4-methylumbelliferyl 2-acetamido-2-deoxy-3-O-(4-deoxy-β-D-glucopyranosyluronic acid)-β-D-glucopyranoside | 1319805-99-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 4-methylumbelliferyl 2-acetamido-2-deoxy-3-O-(4-deoxy-β-D-glucopyranosyluronic acid)-β-D-glucopyranoside
• 英文别名: (2S,4S,5R,6R)-6-[(2R,3S,4R,5R,6S)-5-acetamido-3-hydroxy-2-(hydroxymethyl)-6-(4-methyl-2-oxochromen-7-yl)oxyoxan-4-yl]oxy-4,5-dihydroxyoxane-2-carboxylic acid
• CAS: 1319805-99-6
• 化学式: C₂₄H₂₉NO₁₃
• 分子量: 539.493
• InChiKey: JJWGRHFJNCIOTA-FQODWOQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  38
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  211
• 氢给体数：
  6
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  4-甲基香豆素-2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖苷 在 二苯基亚砜 、 sodium methylate 、 sodium carbonate 、 triethylamine tris(hydrogen fluoride) 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.25h， 生成 4-methylumbelliferyl 2-acetamido-2-deoxy-3-O-(4-deoxy-β-D-glucopyranosyluronic acid)-β-D-glucopyranoside
  参考文献：
  名称：

  A practical synthesis of capped 4-methylumbelliferyl hyaluronan disaccharides and tetrasaccharides as potential hyaluronidase substrates

  摘要：

  The synthesis of hyaluronan dimers and tetramers equipped with a 4-methylumbelliferyl group at the reducing end to potentially allow monitoring of hyaluronidase activities is described. The 4-OH at the non-reducing glucuronate in the presented series is either removed or methylated to prohibit transglycosylase reactions, leading to a total of four probes. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.03.042

文献信息

• A practical synthesis of capped 4-methylumbelliferyl hyaluronan disaccharides and tetrasaccharides as potential hyaluronidase substrates
  作者：Henrik Gold、Stefan Munneke、Jasper Dinkelaar、Herman S. Overkleeft、Johannes M.F.G. Aerts、Jeroen D.C. Codée、Gijs A. van der Marel

  DOI：10.1016/j.carres.2011.03.042

  日期：2011.9

  The synthesis of hyaluronan dimers and tetramers equipped with a 4-methylumbelliferyl group at the reducing end to potentially allow monitoring of hyaluronidase activities is described. The 4-OH at the non-reducing glucuronate in the presented series is either removed or methylated to prohibit transglycosylase reactions, leading to a total of four probes. (C) 2011 Elsevier Ltd. All rights reserved.