对香豆醇4-O-葡萄糖苷 | 120442-73-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 对香豆醇4-O-葡萄糖苷
• 英文名称: (E)-4-hydroxycinnamyl alcohol 4-O-β-D-glucopyranoside
• 英文别名: p-Coumaryl alcohol 4-O-glucoside；(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-[(E)-3-hydroxyprop-1-enyl]phenoxy]oxane-3,4,5-triol
• CAS: 120442-73-1
• 化学式: C₁₅H₂₀O₇
• 分子量: 312.32
• InChiKey: CRVXJSNSTGEXDX-HHMSBIESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  120
• 氢给体数：
  5
• 氢受体数：
  7

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  对香豆醇4-O-葡萄糖苷 在 sodium acetate buffer 作用下， 生成 4-(3-羟基丙-1-烯基)苯酚
  参考文献：
  名称：

  Arabidopsis thaliana β-Glucosidases BGLU45 and BGLU46 hydrolyse monolignol glucosides

  摘要：

  In higher plants, beta-glucosidases belonging to glycoside hydrolase (GH) Family 1 have been implicated in several fundamental processes including lignification. Phylogenetic analysis of Arabidopsis thaliana GH Family 1 has revealed that At1g61810 (BGLU45), At1g61820 (BGLU46), and At4g21760 (BGLU47) cluster with Pinus contorta coniferin beta-glucosidase, leading to the hypothesis that their respective gene products may be involved in lignification by hydrolysing monolignol glucosides. To test this hypothesis, we cloned cDNAs encoding BGLU45 and BGLU46 and expressed them in Pichia pastoris. The recombinant enzymes were purified to apparent homogeneity by ammonium sulfate fractionation and hydrophobic interaction chromatography. Among natural substrates tested, BGLU45 exhibited narrow specificity toward the monolignol glucosides syringin (K-m, 5.1 mM), coniferin (K-m, 7 mM), and p-coumaryl glucoside, with relative hydrolytic rates of 100%, 87%, and 7%, respectively. BGLU46 exhibited broader substrate specificity, cleaving salicin (100%), p-coumaryl glucoside (71%; K-m, 2.2mM), phenyl-beta-D-glucoside (62%), coniferin (8%), syringin (6%), and arbutin (6%). Both enzymes also hydrolysed p- and o-nitrophenyl-beta-D-glucosides. Using RT-PCR, we showed that BGLU45 and BGLU46 are expressed strongly in organs that are major sites of lignin deposition. In inflorescence stems, both genes display increasing levels of expression from apex to base, matching the known increase in lignification. BGLU45, but not BGLU46, is expressed in siliques, whereas only BGLU46 is expressed in roots. Taken together with recently described monolignol glucosyltransferases [Lim et al., J. Biol. Chem. (2001) 276, 4344-4349], our enzymological and molecular data support the possibility of a monolignol glucoside/beta-glucosidase system in Arabidopsis lignification. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2006.05.022
• 作为产物：
  描述：

  1,2,3,4,6-alpha-D-葡萄糖五乙酸酯 在 sodium tetrahydroborate 、 氢溴酸 、 溴 、 sodium methylate 、 potassium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 102.5h， 生成 对香豆醇4-O-葡萄糖苷
  参考文献：
  名称：

  Coniferin and Derivatives: a Fast and Easy Synthesis via the Aldehyde Series Using Phase-Transfer Catalysis

  摘要：

  在温和条件下，苯丙素以良好的收率（从香草醛出发为56%）合成。通过一锅反应将糖苷化反应与维蒂格反应耦合，生成了香豆醛四-O-乙酰糖苷，可以通过氢化钠轻易还原成四-O-乙酰苯丙素。类似的步骤也用于合成杉木苷和4-香豆醇的糖苷。

  DOI：

  10.1055/s-1998-2009

文献信息

• Freudenberg; Gehrke, Chemische Berichte, 1951, vol. 84, p. 443,450
  作者：Freudenberg、Gehrke

  DOI：——

  日期：——
• Agrawal, Babita; Singh, Journal of the Indian Chemical Society, 2010, vol. 87, # 9, p. 1143 - 1144
  作者：Agrawal, Babita、Singh

  DOI：——

  日期：——
• Coniferin and Derivatives: a Fast and Easy Synthesis via the Aldehyde Series Using Phase-Transfer Catalysis
  作者：Nicolas Daubresse、Charlette Francesch、Farida Mhamdi、Christian Rolando

  DOI：10.1055/s-1998-2009

  日期：1998.2

  Coniferin was synthesised in good yields (56% starting from vanillin) under mild conditions. A one-pot coupling of the glucosidation and Wittig-type reactions led to coniferaldehyde tetra-O-acetylglucoside, easily reduced into tetra-O-acetylconiferin by sodium borohydride. Similar procedures were used for the synthesis of syringin and the glucoside of 4-coumaryl alcohol.

  在温和条件下，苯丙素以良好的收率（从香草醛出发为56%）合成。通过一锅反应将糖苷化反应与维蒂格反应耦合，生成了香豆醛四-O-乙酰糖苷，可以通过氢化钠轻易还原成四-O-乙酰苯丙素。类似的步骤也用于合成杉木苷和4-香豆醇的糖苷。
• Arabidopsis thaliana β-Glucosidases BGLU45 and BGLU46 hydrolyse monolignol glucosides
  作者：Luis L. Escamilla-Treviño、Wei Chen、Marcella L. Card、Ming-Che Shih、Chi-Lien Cheng、Jonathan E. Poulton

  DOI：10.1016/j.phytochem.2006.05.022

  日期：2006.8

  In higher plants, beta-glucosidases belonging to glycoside hydrolase (GH) Family 1 have been implicated in several fundamental processes including lignification. Phylogenetic analysis of Arabidopsis thaliana GH Family 1 has revealed that At1g61810 (BGLU45), At1g61820 (BGLU46), and At4g21760 (BGLU47) cluster with Pinus contorta coniferin beta-glucosidase, leading to the hypothesis that their respective gene products may be involved in lignification by hydrolysing monolignol glucosides. To test this hypothesis, we cloned cDNAs encoding BGLU45 and BGLU46 and expressed them in Pichia pastoris. The recombinant enzymes were purified to apparent homogeneity by ammonium sulfate fractionation and hydrophobic interaction chromatography. Among natural substrates tested, BGLU45 exhibited narrow specificity toward the monolignol glucosides syringin (K-m, 5.1 mM), coniferin (K-m, 7 mM), and p-coumaryl glucoside, with relative hydrolytic rates of 100%, 87%, and 7%, respectively. BGLU46 exhibited broader substrate specificity, cleaving salicin (100%), p-coumaryl glucoside (71%; K-m, 2.2mM), phenyl-beta-D-glucoside (62%), coniferin (8%), syringin (6%), and arbutin (6%). Both enzymes also hydrolysed p- and o-nitrophenyl-beta-D-glucosides. Using RT-PCR, we showed that BGLU45 and BGLU46 are expressed strongly in organs that are major sites of lignin deposition. In inflorescence stems, both genes display increasing levels of expression from apex to base, matching the known increase in lignification. BGLU45, but not BGLU46, is expressed in siliques, whereas only BGLU46 is expressed in roots. Taken together with recently described monolignol glucosyltransferases [Lim et al., J. Biol. Chem. (2001) 276, 4344-4349], our enzymological and molecular data support the possibility of a monolignol glucoside/beta-glucosidase system in Arabidopsis lignification. (c) 2006 Elsevier Ltd. All rights reserved.