alizarin-2-O-β-D-glucopyranoside | 31297-82-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: alizarin-2-O-β-D-glucopyranoside
• 英文别名: 1-Hydroxy-2-(beta-D-glucosyloxy)-9,10-anthraquinone；1-hydroxy-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyanthracene-9,10-dione
• CAS: 31297-82-2
• 化学式: C₂₀H₁₈O₉
• 分子量: 402.358
• InChiKey: LPUCQUKLBVSNAF-UJXPUUNTSA-N

物化性质

• 熔点：
  237 °C
• 沸点：
  722.4±60.0 °C(Predicted)
• 密度：
  1.645±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  154
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  alizarin-2-O-β-D-glucopyranoside 在 甲醇 、 氨 作用下， 生成 2-β-D-glucopyranosyloxy-1-hydroxy-anthraquinone-9-imine
  参考文献：
  名称：

  Zemplen; Mueller, Chemische Berichte, 1929, vol. 62, p. 2107,2112

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2-二羟基蒽醌 在 喹啉 、 sodium hydroxide 、 silver(l) oxide 作用下， 生成 alizarin-2-O-β-D-glucopyranoside
  参考文献：
  名称：

  Zemplen; Mueller, Chemische Berichte, 1929, vol. 62, p. 2107,2112

  摘要：

  DOI：

文献信息

• Novel alizarin-based chromogenic substrates, their uses and composition containing same
  申请人：——

  公开号：US20030082667A1

  公开（公告）日：2003-05-01

  The invention concerns a novel chromogenic substrate based on Alizarin. The invention also concerns the uses to which this substrate can be put, and a formulation containing such a substrate. It consists therefore of a substrate to detect the presence of an enzyme activity, with the following general formula: 1 in which: the two ketone groups of the central ring can be replaced by one group R 11 (in the upper position), and by OH (in the lower position). R 1 is a target part or H, and R 2 is a target part or H, with at least one out of R 1 and R 2 being a target part, R 3 is H, SO 3 H, Cl, Br, F, I, NO 2 , NH 2 , NR 9 R 10 , or an Acylamino Aminoaryl or Aminoacylamino group of the type NHCOX, with X being an Alkyl, Aryl or Aralkyl group or an a-amino acid residue such as Alanine, R4 is H, SO 3 H, Cl, Br, F, I, NO 2 , NH 2 , NR 9 R 10 , OH or an Acylamino Aminoaryl or Aminoacylamino group of the type NHCOX, with X being an Alkyl, Aryl or Aralkyl group or an &agr;-amino acid such as Alanine, according to a modification, R 3 and R 4 form bonds with one another to create a ring with at least five sides, and preferably six sides. R 5 , R 6 , R 7 and R 8 each consist of one of the following atoms or groups of atoms: H, a halogen (particularly Cl or Br), OH, SO 3 H, or an Alkyl or Alkoxy group, and R 9 a R 10 are independently a Methyl, Alkyl, Aryl, Aralkyl group, or one (either R 9 or R 10 ) is a ring structure (Piperidine, Pyrrolidine, Morpholine, etc.) with the other (either R 10 or R 9 ) being a Hydrogen atom. The invention is particularly applicable in the field of diagnosis.

  这项发明涉及一种基于茜素的新型显色底物。该发明还涉及可以应用此底物的用途，以及含有这种底物的配方。因此，它包括一种用于检测酶活性存在的底物，具有以下一般公式：其中：中心环的两个酮基团可以被一个R11基团（在上部位置）和一个OH基团（在下部位置）取代。R1是目标部分或H，R2是目标部分或H，其中至少有一个是目标部分，R3是H、SO3H、Cl、Br、F、I、NO2、NH2、NR9R10或NHCOX类型的Acylamino Aminoaryl或Aminoacylamino基团，其中X是Alkyl、Aryl或Aralkyl基团或α-氨基酸残基，如丙氨酸，R4是H、SO3H、Cl、Br、F、I、NO2、NH2、NR9R10、OH或NHCOX类型的Acylamino Aminoaryl或Aminoacylamino基团，其中X是Alkyl、Aryl或Aralkyl基团或α-氨基酸，如丙氨酸，根据一种修改，R3和R4相互形成键，创建至少五边形，最好是六边形的环。R5、R6、R7和R8分别由以下原子或原子团组成：H、卤素（特别是Cl或Br）、OH、SO3H或Alkyl或Alkoxy基团，而R9和R10独立地是甲基、Alkyl、Aryl、Aralkyl基团，或者其中之一（R9或R10）是环结构（哌啶、吡咯烷、吗啉等），而另一个（R10或R9）是氢原子。该发明在诊断领域特别适用。
• On the Catalytic Activity of a GT1 Family Glycosyltransferase from <i>Streptomyces venezuelae</i> ISP5230
  作者：Stephanie M. Forget、Sydney B. Shepard、Ebrahim Soleimani、David L. Jakeman

  DOI：10.1021/acs.joc.9b01130

  日期：2019.9.20

  the discovery of a broad substrate scope with respect to both acceptor molecules and donor sugars. In addition to polyphenols, including anthraquinones, simple aromatics containing primary or secondary alcohols, a variety of complex natural products and synthetic drugs were glucosylated or xylosylated by Sv0189. Regioselectivity was established through the isolation and characterization of glucosylated

  鉴定了来自委内链霉菌ISP5230（ATCC 10721）的GT1家族糖基转移酶Sv0189 。重组产生的蛋白Sv0189具有UDP-糖基转移酶活性。使用非天然硝基苯基糖苷作为活化的供体的试验进行的筛选导致发现了关于受体分子和供体糖的广泛的底物范围。除了多酚（包括蒽醌），含有伯醇或仲醇的简单芳族化合物之外，Sv0189还对各种复杂的天然产物和合成药物进行了糖基化或木糖基化。通过糖基化产物的分离和表征来建立区域选择性。Sv0189和同源蛋白在链霉菌中广泛分布 物种及其明显的底物混杂性揭示了它们作为糖多样化生物催化剂的发展潜力。
• Novel chromogenic substrates based on Alizarin, their applications and formulations containing such substrates
  申请人：Armstrong Lyle

  公开号：US20060172364A1

  公开（公告）日：2006-08-03

  An alizarin-based chromogenic substrate, a composition containing the substrate, and its use to detect the presence of an enzymatic activity. The substrate is particularly applicable in the field of biological diagnosis.

  一种基于茜素的显色底物、含有该底物的组合物及其用于检测酶活性的用途。该底物特别适用于生物诊断领域。
• Takahashi, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1925, p. 969,982; dtsch. Ref. Nr. 525, S. 4
  作者：Takahashi

  DOI：——

  日期：——
• Synthesis of glycoside derivatives of hydroxyanthraquinone with ability to dissolve and inhibit formation of crystals of calcium oxalate. Potential compounds in kidney stone therapy
  作者：Anna Frąckowiak、Przemysław Skibiński、Wiesław Gaweł、Ewa Zaczyńska、Anna Czarny、Roman Gancarz

  DOI：10.1016/j.ejmech.2009.11.042

  日期：2010.3

  Synthesis of glycosyl derivatives of hydroxyanthraquinones (6-10) potentially useful for kidney stone therapy is presented. These compounds were analyzed as inhibitors of calcium oxalate crystals formation as well as substances with the ability of dissolving crystalline calcium oxalate. In addition, the effect of the compounds obtained on real kidney stones was analyzed by ex vivo tests. The tests on L929 and A545 cell lines have shown that the compounds obtained were not cytotoxic. (C) 2009 Elsevier Masson SAS. All rights reserved.