4-nitrophenyl O-α-L-fucopyranosyl-(1->3)-2-acetamido-2-deoxy-β-D-glucopyranoside | 142329-80-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-nitrophenyl O-α-L-fucopyranosyl-(1->3)-2-acetamido-2-deoxy-β-D-glucopyranoside
• 英文别名: Fuc(a1-3)GlcNAc(b)-O-Ph(4-NO2)；N-[(2S,3R,4R,5S,6R)-5-hydroxy-6-(hydroxymethyl)-2-(4-nitrophenoxy)-4-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl]acetamide
• CAS: 142329-80-4
• 化学式: C₂₀H₂₈N₂O₁₂
• 分子量: 488.449
• InChiKey: HWVMCIPHVUPMRS-PIRDJKQGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  213
• 氢给体数：
  6
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  methyl 3,4-O-isopropylidene-1-thio-β-L-fucopyranoside 在 4 A molecular sieve 、 四丁基溴化铵 、 水 、 sodium hydride 、 三氟乙酸 、 copper(ll) bromide 作用下， 以 氯仿 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.5h， 生成 4-nitrophenyl O-α-L-fucopyranosyl-(1->3)-2-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  轻松合成硝基苯基寡糖，在其非还原端包含O-α-1-呋喃果糖-（1→3）-2-乙酰氨基-2-脱氧-β-d-吡喃葡萄糖基单元

  摘要：

  一种简便的合成4-硝基苯基O-α-L-呋喃核糖基-（1 ---- 3）-2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖苷，2-硝基苯基O-α- L-呋喃果糖基-（1 ---- 3）-O-（2-乙酰胺基-2-脱氧-β-D-葡萄糖基诺糖基）-（1 ---- 6）-2-乙酰胺基-2-脱氧- α-D-吡喃半乳糖苷，4-硝基苯基O-α-L-呋喃果糖基-（1 ---- 3）-O-（2-乙酰氨基-2-脱氧-β-D-葡萄糖基吡喃糖基）-（1-- --6）-α-D-甘露吡喃糖苷和4-硝基苯基O-α-L-呋喃果糖基-（1 ---- 3）-O-（2-乙酰氨基-2-脱氧-β-D-葡萄糖基吡喃糖基）-（1 ---- 6）-β-D-吡喃半乳糖苷是通过开发和使用3,4-O-异亚丙基-2-O-（4-甲氧基苄基）-1-硫代-β-甲基完成的L-岩藻糖苷为糖基供体。

  DOI：

  10.1016/s0008-6215(00)90562-7

文献信息

• β-Glycosyl Azides as Substrates for α-Glycosynthases: Preparation of Efficient α-L-Fucosynthases
  作者：Beatrice Cobucci-Ponzano、Fiorella Conte、Emiliano Bedini、Maria Michela Corsaro、Michelangelo Parrilli、Gerlind Sulzenbacher、Alexandra Lipski、Fabrizio Dal Piaz、Laura Lepore、Mosè Rossi、Marco Moracci

  DOI：10.1016/j.chembiol.2009.09.013

  日期：2009.10

  Fucose-containing oligosaccharides play a central role in physio-pathological events, and fucosylated oligosaccharides have interesting potential applications in biomedicine. No methods for the large-scale production of oligosaccharides are currently available, but the chemo-enzymatic approach is very promising. Glycosynthases, mutated glycosidases that synthesize oligosaccharides in high yields, have been demonstrated to be an interesting alternative. However, examples of glycosynthases available so far are restricted to a limited number of glycosidases families and to only one retaining alpha-glycosynthase. We show here that new mutants of two alpha-L-fucosidases are efficient alpha-L-fucosynthases. The approach shown utilized beta-L-fucopyranosyl azide as donor substrate leading to transglycosylation yields up to 91%. This is the first method exploiting a beta-glycosyl azide donor for alpha-glycosynthases; its applicability to the glycosynthetic methodology in a wider perspective is presented.
• Glycosidase‐Catalyzed Synthesis of Fucosyl Di‐ and Trisaccharide Derivatives Using α‐<scp>l</scp>‐Fucosidase from<i>Alcaligenes sp</i>
  作者：Xiaoxiong Zeng、Takeomi Murata、Taichi Usui

  DOI：10.1081/car-120023474

  日期：2003.1.8

  p-Nitrophenyl glycosides of di-and trisaccharides containing a (1-->2)-, (1-->3)-, (1-->4)-, or (1-->6)-linked alpha-L-fucosyl group were synthesized using the transglycosylation reaction mediated by alpha-L-fucosidase from Alcaligenes sp. with p-nitrophenyl glycosides of N-acetyllactosamine, lactose, D-GlcNAc, and D-Glc as acceptors. The enzymatic process for preparing these compounds is simple, and the yield is sufficiently high to make the method practical.
• A facile synthesis of nitrophenyl oligosaccharides containing the O-α-l-fucopyranosul-( 1 → 3)-2-acetamido-2-deoxy-β-d-glucopyranosyl unit at their nonreducing end
  作者：Rakesh K. Jain、Conrad F. Piskorz、Khushi L. Matta

  DOI：10.1016/s0008-6215(00)90562-7

  日期：1992.4

  A facile approach towards the synthesis of 4-nitrophenyl O-alpha-L-fucopyranosyl-(1----3)-2-acetamido-2-deoxy-beta-D-glucopyra nos ide, 2-nitrophenyl O-alpha-L-fucopyranosyl-(1----3)-O-(2-acetamido-2-deoxy-beta-D-glucop yra nosyl)- (1----6)-2-acetamido-2-deoxy-alpha-D-galactopyranoside, 4-nitrophenyl O-alpha-L-fucopyranosyl-(1----3)-O-(2-acetamido-2-deoxy-beta-D-glucop yra nosyl)- (1----6)-alpha-D-mannopyranoside

  一种简便的合成4-硝基苯基O-α-L-呋喃核糖基-（1 ---- 3）-2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖苷，2-硝基苯基O-α- L-呋喃果糖基-（1 ---- 3）-O-（2-乙酰胺基-2-脱氧-β-D-葡萄糖基诺糖基）-（1 ---- 6）-2-乙酰胺基-2-脱氧- α-D-吡喃半乳糖苷，4-硝基苯基O-α-L-呋喃果糖基-（1 ---- 3）-O-（2-乙酰氨基-2-脱氧-β-D-葡萄糖基吡喃糖基）-（1-- --6）-α-D-甘露吡喃糖苷和4-硝基苯基O-α-L-呋喃果糖基-（1 ---- 3）-O-（2-乙酰氨基-2-脱氧-β-D-葡萄糖基吡喃糖基）-（1 ---- 6）-β-D-吡喃半乳糖苷是通过开发和使用3,4-O-异亚丙基-2-O-（4-甲氧基苄基）-1-硫代-β-甲基完成的L-岩藻糖苷为糖基供体。