N-acetylneuraminic acid | 140850-42-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-acetylneuraminic acid
• 英文别名: sialic acid；(2R,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2S)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• CAS: 140850-42-6
• 化学式: C₁₁H₁₉NO₉
• 分子量: 309.273
• InChiKey: SQVRNKJHWKZAKO-MVSHAXDASA-N

物化性质

• 沸点：
  805.0±65.0 °C(Predicted)
• 密度：
  1?+-.0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.5
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  [Ir(pqa)₂(4-(N-(13-(3-boronobenzylamino)-4,7,10-trioxa-tridecanyl)aminocarbonyloxymethyl)-4’-methyl-2,2’-bipyridine)](PF₆)*HCl 、 N-acetylneuraminic acid 以 aq. phosphate buffer 、 二甲基亚砜 为溶剂， 生成
  参考文献：
  名称：

  环金属化铱（III）联吡啶-苯基硼酸络合物作为生物成像试剂和唾液酸的发光探针

  摘要：

  唾液酸在哺乳动物的发育，细胞间的附着和信号传导中起着重要的作用。由于癌细胞利用其过表达的唾液酸化抗原来传播转移，因此唾液酸探针的开发非常重要。在本文中，我们报告了三个带有苯基硼酸（PBA）部分的发光环金属化铱（III）联吡啶配合物。分光光度滴定表明，PBA配合物对最常见的唾液酸N表现出更高的结合亲和力-乙酰神经氨酸（Neu5Ac）与糖蛋白上常见的单糖相比。值得注意的是，细胞成像和吸收实验表明，PBA复合物能够识别细胞唾液酸残基，从而比无硼酸类似物吸收更有效。另外，显示出一种PBA复合物可区分癌细胞和非癌细胞。

  DOI：

  10.1002/asia.201700359

文献信息

• Strukturelle Abwandlungen an N-Acetylneuramins�ure, 25. Mitt.: Synthese von Methyl-2-?-glycosiden von 4-epi-, 7-epi-, 8-epi- und 7,8-bis-epi-N-Acetylneuramins�ure
  作者：B. P. Bandgar、E. Zbiral

  DOI：10.1007/bf00811116

  日期：1991.12

  The alpha-methylketoside of N-acetylneuraminic acid methylester (4) is transformed via the deacetylated compound 5 into the 9,8-O-isopropylidenderivative 6 which could be oxidized regioselectivity by RuO4 to the corresponding 4-oxo-sialic acid analogue 7. Reduction with the borane-ammonia complex produces a 1:1 mixture of 6 and the desired alpha-methylketoside of 9,8-O-isopropyliden-4-epi-N-acetyl-neuraminic acid methylester (8). Removing of the isopropylidene group gives the alpha-methylketoside of 4-epi-N-acetylneuraminic acid alpha-methylketoside (10). On the other hand compound 5 was turned into the 4,8,9-tri-O-t-butyldimethylsilylderivative 11 a from which the corresponding 7-oxo-compound 12 by oxidation with RuO4 derives. The reduction of 12 with BH3 - NH3 yielded a 1:1 mixture of the starting material 11 a and the desired 7-epi-derivative 13 a which gives either via the purified peracetylated alpha-methylketosid of 7-epi-N-acetylneuraminic acid methylester (14) or a direct saponification the sodium salt of 7-epi-N-acetylneuraminic acid-alpha-methylketoside (15).Applying the Konigs-Knorr procedure to the peracetylated 8-epi-N-acetylneuraminic acid methylester (16) gives rise to the formation of a 1:1 mixture of the corresponding alpha- and beta-methylketosides 17 and 18 besides traces of the corresponding 2,3-dideoxy-2,3-dideohydro-sialic acid derivative 19. After chromatographic separation of 17 further saponification leads to the sodium salt of 8-epi-N-acetylneuraminic acid-alpha-methylketoside (20). In an analogous procedure the sodium salt of 7,8-di-epi-N-acetylneuraminic acid-alpha-methylketoside (25) was prepared starting from the peracetylated 7,8-di-epi-N-acetylneuraminic acid methylester (21), whereby a mixture of the alpha- and beta-methylketosides 22 and 23 was formed in a ratio 95:5 besides traces of the peracetylated 2,3-dideoxy-2,3-didehydrosialic acid methylester (24).