4-methylumbelliferyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranoside | 80265-03-8

• 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-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R,6R)-5-acetamido-3,4-diacetyloxy-6-(4-methyl-2-oxochromen-7-yl)oxyoxan-2-yl]methyl acetate
• CAS: 80265-03-8
• 化学式: C₂₄H₂₇NO₁₁
• 分子量: 505.478
• InChiKey: UXRGMYFQEBYUQU-LBRNTXKHSA-N

物化性质

• 沸点：
  699.0±55.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  153
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  4-methylumbelliferyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 0.05h， 以75%的产率得到4-甲基伞形酮-2-乙酸胺基-2-脱氧-Α-D-吡喃葡糖苷
  参考文献：
  名称：

  4-Methylumbelliferyl 2-acetamido-2-deoxy-α-d-glucopyranoside, a fluorogenic substrate for N-acetyl-α-D-glucos-aminidase

  摘要：

  Condensation of dimeric 3,4,6-tri-O-acetyl-2-deoxy-2-nitroso-alpha-D-glucopyranosyl chloride with 4-methylumbelliferone gave crystalline 4-methylumbelliferyl 3,4,6-tri-O-acetyl-2-deoxy-2-oximino-alpha-D-arabino-hexopyranoside. Acetylation of this adduct, reduction of the resulting crude O-acetyloxime with borane in oxolane, and acetylation gave the 3,4,6-tri-O-acetyl derivative of 4-methylumbelliferyl 2-acetamido-2-deoxy-alpha-D-glucopyranoside (1). A new sensitive assay of N-acetyl-alpha-D-glucosaminidase (EC 3.2.1.50) is made possible by fluorometric measurement of 4-methylumbelliferone liberated by enzymic hydrolysis of glycoside 1. Such assays are illustrated by results obtained with enzyme preparations from pig liver and human-blood serum.

  DOI：

  10.1016/s0008-6215(00)84698-4
• 作为产物：
  描述：

  dimeric 3,4,6-tri-O-acetyl-2-deoxy-2-nitroso-α-D-glucopyranosyl chloride 在 吡啶 、 硼烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 192.08h， 生成 4-methylumbelliferyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  4-Methylumbelliferyl 2-acetamido-2-deoxy-α-d-glucopyranoside, a fluorogenic substrate for N-acetyl-α-D-glucos-aminidase

  摘要：

  Condensation of dimeric 3,4,6-tri-O-acetyl-2-deoxy-2-nitroso-alpha-D-glucopyranosyl chloride with 4-methylumbelliferone gave crystalline 4-methylumbelliferyl 3,4,6-tri-O-acetyl-2-deoxy-2-oximino-alpha-D-arabino-hexopyranoside. Acetylation of this adduct, reduction of the resulting crude O-acetyloxime with borane in oxolane, and acetylation gave the 3,4,6-tri-O-acetyl derivative of 4-methylumbelliferyl 2-acetamido-2-deoxy-alpha-D-glucopyranoside (1). A new sensitive assay of N-acetyl-alpha-D-glucosaminidase (EC 3.2.1.50) is made possible by fluorometric measurement of 4-methylumbelliferone liberated by enzymic hydrolysis of glycoside 1. Such assays are illustrated by results obtained with enzyme preparations from pig liver and human-blood serum.

  DOI：

  10.1016/s0008-6215(00)84698-4

文献信息

• SZWEDA, R.;SPOHR, U.;LEMIEUX, R. U.;SCHINDLER, D.;BISHOP, D. F.;DESNICK, +, CAN. J. CHEM., 67,(1989) N, C. 1388-1391
  作者：SZWEDA, R.、SPOHR, U.、LEMIEUX, R. U.、SCHINDLER, D.、BISHOP, D. F.、DESNICK, +

  DOI：——

  日期：——