N-propionyl-D-neuraminic acid benzyl glycoside | 15964-51-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-propionyl-D-neuraminic acid benzyl glycoside
• 英文别名: 2-Phenyl-prop5AC；(2R,4S,5R,6R)-4-hydroxy-2-phenylmethoxy-5-(propanoylamino)-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• CAS: 15964-51-9
• 化学式: C₁₉H₂₇NO₉
• 分子量: 413.425
• InChiKey: XDURJXFZCXMSHL-YZKZVDITSA-N

物化性质

• 沸点：
  778.8±60.0 °C(predicted)
• 密度：
  1.43±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  166
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N-propionyl-D-neuraminic acid benzyl glycoside 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以94%的产率得到N-propionyl-D-neuraminic acid
  参考文献：
  名称：

  Accessibility of N-acyl-d-mannosamines to N-acetyl-d-neuraminic acid aldolase

  摘要：

  N-Acetyl-D-neuraminic acid (NeuNAc) aldolase is an important enzyme for the metabolic engineering of cell-surface NeuNAc using chemically modified D-mannosamines. To explore the optimal substrates for this application, eight N-acyl derivatives Of D-mannosamine were prepared, and their accessibility to NcuNAc aldolase was quantitatively investigated. The N-propionyl-, N-butanoyl-, N-iso-butanoyl-, N-pivaloyl-, and N-phenylacetyl-D-mannosamines proved to be as good substrates as, or even better than, the natural N-acetyl-D-mannosamine, while the N-trifluoropropionyl and benzoyl derivatives were poor. It was proposed that the electronic effects might have a significant influence on the enzymatic aldol condensation reaction Of D-mannosamine derivatives, with electron-deficient acyl groups having a negative impact. The results suggest that N-propionyl-, N-butanoyl-, N-isobutanoyl-, and N-phenylacetyl-D-mannosamines may be employed to bioengineer NeuNAc on cells. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.05.028
• 作为产物：
  描述：

  methyl (benzyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosid)onate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 N-propionyl-D-neuraminic acid benzyl glycoside
  参考文献：
  名称：

  Accessibility of N-acyl-d-mannosamines to N-acetyl-d-neuraminic acid aldolase

  摘要：

  N-Acetyl-D-neuraminic acid (NeuNAc) aldolase is an important enzyme for the metabolic engineering of cell-surface NeuNAc using chemically modified D-mannosamines. To explore the optimal substrates for this application, eight N-acyl derivatives Of D-mannosamine were prepared, and their accessibility to NcuNAc aldolase was quantitatively investigated. The N-propionyl-, N-butanoyl-, N-iso-butanoyl-, N-pivaloyl-, and N-phenylacetyl-D-mannosamines proved to be as good substrates as, or even better than, the natural N-acetyl-D-mannosamine, while the N-trifluoropropionyl and benzoyl derivatives were poor. It was proposed that the electronic effects might have a significant influence on the enzymatic aldol condensation reaction Of D-mannosamine derivatives, with electron-deficient acyl groups having a negative impact. The results suggest that N-propionyl-, N-butanoyl-, N-isobutanoyl-, and N-phenylacetyl-D-mannosamines may be employed to bioengineer NeuNAc on cells. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.05.028

文献信息

• Accessibility of N-acyl-d-mannosamines to N-acetyl-d-neuraminic acid aldolase
  作者：Yanbin Pan、Tiffany Ayani、Janos Nadas、Shouming Wen、Zhongwu Guo

  DOI：10.1016/j.carres.2004.05.028

  日期：2004.8

  N-Acetyl-D-neuraminic acid (NeuNAc) aldolase is an important enzyme for the metabolic engineering of cell-surface NeuNAc using chemically modified D-mannosamines. To explore the optimal substrates for this application, eight N-acyl derivatives Of D-mannosamine were prepared, and their accessibility to NcuNAc aldolase was quantitatively investigated. The N-propionyl-, N-butanoyl-, N-iso-butanoyl-, N-pivaloyl-, and N-phenylacetyl-D-mannosamines proved to be as good substrates as, or even better than, the natural N-acetyl-D-mannosamine, while the N-trifluoropropionyl and benzoyl derivatives were poor. It was proposed that the electronic effects might have a significant influence on the enzymatic aldol condensation reaction Of D-mannosamine derivatives, with electron-deficient acyl groups having a negative impact. The results suggest that N-propionyl-, N-butanoyl-, N-isobutanoyl-, and N-phenylacetyl-D-mannosamines may be employed to bioengineer NeuNAc on cells. (C) 2004 Elsevier Ltd. All rights reserved.