N-difluoroacetyl-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-difluoroacetyl-D-neuraminic acid
• 英文别名: (2S,4S,5R,6R)-5-[(2,2-difluoroacetyl)amino]-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• 化学式: C₁₁H₁₇F₂NO₉
• 分子量: 345.254
• InChiKey: RCHZBVQCKDNPMN-CIBNABSHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 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：
  177
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 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-difluoroacetyl-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

• INHIBITORS OF POLYSIALIC ACID DE-N-ACETYLASE AND METHODS FOR USING THE SAME
  申请人：Children's Hospital & Research Center at Oakland

  公开号：EP2173166A1

  公开（公告）日：2010-04-14
• US8999954B2
  申请人：——

  公开号：US8999954B2

  公开（公告）日：2015-04-07
• [EN] INHIBITORS OF POLYSIALIC ACID DE-N-ACETYLASE AND METHODS FOR USING THE SAME<br/>[FR] INHIBITEURS DE L'ACIDE POLYSIALIQUE DE-N-ACÉTYLASE ET PROCÉDÉS POUR LEUR UTILISATION
  申请人：CHILDRENS HOSP & RES CT OAK

  公开号：WO2009006591A1

  公开（公告）日：2009-01-08

  The invention relates to inhibitors of polysialic (PSA) de-N-acetylase, methods of their production and use. The methods involve use of a PSA de-N-acetylase inhibitor for modifying the growth of cells, such as inhibiting the growth of cancer cells. The compositions include an inhibitor of a PSA de-N-acetylase, such as N-substituted derivatives of the amino sugars hexosamine and neuraminic acid, as well as conjugates and aggregates. Also provided are pharmaceutical compositions that include a PSA de-N-acetylase inhibitor of the invention. Kits containing one or more inhibitor compositions of the invention, as well as methods of preparing the compositions also are provided.
• 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.