N-propanoylneuraminic acid | 76123-52-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-propanoylneuraminic acid
• 英文别名: 3,5-Dideoxy-5-(Propanoylamino)-D-Glycero-Alpha-D-Galacto-Non-2-Ulopyranosonic Acid；(2R,4S,5R,6R)-2,4-dihydroxy-5-(propanoylamino)-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• CAS: 76123-52-9
• 化学式: C₁₂H₂₁NO₉
• 分子量: 323.3
• InChiKey: QZBCMZXFDLYCRV-BLMTXZDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  1,2-二氨基-4,5-亚甲基二氧基苯双盐酸盐 、 N-propanoylneuraminic acid 生成
  参考文献：
  名称：

  Fluorination of mammalian cell surfaces via the sialic acid biosynthetic pathway

  摘要：

  Metabolic oligosaccharide engineering has been employed to introduce fluorine-containing groups onto mammalian cell surfaces. Incubation of HeLa, Jurkat, and HL60 cells in culture with fluorinated sialic acid and mannosamine analogues resulted in cell-surface presentation of fluorinated glycans. Metabolic conversion of fluorinated precursors was detected and quantified by DMB-derivatization and HPLC ESI-MS analysis. Between 7% and 72% of total membrane-associated sialosides were fluorinated, depending on the precursor used and the cell type. Fluorination of mammalian cell surfaces provides a means for introducing a bioorthogonal surface for modulating noncovalent interactions such as those involved in cell adhesion. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.09.010
• 作为产物：
  描述：

  methyl (5-N-propionyl-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl)onate 在 sodium methylate 、 水 、 lithium hydroxide 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 3-[(2S,3S,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-(propanoylamino)oxan-2-yl]-2-oxopropanoic acid 、 N-propanoylneuraminic acid
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of N-Acyl Modified Sialic Acids as Inhibitors of Adenoviruses Causing Epidemic Keratoconjunctivitis

  摘要：

  The adenovirus serotype Ad37 binds to and infects human corneal epithelial (HCE) cells through attachment to cellular glycoproteins carrying terminal sialic acids. By use of the crystallographic structure of the sialic acid-interacting domain of the Ad37 fiber protein in complex with sialyllactose, a set of N-acyl modified sialic acids were designed to improve binding affinity through increased hydrophobic interactions. These N-acyl modified sialic acids and their corresponding multivalent human serum albumin (HSA) conjugates were synthesized and tested in Ad37 cell binding and cell infectivity assays. Compounds bearing small substituents were as effective inhibitors as sialic acid. X-ray crystallography and overlays with the Ad37-sialyllactose complex showed that the N-acyl modified sialic acids were positioned in the same orientation as sialic acid. Their multivalent counterparts achieved a strong multivalency effect and were more effective to prevent infection than the monomers. Unfortunately, they were less active as inhibitors than multivalent sialic acid.

  DOI：

  10.1021/jm801609s

文献信息

• Synthesis and NMR assignment of two repeating units (decasaccharide) of the type III group B Streptococcus capsular polysaccharide and its13 C-labeled and N-propionyl substituted sialic acid analogues
  作者：Z Wei

  DOI：10.1016/s0008-6215(96)00236-4

  日期：1996.12.13
• Fluorination of mammalian cell surfaces via the sialic acid biosynthetic pathway
  作者：Laila Dafik、Marc d’Alarcao、Krishna Kumar

  DOI：10.1016/j.bmcl.2008.09.010

  日期：2008.11

  Metabolic oligosaccharide engineering has been employed to introduce fluorine-containing groups onto mammalian cell surfaces. Incubation of HeLa, Jurkat, and HL60 cells in culture with fluorinated sialic acid and mannosamine analogues resulted in cell-surface presentation of fluorinated glycans. Metabolic conversion of fluorinated precursors was detected and quantified by DMB-derivatization and HPLC ESI-MS analysis. Between 7% and 72% of total membrane-associated sialosides were fluorinated, depending on the precursor used and the cell type. Fluorination of mammalian cell surfaces provides a means for introducing a bioorthogonal surface for modulating noncovalent interactions such as those involved in cell adhesion. (C) 2008 Elsevier Ltd. All rights reserved.
• Design, Synthesis, and Evaluation of <i>N</i>-Acyl Modified Sialic Acids as Inhibitors of Adenoviruses Causing Epidemic Keratoconjunctivitis
  作者：Susanne Johansson、Emma Nilsson、Weixing Qian、Delphine Guilligay、Thibaut Crepin、Stephen Cusack、Niklas Arnberg、Mikael Elofsson

  DOI：10.1021/jm801609s

  日期：2009.6.25

  The adenovirus serotype Ad37 binds to and infects human corneal epithelial (HCE) cells through attachment to cellular glycoproteins carrying terminal sialic acids. By use of the crystallographic structure of the sialic acid-interacting domain of the Ad37 fiber protein in complex with sialyllactose, a set of N-acyl modified sialic acids were designed to improve binding affinity through increased hydrophobic interactions. These N-acyl modified sialic acids and their corresponding multivalent human serum albumin (HSA) conjugates were synthesized and tested in Ad37 cell binding and cell infectivity assays. Compounds bearing small substituents were as effective inhibitors as sialic acid. X-ray crystallography and overlays with the Ad37-sialyllactose complex showed that the N-acyl modified sialic acids were positioned in the same orientation as sialic acid. Their multivalent counterparts achieved a strong multivalency effect and were more effective to prevent infection than the monomers. Unfortunately, they were less active as inhibitors than multivalent sialic acid.