p-nitrophenyl 2-O-(β-D-glucopyranosyl)-β-D-glucopyranoside | 16790-33-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-nitrophenyl 2-O-(β-D-glucopyranosyl)-β-D-glucopyranoside
• 英文别名: p-Nitrophenyl sophoroside；(2S,3R,4S,5S,6R)-2-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(4-nitrophenoxy)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 16790-33-3
• 化学式: C₁₈H₂₅NO₁₃
• 分子量: 463.395
• InChiKey: ZGWCYKZKLZNQQX-GSPJEIBNSA-N

物化性质

• 熔点：
  245-250°C
• 沸点：
  795.6±60.0 °C(Predicted)
• 密度：
  1.70±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于水

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  224
• 氢给体数：
  7
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  L-丝氨酸 、 4-硝基苯-Β-D-吡喃葡萄糖苷 以 乙腈 为溶剂， 反应 0.17h， 以19%的产率得到p-nitrophenyl 2-O-(β-D-glucopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Galactosylation and glucosylation by use of β-galactosidase

  摘要：

  The transglycosylation activity of beta-galactosidase derived from Aspergillus oryzae and Escherichia coli, respectively, was examined in reaction systems containing up to 50% acetonitrile. Starting with ortho-nitrophenyl beta-galactoside (1), which functions both as donor and as acceptor, beta-Gal(1-6)beta-Gal-PhNO2-omicron (2) and beta-Gal(1-3)beta-Gal-PhNO2-omicron (3) were obtained. Under similar conditions the enzyme from A. oryzae converts para-nitrophenyl beta-glucoside (5) to beta-Glc(1-2)beta-Glc-PhNO2-p (6) and alpha-Glc(1-4)beta-Glc-PhNO2-p (7). Incubation of 1 and L-serine in the presence of the A. oryzae beta-galactosidase leads to beta-Gal-L-Ser (4).

  DOI：

  10.1016/0040-4039(92)88050-f

文献信息

• Galactosylation and glucosylation by use of β-galactosidase
  作者：Bernd Sauerbrei、Joachim Thiem

  DOI：10.1016/0040-4039(92)88050-f

  日期：1992.1

  The transglycosylation activity of beta-galactosidase derived from Aspergillus oryzae and Escherichia coli, respectively, was examined in reaction systems containing up to 50% acetonitrile. Starting with ortho-nitrophenyl beta-galactoside (1), which functions both as donor and as acceptor, beta-Gal(1-6)beta-Gal-PhNO2-omicron (2) and beta-Gal(1-3)beta-Gal-PhNO2-omicron (3) were obtained. Under similar conditions the enzyme from A. oryzae converts para-nitrophenyl beta-glucoside (5) to beta-Glc(1-2)beta-Glc-PhNO2-p (6) and alpha-Glc(1-4)beta-Glc-PhNO2-p (7). Incubation of 1 and L-serine in the presence of the A. oryzae beta-galactosidase leads to beta-Gal-L-Ser (4).