rehmaglupentasaccharide C | 125419-02-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: rehmaglupentasaccharide C
• 英文别名: α-D-Galp-(1-6)-α-D-Galp-(1-6)-α-D-Glcp-(1-2)-β-D-Fruf-(1-2)-β-D-Fruf；1(F)-fructofuranosyl stachyose；α-D-Galp-(1->6)-α-D-Galp-(1->6)-α-D-Glcp-(1->2)-β-D-Fruf-(1->2)-β-D-Fruf；(2S,3R,4S,5R,6R)-2-[[(2R,3R,4S,5R,6S)-6-[[(2R,3S,4S,5R,6R)-6-[(2S,3S,4S,5R)-2-[[(2R,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-3,4,5-trihydroxyoxan-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 125419-02-5
• 化学式: C₃₀H₅₂O₂₆
• 分子量: 828.727
• InChiKey: FVJJKNOVAGVKCU-QGOLSBRXSA-N

物化性质

• 沸点：
  1198.9±65.0 °C(Predicted)
• 密度：
  1.86±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -9.8
• 重原子数：
  56
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  427
• 氢给体数：
  17
• 氢受体数：
  26

反应信息

• 作为反应物：
  描述：

  rehmaglupentasaccharide C 在 盐酸 、 水 作用下， 以1.87 mg的产率得到口服葡萄糖
  参考文献：
  名称：

  地黄根中的七种新五糖

  摘要：

   抽象的 从地黄的风干根中分离出七种新的五糖 ( 1 – 7 )，即红葡五糖 AG。它们的结构是根据获得的光谱数据和化学证据确定的。在当前的研究中还获得了已知的毛蕊花糖 ( 8 ) 和水苏糖 ( 9 )，并且使用 X 射线衍射数据明确地定义了水苏糖的结构。测试了化合物1 – 9对五种人类肿瘤细胞系的细胞毒性、对多巴胺受体激活的影响以及对罗伊氏乳杆菌的增殖作用。

  DOI：

  10.1080/10286020.2023.2184356
• 作为产物：
  描述：

  D-水苏糖 在 enzymatic preparation from Aspergillus aculeatus Pectinex Ultra SP-L 作用下， 反应 1.0h， 以21%的产率得到manninotriose
  参考文献：
  名称：

  Study of Influential Factors on Oligosaccharide Formation by Fructosyltransferase Activity during Stachyose Hydrolysis by Pectinex Ultra SP-L

  摘要：

  The influence of reaction conditions for oligosaccharide synthesis from stachyose using a commercial enzymatic preparation from Aspergillus aculeatus (Pectinex Ultra SP-L) was studied. Oligosaccharides were analyzed by gas chromatography with flame ionization detection (GC-FID) and matrix-assisted laser desorption/ionization-time-of-flight-mass spectrometry (MALDI-TOF-MS). Galactosyl-melibiose (DP3) was synthesized as a result of fructosidase activity, whereas fructosyl-stachyose (DP5) and difructosyl-stachyose (DP6) were formed as a consequence of the fructosyltransferase activity of Pectinex Ultra SP-L. The optimal reaction conditions for the synthesis of penta- and hexasaccharides were 60 degrees C, pH 5.5, 600 mg/mL stachyose, and 34 U/mL enzyme. Reaction time played an important role in oligosaccharide mixture composition constituted by 20% DP5, 0.7% DP6, 55% stachyose, 21% galactosyl-melibiose, and 1% monosaccharides after 1 h and 16% DP5, 4% DP6, 27% stachyose, 44% galactosyl-melibiose, and 2% monosaccharides after 3 h. In conclusion, stachyose could be used as a substrate for the enzymatic synthesis of new oligosaccharides that may open new opportunities in the development of future prebiotics.

