(4S,5R)-5-((1S,2R)-2-Azido-1-hydroxy-propyl)-2,2-dimethyl-[1,3]dioxolane-4-carbonitrile | 214897-78-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S,5R)-5-((1S,2R)-2-Azido-1-hydroxy-propyl)-2,2-dimethyl-[1,3]dioxolane-4-carbonitrile
• CAS: 214897-78-6
• 化学式: C₉H₁₄N₄O₃
• 分子量: 226.235
• InChiKey: AFXFUXBQQHSNCU-KVPKETBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.09
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  111.24
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (4S,5R)-5-((1S,2R)-2-Azido-1-hydroxy-propyl)-2,2-dimethyl-[1,3]dioxolane-4-carbonitrile 在 palladium on activated charcoal 氢气 、 三氟乙酸 作用下， 以 甲醇 、 氘代甲苯 为溶剂， 反应 45.0h， 生成 (3R,4R,5S,6R)-3,4,5-Trihydroxy-6-methyl-piperidin-2-one
  参考文献：
  名称：

  5-epi-Deoxyrhamnojirimycin is a potent inhibitor of an α-l-rhamnosidase: 5-epi-deoxymannojirimycin is not a potent inhibitor of an α-d-mannosidase

  摘要：

  Whereas deoxyrhamnojirimycin (LRJ) 1 shows no significant inhibition of naringinase (an alpha-L-rhamnosidase), its C-5 epimer 2 is a potent and specific inhibitor of the enzyme and demonstrates the value of unambiguous chemical synthesis of such materials in the evaluation of their biological properties. In contrast, moderately weak inhibition towards an alpha-D-mannosidase is shown by both deoxymannojirimycin (DMJ) 5 and its C-5 epimer 6. Mimics of L-rhamnose which are recognised by enzymes that synthesise or process L-rhamnose may inhibit el ther the biosynthesis of the sugar or its incorporation into mycobacterial cell walls, providing new strategies for the treatment of diseases such as tuberculosis and leprosy. Molecular modelling studies provide a rationale for the surprisingly potent activity of the C-S epimer 2 compared with LRJ 1 and support a general hypothesis that potent piperidine glycosidase inhibitors mimic the H-4(3) conformation Of the relevant glycopyranosyl cation intermediate. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00317-6
• 作为产物：
  描述：

  (3aR,6S,6aR)-6-((R)-1-Azido-ethyl)-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-4-one 在 吡啶 、 三氟甲磺酸酐 、 氨 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 (4S,5R)-5-((1S,2R)-2-Azido-1-hydroxy-propyl)-2,2-dimethyl-[1,3]dioxolane-4-carbonitrile
  参考文献：
  名称：

  5-epi-Deoxyrhamnojirimycin is a potent inhibitor of an α-l-rhamnosidase: 5-epi-deoxymannojirimycin is not a potent inhibitor of an α-d-mannosidase

  摘要：

  Whereas deoxyrhamnojirimycin (LRJ) 1 shows no significant inhibition of naringinase (an alpha-L-rhamnosidase), its C-5 epimer 2 is a potent and specific inhibitor of the enzyme and demonstrates the value of unambiguous chemical synthesis of such materials in the evaluation of their biological properties. In contrast, moderately weak inhibition towards an alpha-D-mannosidase is shown by both deoxymannojirimycin (DMJ) 5 and its C-5 epimer 6. Mimics of L-rhamnose which are recognised by enzymes that synthesise or process L-rhamnose may inhibit el ther the biosynthesis of the sugar or its incorporation into mycobacterial cell walls, providing new strategies for the treatment of diseases such as tuberculosis and leprosy. Molecular modelling studies provide a rationale for the surprisingly potent activity of the C-S epimer 2 compared with LRJ 1 and support a general hypothesis that potent piperidine glycosidase inhibitors mimic the H-4(3) conformation Of the relevant glycopyranosyl cation intermediate. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00317-6

文献信息

• Inhibition of naringinase (L-rhamnosidase) by piperidine analogues of L-rhamnose: Scaffolds for libraries incorporating trihydroxypipecolic acids
  作者：John P. Shilvock、Joseph R. Wheatley、Benjamin Davis、Robert J. Nash、Rhodri C. Griffiths、M.George Jones、Matthias Müller、Sarah Crook、David J. Watkin、Colin Smith、Gurdyal S. Besra、Patrick J. Brennan、George W.J. Fleet

  DOI：10.1016/0040-4039(96)01958-2

  日期：1996.11

  L-Deoxyrhamnojirimycin 1 does not inhibit naringinase significantly but 5-epi-L-deoxyrhamnojirimycin 2 is a potent inhibitor. Conversely, α-C-glycosides of 1 are good inhibitors of L-rhamnosidase whereas those of 2 are not. Intermediate azabicyclic lactones are likely to be of use for the incorporation of a number of trihydroxypipecolic acids into peptide libraries.

  L-Deoxyrhamnojirimycin 1不能显着抑制柚皮苷酶，但是5- epi -L-deoxyrhamnojirimycin 2是有效的抑制剂。相反，α-C-糖苷1是L-鼠李糖苷酶的良好抑制剂，而这些的2则不是。中间的氮杂双环内酯可能用于将许多三羟基哌酸掺入肽文库中。