4-hydroxyphenyl-β-D-fructofuranoside | 444200-43-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-hydroxyphenyl-β-D-fructofuranoside
• 英文别名: (2S,3S,4S,5R)-2,5-bis(hydroxymethyl)-2-(4-hydroxyphenoxy)oxolane-3,4-diol
• CAS: 444200-43-5
• 化学式: C₁₂H₁₆O₇
• 分子量: 272.255
• InChiKey: KOTHHACKJKOJIJ-WISYIIOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  120
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  对苯二酚 、 蔗糖 在 Bacillus subtilis levansucrase 作用下， 生成 4-hydroxyphenyl-β-D-fructofuranoside
  参考文献：
  名称：

  Enzymatic fructosylation of aromatic and aliphatic alcohols by Bacillus subtilis levansucrase: Reactivity of acceptors

  摘要：

  Levansucrases from Bacillus subtilis (BS-LVS) and Leuconostoc mesenteroides ssp. mesenteroides ATCC 8293 (LevC), inulosucrase from Leuconostoc citreum (IslA) and an invertase from Saccharomyces cerevisiae (Inv) were evaluated in acceptor reactions with non-sugar acceptors. Among them, BS-LVS was selected for the fructosylation of aromatic or aliphatic alcohols due to its high activity and stability. The effects of acceptor concentration, enzyme concentration and the presence of a co-solvent in the fructosylation efficiency of hydroquinone were evaluated. It was demonstrated that this reaction is kinetically controlled, producing the best yields of phenolic fructosides when 500 mM of acceptor and 5 U mL(-1) of enzyme were employed. Higher enzyme loads resulted in the rapid hydrolysis of the products. Increased amounts of organic co-solvent up to 50% (v/v) reduced fructoside yield due to a concomitant decrease in the thermodynamic activity of the acceptor, as confirmed by theoretical calculations using COSMO-RS; moreover, increased fructose transfer to levan and reduced hydrolysis were observed. It was found that BS-LVS preferentially fructosylates aromatic over aliphatic alcohols. A maximum fructoside production (19-35 mM) was obtained with dihydroxybenzene acceptors such as hydroquinone, whereas reactions with primary alcohols, such as benzyl alcohol resulted in lower fructosylation efficiency. This selectivity was also demonstrated by the fact that 4-hydroxybenzylalcohol, a bifunctional acceptor, was fructosylated at a rate ten times faster on its aromatic hydroxyl group. BS-LVS selectivity over phenol fructosylation was inversely correlated with the acceptor pK(a) value. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2011.02.002

文献信息

• Enzymatic fructosylation of aromatic and aliphatic alcohols by Bacillus subtilis levansucrase: Reactivity of acceptors
  作者：Arlette Mena-Arizmendi、Joel Alderete、Sergio Águila、Alain Marty、Alfonso Miranda-Molina、Agustín López-Munguía、Edmundo Castillo

  DOI：10.1016/j.molcatb.2011.02.002

  日期：2011.6

  Levansucrases from Bacillus subtilis (BS-LVS) and Leuconostoc mesenteroides ssp. mesenteroides ATCC 8293 (LevC), inulosucrase from Leuconostoc citreum (IslA) and an invertase from Saccharomyces cerevisiae (Inv) were evaluated in acceptor reactions with non-sugar acceptors. Among them, BS-LVS was selected for the fructosylation of aromatic or aliphatic alcohols due to its high activity and stability. The effects of acceptor concentration, enzyme concentration and the presence of a co-solvent in the fructosylation efficiency of hydroquinone were evaluated. It was demonstrated that this reaction is kinetically controlled, producing the best yields of phenolic fructosides when 500 mM of acceptor and 5 U mL(-1) of enzyme were employed. Higher enzyme loads resulted in the rapid hydrolysis of the products. Increased amounts of organic co-solvent up to 50% (v/v) reduced fructoside yield due to a concomitant decrease in the thermodynamic activity of the acceptor, as confirmed by theoretical calculations using COSMO-RS; moreover, increased fructose transfer to levan and reduced hydrolysis were observed. It was found that BS-LVS preferentially fructosylates aromatic over aliphatic alcohols. A maximum fructoside production (19-35 mM) was obtained with dihydroxybenzene acceptors such as hydroquinone, whereas reactions with primary alcohols, such as benzyl alcohol resulted in lower fructosylation efficiency. This selectivity was also demonstrated by the fact that 4-hydroxybenzylalcohol, a bifunctional acceptor, was fructosylated at a rate ten times faster on its aromatic hydroxyl group. BS-LVS selectivity over phenol fructosylation was inversely correlated with the acceptor pK(a) value. (C) 2011 Elsevier B.V. All rights reserved.