari、Richard E. Johnsson、Oliver Schwardt、Beat Ernst、Rosmarie Friemann、Renwick C. J. Dobson、Cesare Indiveri、Jenny Schelin、Ulf J. Nilsson、Ulf Ellervik

  DOI：10.1021/acschembio.2c00321

  日期：2022.7.15

  are urgently needed. Here, we report the structure-based drug design, synthesis, and evaluation in vitro and in cellular systems of sialic acid derivatives able to inhibit the bacterial sialic acid symporter SiaT. We designed and synthesized 21 sialic acid derivatives and screened their affinity for SiaT by a thermal shift assay and elucidated the inhibitory mechanism through binding thermodynamics

  抗生素耐药性是全球关注的主要问题，迫切需要具有机制新颖作用模式的新药。在这里，我们报告了能够抑制细菌唾液酸转运体 SiaT 的唾液酸衍生物在体外和细胞系统中的基于结构的药物设计、合成和评价。我们设计并合成了 21 种唾液酸衍生物，并通过热位移分析筛选了它们对 SiaT 的亲和力，并通过结合热力学、计算方法和抑制动力学研究阐明了抑制机制。与天然底物相比，最有效的化合物具有 180 倍的亲和力，在细菌生长试验中进行了测试，表明耐甲氧西林金黄色葡萄球菌的细菌生长延迟. 这项研究代表了开发唾液酸摄取抑制剂作为新型抗菌剂的第一个例子和有希望的领先优势。
• Biological Properties of N-Acyl and N-Haloacetyl Neuraminic Acids: Processing by Enzymes of Sialic Acid Metabolism, and Interaction with Influenza Virus
  作者：A Humphrey

  DOI：10.1016/s0968-0896(02)00213-4

  日期：2002.10

  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.