(4S,5R,6R)-4-羟基-5-[(2-羟基乙酰基)氨基]-6-[(1R,2R)-1,2,3-三羟基丙基]-5,6-二氢-4H-吡喃-2-羧酸 | 39937-91-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: (4S,5R,6R)-4-羟基-5-[(2-羟基乙酰基)氨基]-6-[(1R,2R)-1,2,3-三羟基丙基]-5,6-二氢-4H-吡喃-2-羧酸
• 英文名称: 2,6-anhydro-3,5-dideoxy-5-(2-hydroxyacetamido)-D-glycero-D-galacto-non-2-enoic acid
• 英文别名: 2,6-anhydro-3,5-dideoxy-5-(2-hydroxyacetamido)-D-glycero-D-galacto-non-2-enonicacid；2,6-anhydro-3,5-dideoxy-5-glycolylamido-D-glycero-D-galacto-non-2-enonic acid；2-deoxy-N-glycoloyl-2,3-didehydroneuraminic acid；Neu5Gc2en；2-Deoxy-2,3-didehydro-N-glycoloylneuraminic acid；(2R,3R,4S)-4-hydroxy-3-[(2-hydroxyacetyl)amino]-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid
• CAS: 39937-91-2
• 化学式: C₁₁H₁₇NO₉
• 分子量: 307.257
• InChiKey: FDONZIZJWIPGCO-NCJYIMSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.2
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  177
• 氢给体数：
  7
• 氢受体数：
  9

安全信息

• 储存条件：
  存放在惰性气体中，并且避免与空气接触和加热。温度应保持在低于0°C。

反应信息

• 作为反应物：
  描述：

  1-乙酰基咪唑 、 (4S,5R,6R)-4-羟基-5-[(2-羟基乙酰基)氨基]-6-[(1R,2R)-1,2,3-三羟基丙基]-5,6-二氢-4H-吡喃-2-羧酸 以 吡啶 为溶剂， 反应 12.0h， 生成 9-O-acetyl-2-deoxy-N-glycoloyl-2,3-didehydroneuraminic acid 、 5-acetoxyacetamido-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enoinic acid
  参考文献：
  名称：

  O-酰化的2,3-不饱和唾液酸的天然存在和制备

  摘要：

  三种O-酰化的不饱和唾液酸，N-乙酰基-9-O-乙酰基-，N-乙酰基-9-O-乳酰基-和2-脱氧-N-乙醇酰基-9-O-乳酰基-2,3-双氢尿嘧啶酸（5-乙酰氨基-9-O-乙酰基-，5-乙酰氨基-9-O-乳酰基-和2,6-脱水-3,5-二甲氧基-5-糖基酰氨基-9-O-乳酰基-D-从大鼠，猪和牛的尿液或下颌下腺中分离得到甘油-Dg乳酸-非-2-烯酸。还获得了在猪尿液中存在2,3-不饱和9-O-乙酰基-N-糖酰神经氨酸的质谱证据。唾液酸通过透析，凝胶和离子交换色谱以及制备型薄层色谱进行纯化。通过薄层色谱法，高压液相色谱法和毛细管气相色谱法-质谱法对它们进行了分析。为了比较，合成了O-乙酰化的不饱和唾液酸。

  DOI：

  10.1016/0008-6215(87)80026-5
• 作为产物：
  描述：

  N-acetyl-D-mannosamine 在 CMP-唾液酸合成酶 、 Pasteurella multocida sialic acid aldolase 、 Pasteurella multocida sialyltransferase 1 mutant 、 potassium carbonate 、 胞苷-5’-三磷酸 、 sodium hydroxide 、 magnesium chloride 作用下， 以 甲醇 为溶剂， 反应 19.0h， 生成 (4S,5R,6R)-4-羟基-5-[(2-羟基乙酰基)氨基]-6-[(1R,2R)-1,2,3-三羟基丙基]-5,6-二氢-4H-吡喃-2-羧酸
  参考文献：
  名称：

  [EN] SIALIDASE INHIBITORS AND PREPARATION THEREOF
  [FR] INHIBITEURS DE SIALIDASE ET LEUR PRÉPARATION

  摘要：

  公开号：

  WO2018201058A3

文献信息

• Microwave-assisted synthesis of N-glycolylneuraminic acid derivatives
  作者：Pradeep Chopra、Paul D. Madge、Robin J. Thomson、I. Darren Grice、Mark von Itzstein

  DOI：10.1016/j.tetlet.2013.07.107

  日期：2013.10

  A rapid, efficient and scalable synthesis of biologically-relevant N-glycolylneuraminic acid derivatives from the natural N-acetyl (Neu5Ac) precursors has been developed. Microwave irradiation provides accelerated de-N-acetylation compared to more traditional methods, with optimised NaOH-promoted de-N-acetylation in only 15 min. The prepared amines were readily re-N-acylated to afford the corresponding N-glycolyl (Neu5Gc) analogues. (C) 2013 Elsevier Ltd. All rights reserved.
• The design, synthesis and biological evaluation of neuraminic acid-based probes of Vibrio cholerae sialidase
  作者：Jennifer C Wilson、Robin J Thomson、Jeffrey C Dyason、Pas Florio、Kaylene J Quelch、Samia Abo、Mark von Itzstein

  DOI：10.1016/s0957-4166(99)00552-2

  日期：2000.1

  A molecular modelling study using the program GRID has been used to investigate the structural requirements of a potential inhibitor binding to Vibrio cholerae sialidase. A number of favourable interactions were predicted between the sialidase and Neu2en derivatives containing hydroxyl- or halogen-substituted acyl groups on the C-5 amine. As a result of this study, a detailed analysis of the interactions of C-5-substituted Neu2en derivatives with the active site of V. cholerae sialidase was undertaken using a conformational searching routine based on molecular dynamics. Based on the results of these molecular design studies several N-acyl-Neu2en-based probes were prepared and evaluated for sialidase inhibition. As envisaged, and pleasingly, the designed compounds were found to be accommodated by the enzyme's active site architecture, and to be strong inhibitors of V. cholerae sialidase. (C) 2000 Elsevier Science Ltd. All rights reserved.