3-deoxy-D-glycero-D-galacto-2-nonulosonic acid | 145295-41-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-deoxy-D-glycero-D-galacto-2-nonulosonic acid
• 英文别名: 3-deoxy-D-glycero-L-altro-nonulosonic acid；(2S,4S,5R,6R)-2,4,5-trihydroxy-6-[(1S,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• CAS: 145295-41-6
• 化学式: C₉H₁₆O₉
• 分子量: 268.221
• InChiKey: CLRLHXKNIYJWAW-MRXKBSKTSA-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：

  3-deoxy-D-glycero-D-galacto-2-nonulosonic acid 在 吡啶 、 4-二甲氨基吡啶 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 methyl 2,4,5,7,8,9-hexa-O-acetyl-3-deoxy-D-glycero-β-D-galacto-2-nonulopyranosonate
  参考文献：
  名称：

  Studies on Sialic Acids. XXV. Synthesis of the .ALPHA.- and .BETA.-N-Glycosides of 3-Deoxy-D-glycero-D-galacto-2-nonulosonic Acid (KDN).

  摘要：

  在Vorbruggen和Williamson反应条件下合成了几种3-脱氧-D-甘油-D-半乳糖-2-非糖酸（1，KDN）的α-和β-N-糖苷。将两个六-O-乙酰基衍生物与嘧啶、5-氟嘧啶和5-甲基嘧啶的三甲基硅基衍生物及叠氮化三甲基硅烷反应，得到了1的α-和β-N-糖苷衍生物的混合物。将两个五-O-乙酰基-2-氯衍生物与2, 4(1H, 3H)-嘧啶二酮、5-氟-2, 4(1H, 3H)-嘧啶二酮和5-甲基-2, 4(1H, 3H)-嘧啶二酮的钠盐反应，只得到α-N-糖苷。这些化合物的异构体配置可以根据13C核磁共振谱分析中C-1的耦合模式进行阐明。

  DOI：

  10.1248/cpb.39.3140
• 作为产物：
  描述：

  α-D-(+)-塔罗糖 、 sodium pyruvate 在 potassium phosphate buffer 、 1,4-二巯基-2,3-丁二醇 作用下， 以 水 为溶剂， 反应 72.0h， 生成 3-deoxy-D-glycero-D-galacto-2-nonulosonic acid
  参考文献：
  名称：

  Unusual stereoselectivity in sialic acid aldolase-catalyzed aldol condensations: synthesis of both enantiomers of high-carbon monosaccharides

  摘要：

  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.

  DOI：

  10.1021/ja00052a008

文献信息

• Boric Acid Catalyzed Methyl Esterification of Sugar Acids
  作者：Stephan M. Levonis、Brighid B. Pappin、Alissa Sharp、Milton J. Kiefel、Todd A. Houston

  DOI：10.1071/ch13459

  日期：——

  Boric acid catalyzes methyl esterification of certain sugar acids (sialic acid, deaminated neuraminic acid) and related natural products (quinic acid) quite cleanly in some cases. However, closely related sugar acids (glucuronic acid, 3-deoxy-d-manno-oct-2-ulosonic acid) failed to esterify under the same conditions. Factors governing this dichotomy are discussed.

  硼酸在某些情况下非常干净地催化某些糖酸（唾液酸，脱氨基神经氨酸）和相关天然产物（奎宁酸）的甲基酯化。然而，密切相关的糖酸（葡糖醛酸，3-脱氧d -甘露-辛-2-糖酸）失败的相同的条件下酯化。讨论了控制这种二分法的因素。