bifructosyl-β(2,6)-puerarin | 1372702-85-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: bifructosyl-β(2,6)-puerarin
• 英文别名: β-D-difructofuranosyl-(2→6)-puerarin；8-[(2S,3R,4R,5S,6R)-6-[[(2R,3S,4S,5R)-5-[[(2R,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4-dihydroxy-2-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]-7-hydroxy-3-(4-hydroxyphenyl)chromen-4-one
• CAS: 1372702-85-6
• 化学式: C₃₃H₄₀O₁₉
• 分子量: 740.669
• InChiKey: JHZMUTAYOWZNHQ-KTLOPNRMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.7
• 重原子数：
  52
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  315
• 氢给体数：
  12
• 氢受体数：
  19

反应信息

• 作为产物：
  描述：

  葛根素 、 蔗糖 在 Levansucrase from Gluconacetobacter diazotrophicus SRT₄ 作用下， 以 aq. buffer 为溶剂， 反应 24.0h， 生成 monofructosyl-β(2,6)-puerarin 、 bifructosyl-β(2,6)-puerarin
  参考文献：
  名称：

  One-pot bi-enzymatic cascade synthesis of puerarin polyfructosides

  摘要：

  Enzymatic glycosylation is an efficient way to increase the water solubility and the bioavailability of flavonoids. Levansucrases from Bacillus subtilis (Bs_SacB), Gluconacetobacter diazotrophicus (Gd_LsdA), Leuconostoc mesenteroides (Lm_LevS) and Zymomonas mobilis (Zm_LevU) were screened for puerarin (daidzein-8-C-glucoside) fructosylation. Gd_LsdA transferred the fructosyl unit of sucrose onto the glucosyl unit of the acceptor forming beta-D-fructofuranosyl-(2 -> 6)-puerarin (P1a), while Bs_SacB, Lm_LevS and Zm_LevU synthesized puerarin-4'-O-beta-D-fructofuranoside (P1b) and traces of P1a. The Gd_LsdA product P1a was purified and assayed as precursor for the synthesis of puerarin polyfructosides (PPFs). Bs_SacB elongated P1a more competently forming a linear series of water-soluble PPFs reaching at least 21 fructosyl units, as characterized by HPLC-UV-MS, HPSEC and MALDI-TOF-MS. Simultaneous or sequential Gd_LsdA/Bs_SacB reactions yielded PPFs directly from puerarin with the acceptor conversion ranging 82-92 %. The bi-enzymatic cascade synthesis of PPFs in the same reactor avoided the isolation of the intermediate product P1a and it is appropriate for use at industrial scale.

  DOI：

  10.1016/j.carbpol.2020.116710