3-deoxy-L-glycero-L-galacto-nonulosonic acid | 136342-81-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-deoxy-L-glycero-L-galacto-nonulosonic acid
• 英文别名: L-KDN；(2R,4R,5S,6S)-2,4,5-trihydroxy-6-[(1S,2S)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• CAS: 136342-81-9
• 化学式: C₉H₁₆O₉
• 分子量: 268.221
• InChiKey: CLRLHXKNIYJWAW-LQYHQKDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  168
• 氢给体数：
  7
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  甲醇 、 乙酸酐 、 3-deoxy-L-glycero-L-galacto-nonulosonic acid 在 AF 50W-X₈ resin (H⁺ form) 、 吡啶 、 4-二甲氨基吡啶 作用下， 反应 34.0h， 以4.6 mg的产率得到methyl 2,4,5,7,8,9-hexa-O-acetyl-3-deoxy-β-L-glycero-L-galacto-nonulosonate
  参考文献：
  名称：

  唾液酸（-）-KDN和某些差向异构体由（-）-3-脱氢-3-草酸或（-）-奎尼酸的合成。

  摘要：

  （-）-3-脱氢shi草酸（3-DHS，4）是现在可以从玉米糖浆中大量获得的C（7）砌块，也已经转化为唾液酸（-）-KDN（3）作为其C-7和C-8发射器。（-）-亚硫酸可以用于相同的目的。[结构：见文字]

  DOI：

  10.1021/ol049048y
• 作为产物：
  描述：

  在 四氧化锇 、 N-甲基吲哚酮 、 三氟乙酸 作用下， 以 水 、 丙酮 、 叔丁醇 为溶剂， 反应 122.0h， 生成 3-deoxy-L-glycero-L-galacto-nonulosonic acid
  参考文献：
  名称：

  唾液酸（-）-KDN和某些差向异构体由（-）-3-脱氢-3-草酸或（-）-奎尼酸的合成。

  摘要：

  （-）-3-脱氢shi草酸（3-DHS，4）是现在可以从玉米糖浆中大量获得的C（7）砌块，也已经转化为唾液酸（-）-KDN（3）作为其C-7和C-8发射器。（-）-亚硫酸可以用于相同的目的。[结构：见文字]

  DOI：

  10.1021/ol049048y

文献信息

• Unusual stereoselectivity in sialic acid aldolase-catalyzed aldol condensations: synthesis of both enantiomers of high-carbon monosaccharides
  作者：Chun Hung Lin、Takeshi Sugai、Randall L. Halcomb、Yoshitaka Ichikawa、Chi Huey Wong

  DOI：10.1021/ja00052a008

  日期：1992.12

  An inversion of stereoselectivity in aldol condensations catalyzed by sialic acid aldolase (from Escherichia coli, Shinko American Inc.) was observed when L-mannose, 6-deoxy-L-mannose, L-talose, 2-deoxy-L-glucose, 2-deoxy-L-rhamnose, N-acetyl-L-mannosamine, D-gulose, D-arabinose, and 2-azido-2-deoxy-L-mannose were used as acceptor substrates. In all substrates tested, except the last three, a complete inversion of stereoselectivity was observed; i.e., the C-nucleophile of pyruvate attacks the re face of the acceptor carbonyl instead of the si face as in the normal case for the enantiomeric substrates. Examination of the product distribution during the course of enzymatic reactions indicates that the stereoselectivity is thermodynamically controlled in nature; i.e., attack on the re face would take place if the resulting product would be more stable than the one from the si face attack. Both enantiomers of several high-carbon monosaccharides are now accessible via the aldolase reactions. A new practical procedure has also been developed for the preparation of the aldolase products where unreacted pyruvate (usually used in 7-fold excess to drive the reaction) is decomposed with pyruvate decarboxylase to simplify product isolation.
• Narvor, Christine Gautheron-Le; Ichikawa, Yoshitaka; Wong, Chi-Huey, Journal of the American Chemical Society, 1991, vol. 113, # 20, p. 7816 - 7818
  作者：Narvor, Christine Gautheron-Le、Ichikawa, Yoshitaka、Wong, Chi-Huey

  DOI：——

  日期：——
• Synthesis of the Sialic Acid (−)-KDN and Certain Epimers from (−)-3-Dehydroshikimic Acid or (−)-Quinic Acid
  作者：Martin G. Banwell、Natasha L. Hungerford、Katrina A. Jolliffe

  DOI：10.1021/ol049048y

  日期：2004.8.1

  (-)-3-Dehydroshikimic acid (3-DHS, 4), a C(7)-building block now available in large quantity from corn syrup, has been converted into the sialic acid (-)-KDN (3) as well as its C-7- and C-8-epimers. (-)-Quinic acid can be used for the same purpose. [structure: see text]

  （-）-3-脱氢shi草酸（3-DHS，4）是现在可以从玉米糖浆中大量获得的C（7）砌块，也已经转化为唾液酸（-）-KDN（3）作为其C-7和C-8发射器。（-）-亚硫酸可以用于相同的目的。[结构：见文字]