  DOI：

  10.1021/jf202472p

文献信息

• Identification of Oligosaccharides Formed during Stachyose Hydrolysis by Pectinex Ultra SP-L
  作者：Antonia Montilla、Nieves Corzo、Agustin Olano、María Luisa Jimeno

  DOI：10.1021/jf900309x

  日期：2009.6.10

  The commercial enzyme preparation Pectinex Ultra SP-L containing fructosyltransferase activity was used to hydrolyze stachyose. During this reaction, besides the formation of mono-, di-, and trisaccharides (DP3), the presence of one pentasaccharide (DP5) and a new oligosaccharide (DP6) has been detected by gas chromatography. DP5 and DP6 oligosaccharides were isolated and fully characterized for the first time by an extensive nuclear magnetic resonance (NMR) study. Complete structure elucidation and full proton and carbon assignments were carried out using 1D (H-1, C-13) and 2D (gCOSY, multiplicity-edited gHSQC, gHSQC-TOCSY, and gHMBC) NMR experiments. The two oligosaccharides were shown to be stachyose-based structures; the pentasaccharide has a fructose unit linked to the C-1 of the fructose end of stachyose, and the hexasaccharide has a fructose unit linked to the C-1 of the fructose end of the pentasaccharide. The fructosyltransferase activity present in Pectinex Ultra SP-L allows new uses of this commercial enzyme preparation in the synthesis of oligosaccharides derived from alpha-galactosides.
• Study of Influential Factors on Oligosaccharide Formation by Fructosyltransferase Activity during Stachyose Hydrolysis by Pectinex Ultra SP-L
  作者：Antonia Montilla、Agustín Olano、Cristina Martínez-Villaluenga、Nieves Corzo

  DOI：10.1021/jf202472p

  日期：2011.10.12

  The influence of reaction conditions for oligosaccharide synthesis from stachyose using a commercial enzymatic preparation from Aspergillus aculeatus (Pectinex Ultra SP-L) was studied. Oligosaccharides were analyzed by gas chromatography with flame ionization detection (GC-FID) and matrix-assisted laser desorption/ionization-time-of-flight-mass spectrometry (MALDI-TOF-MS). Galactosyl-melibiose (DP3) was synthesized as a result of fructosidase activity, whereas fructosyl-stachyose (DP5) and difructosyl-stachyose (DP6) were formed as a consequence of the fructosyltransferase activity of Pectinex Ultra SP-L. The optimal reaction conditions for the synthesis of penta- and hexasaccharides were 60 degrees C, pH 5.5, 600 mg/mL stachyose, and 34 U/mL enzyme. Reaction time played an important role in oligosaccharide mixture composition constituted by 20% DP5, 0.7% DP6, 55% stachyose, 21% galactosyl-melibiose, and 1% monosaccharides after 1 h and 16% DP5, 4% DP6, 27% stachyose, 44% galactosyl-melibiose, and 2% monosaccharides after 3 h. In conclusion, stachyose could be used as a substrate for the enzymatic synthesis of new oligosaccharides that may open new opportunities in the development of future prebiotics.
• Seven new pentasaccharides from the roots of <i>Rehmannia glutinosa</i>
  作者：Yan-Fei Liu、Jie Zhou、Wan-Qi Zhang、Guo-Ru Shi、Xin-Yue Li、Ming-Hui Sun、Yi-Peng Zhao、Ruo-Yun Chen、De-Quan Yu

  DOI：10.1080/10286020.2023.2184356

  日期：——

  Abstract Seven new pentasaccharides (1–7), rehmaglupentasaccharides A-G, were isolated from the air-dried roots of Rehmannia glutinosa. Their structures were established from the spectroscopic data obtained and by chemical evidence. The known verbascose (8) and stachyose (9) were also obtained in the current investigation, and the structure of stachyose was unequivocally defined using X-ray diffraction

   抽象的 从地黄的风干根中分离出七种新的五糖 ( 1 – 7 )，即红葡五糖 AG。它们的结构是根据获得的光谱数据和化学证据确定的。在当前的研究中还获得了已知的毛蕊花糖 ( 8 ) 和水苏糖 ( 9 )，并且使用 X 射线衍射数据明确地定义了水苏糖的结构。测试了化合物1 – 9对五种人类肿瘤细胞系的细胞毒性、对多巴胺受体激活的影响以及对罗伊氏乳杆菌的增殖作用。