5-acetamido-3,4,5-trideoxy-D-glycero-D-galacto-2-nonulosonic acid | 130264-75-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-acetamido-3,4,5-trideoxy-D-glycero-D-galacto-2-nonulosonic acid
• 英文别名: 5-acetamido-3,4,5-trideoxy-4-C-methyl-D-glycero-D-galacto-2-nonulonic acid；(2S,4S,5R,6R)-5-acetamido-2-hydroxy-4-methyl-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• CAS: 130264-75-4
• 化学式: C₁₂H₂₁NO₈
• 分子量: 307.301
• InChiKey: NMMRNRVLNUMDKU-HLQGBQNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  157
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  methyl (methyl 5-acetamido-3,4,5-trideoxy-4-C-methyl-8,9-O(methylethylidene)-β-D-glycero-D-galacto-2-nonulopyranosid)onate 在 盐酸 、 sodium hydroxide 、 Amberlyst 15H⁺ 作用下， 生成 5-acetamido-3,4,5-trideoxy-D-glycero-D-galacto-2-nonulosonic acid
  参考文献：
  名称：

  Structural variations of N-acetylneuraminic acid, part 19: Synthesis of both epimeric pairs of the 4-C-methyl- and 4-deoxy-4-C-methyl- as well as of the ?-methylketoside of 4-deoxy-4-C-methylene-N-acetylneuraminic acid

  摘要：

  While the reaction of the 4-oxo-Neu 5 Ac derivative 2a with tributoxy methyl zirconate led exclusively to equatorial 4-C-methyl derivative 3a, the analogous reaction with tetramethyl zirconate yielded a 3:2 mixture of both diastereoisomers 3a and 4a. After removal of protecting groups the 5-acetamido-3,4-dideoxy-4-C-methyl-D-glycero-D-galacto-2-nonulosoic acid 5a and 5-acetamido-3,4-dideoxy-4-C-methyl-D-glycero-D-talo-2-nonulosonic acid 6 a were obtained. The 4-C-methylene derivative was prepared by treatment of the same 4-oxo-derivative with CH2I2/Zn/Cp2ZrCl2. Subsequent hydrogenation led to both epimeric 4-deoxy-4-C-methyl derivatives 8a and 9a. Final removal of protecting groups gave the 5-acetamido-3,4,5-trideoxy-4-C-methyl-D-glycero-D-galacto-2-nonulosonic acid 10a respectively the 5-acetamido-2,7-anhydro-4-C-methyl-3,4,5-trideoxy-D-glycero-D-talo-2-nonulosonic acid 11a. The beta-methylketosides of the 4-deoxy-4-C-methyl- (16) and 4-C-methylene-Neu 5 Ac (15) were prepared via the peracetylated derivatives to obtain modell substrates for enzymatic studies. Thus all free acids were tested for inhibition of CMP-sialate synthase. Only the 4-C-methylene compound 15 showed most unexpectedly a strong competitive inhibition of this enzyme.

  DOI：

  10.1007/bf00815172

文献信息

• Synthesis of the epimeric pair of 4-deoxy-4-(R)- and 4-deoxy-4-(S)-C-methyl-n-acetylneuraminic acid
  作者：Michael Hartmann、Erich Zbiral

  DOI：10.1016/0040-4039(90)80171-h

  日期：1990.1
• HARTMANN, MICHAEL;ZBIRAL, ERICH, TETRAHEDRON LETT., 31,(1990) N0, C. 2875-2878
  作者：HARTMANN, MICHAEL、ZBIRAL, ERICH

  DOI：——

  日期：——
• Structural variations of N-acetylneuraminic acid, part 19: Synthesis of both epimeric pairs of the 4-C-methyl- and 4-deoxy-4-C-methyl- as well as of the ?-methylketoside of 4-deoxy-4-C-methylene-N-acetylneuraminic acid
  作者：Michael Hartmann、Rudolf Christian、Erich Zbiral

  DOI：10.1007/bf00815172

  日期：——

  While the reaction of the 4-oxo-Neu 5 Ac derivative 2a with tributoxy methyl zirconate led exclusively to equatorial 4-C-methyl derivative 3a, the analogous reaction with tetramethyl zirconate yielded a 3:2 mixture of both diastereoisomers 3a and 4a. After removal of protecting groups the 5-acetamido-3,4-dideoxy-4-C-methyl-D-glycero-D-galacto-2-nonulosoic acid 5a and 5-acetamido-3,4-dideoxy-4-C-methyl-D-glycero-D-talo-2-nonulosonic acid 6 a were obtained. The 4-C-methylene derivative was prepared by treatment of the same 4-oxo-derivative with CH2I2/Zn/Cp2ZrCl2. Subsequent hydrogenation led to both epimeric 4-deoxy-4-C-methyl derivatives 8a and 9a. Final removal of protecting groups gave the 5-acetamido-3,4,5-trideoxy-4-C-methyl-D-glycero-D-galacto-2-nonulosonic acid 10a respectively the 5-acetamido-2,7-anhydro-4-C-methyl-3,4,5-trideoxy-D-glycero-D-talo-2-nonulosonic acid 11a. The beta-methylketosides of the 4-deoxy-4-C-methyl- (16) and 4-C-methylene-Neu 5 Ac (15) were prepared via the peracetylated derivatives to obtain modell substrates for enzymatic studies. Thus all free acids were tested for inhibition of CMP-sialate synthase. Only the 4-C-methylene compound 15 showed most unexpectedly a strong competitive inhibition of this enzyme.