(+)-catechin 3'-O-α-D-glucopyranoside | 150337-42-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: (+)-catechin 3'-O-α-D-glucopyranoside
• 英文别名: (2R,3S)-2-[4-hydroxy-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-3,4-dihydro-2H-chromene-3,5,7-triol
• CAS: 150337-42-1
• 化学式: C₂₁H₂₄O₁₁
• 分子量: 452.415
• InChiKey: ZZTOVZGFHZQEAT-KLIUUODMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  190
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  蔗糖 、 儿茶提取物 在 3-吗啉丙磺酸 、 recombinant sucrose phosphorylase from Thermoanaerobacterium thermosaccharolyticum, mutant R₁₃₄A 作用下， 以 aq. buffer 为溶剂， 反应 24.0h， 以31.4%的产率得到(+)-catechin 3'-O-α-D-glucopyranoside
  参考文献：
  名称：

  Enzymatic Glycosylation of Phenolic Antioxidants: Phosphorylase-Mediated Synthesis and Characterization

  摘要：

  Although numerous biologically active molecules exist as glycosides in nature, information on the activity, stability, and solubility of glycosylated antioxidants is rather limited to date. In this work, a wide variety of antioxidants were glycosylated using different phosphorylase enzymes. The resulting antioxidant library, containing alpha/beta-glucosides, different regioisomers, cellobiosides, and cellotriosides, was then characterized. Glycosylation was found to significantly increase the solubility and stability of all evaluated compounds. Despite decreased radical-scavenging abilities, most glycosides were identified to be potent antioxidants, outperforming the commonly used 2,6-bis(1,1-dimethylethyl)-4-methylphenol (BHT). Moreover, the point of attachment, the anomeric configuration, and the glycosidic chain length were found to influence the properties of these phenolic glycosides.

  DOI：

  10.1021/acs.jafc.5b04380

文献信息

• Redesign of the Active Site of Sucrose Phosphorylase through a Clash-Induced Cascade of Loop Shifts
  作者：Michael Kraus、Clemens Grimm、Jürgen Seibel

  DOI：10.1002/cbic.201500514

  日期：2016.1

  Repositioning key loops by adding a clash‐inducing hydrophobic Phe—remodelling a sucrose phosphorylase into a polyphenol transglucosidase: Introducing a sterically demanding residue into the active site of a sucrose phosphorylase enlarged the active site through indirect effects arising from a cascade of conformational changes. Aromatic acceptors could thus be glucosylated.

  通过添加诱导冲突的疏水性Phe来重新定位关键环，从而将蔗糖磷酸化酶重塑为多酚转葡糖苷酶：将空间需求的残基引入蔗糖磷酸化酶的活性位点通过一系列构象变化产生的间接作用扩大了活性位点。芳香受体因此可以被糖基化。
• Enzymatic Synthesis of (+)Catechin-α-glucoside and Its Effect on Tyrosinase Activity
  作者：Masataka Funayama、Toyokazu Nishino、Akira Hirota、Sawao Murao、Shigeyuki Takenishi、Hirofumi Nakano

  DOI：10.1271/bbb.57.1666

  日期：1993.1

  The glycosidation of (+)catechin, which has five hydroxyl groups with cyclodextrin glucanotransferase (CGTase, EC 2.4.1.19) and soluble starch has been studied. One of the transfer products was purified and its structure was determined to be (+)catechin 3ʹ-0-α-D-glucopyranoside. This glucoside noncompetitively inhibited the activity of tyrosinase from mushroom, IC50 being 5.8 mM, but didn’t inhibit that from mouse melanoma. In contrast, arbutin (hydroquinone-0-β-D-glucopyranoside) inhibited both tyrosinases.

  研究了具有五个羟基的(+)儿茶素与环糊精葡聚糖转移酶（CGTase，EC 2.4.1.19）和可溶性淀粉的糖苷化反应。纯化了其中一种转移产物，并确定其结构为(+)儿茶素 3ʹ-0-α-D-吡喃葡萄糖苷。这种葡萄糖苷能非竞争性地抑制蘑菇中酪氨酸酶的活性，IC50 为 5.8 mM，但不能抑制小鼠黑色素瘤中酪氨酸酶的活性。相反，熊果苷（对苯二酚-0-β-D-吡喃葡萄糖苷）对两种酪氨酸酶都有抑制作用。
• Kitao, Satoshi; Ariga, Toshiaki; Matsudo, Takanao, Bioscience, Biotechnology and Biochemistry, 1993, vol. 57, # 12, p. 2010 - 2015
  作者：Kitao, Satoshi、Ariga, Toshiaki、Matsudo, Takanao、Sekime, Hiroshi

  DOI：——

  日期：——
• Enzymatic Glycosylation of Phenolic Antioxidants: Phosphorylase-Mediated Synthesis and Characterization
  作者：Karel De Winter、Griet Dewitte、Mareike E. Dirks-Hofmeister、Sylvie De Laet、Helena Pelantová、Vladimír Křen、Tom Desmet

  DOI：10.1021/acs.jafc.5b04380

  日期：2015.11.25

  Although numerous biologically active molecules exist as glycosides in nature, information on the activity, stability, and solubility of glycosylated antioxidants is rather limited to date. In this work, a wide variety of antioxidants were glycosylated using different phosphorylase enzymes. The resulting antioxidant library, containing alpha/beta-glucosides, different regioisomers, cellobiosides, and cellotriosides, was then characterized. Glycosylation was found to significantly increase the solubility and stability of all evaluated compounds. Despite decreased radical-scavenging abilities, most glycosides were identified to be potent antioxidants, outperforming the commonly used 2,6-bis(1,1-dimethylethyl)-4-methylphenol (BHT). Moreover, the point of attachment, the anomeric configuration, and the glycosidic chain length were found to influence the properties of these phenolic glycosides.