(R)-Vicianin

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-Vicianin
• 英文别名: (2R)-2-phenyl-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxyacetonitrile
• 化学式: C₁₉H₂₅NO₁₀
• 分子量: 427.4
• InChiKey: YYYCJNDALLBNEG-HTSYZHAISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  182
• 氢给体数：
  6
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (R)-Vicianin 、 水 生成 扁桃腈 、 vicianose
  参考文献：
  名称：

  Catabolism of Cyanogenic Glycosides by Purified Vicianin Hydrolase from Squirrel's Foot Fern (Davallia Trichomanoides Blume)

  摘要：

  利用 DEAE-纤维素和 Ultrogel HA 色谱法，从松鼠脚蕨类植物（Davallia trichomanoides Blume）的嫩叶和蕨头上广泛纯化了藤黄素水解酶，该酶催化藤黄素（K m，4.9 毫摩尔）在最佳 pH 值为 5.5 时水解为（R）-扁桃腈和藤黄素。该酶的原生分子量为 340,000，等电点为 4.6 至 4.7。SDS-PAGE 分析得出了三种多肽，分子量分别为 56,000、49,000 和 32,500。该酶只水解范围较窄的苷类，在氰苷类化合物中，它对 (R)-epimers 有严格的要求，对双糖的偏好高于单糖。(R)-苦杏仁苷、(R)-樱桃苷和对硝基苯基-β-d-葡萄糖苷的水解速度分别为葡萄苷水解速度的 27%、14% 和 3%。混合底物研究表明，(R)-藤黄素、(R)-樱黄素和对硝基苯基-β-d-葡萄糖苷竞争同一个活性位点。蓖麻毒素、δ-葡萄糖酸内酯和对氯巯基苯磺酸盐对该酶有明显的抑制作用。该酶不能识别 concanavalin A-Sepharose 4B，也不能用周期性酸-Schiff 试剂染色，这表明该酶不是糖蛋白。

  DOI：

  10.1104/pp.86.2.322

文献信息

• Catabolism of Cyanogenic Glycosides by Purified Vicianin Hydrolase from Squirrel's Foot Fern (<i>Davallia Trichomanoides</i> Blume)
  作者：Pauline A. Lizotte、Jonathan E. Poulton

  DOI：10.1104/pp.86.2.322

  日期：1988.2.1

  Vicianin hydrolase, which catalyzes the hydrolysis of vicianin (K  m, 4.9 millimolar) to (R)-mandelonitrile and vicianose at an optimum pH of 5.5, was extensively purified from the young fronds and fiddleheads of the squirrel's foot fern (Davallia trichomanoides Blume) using DEAE-cellulose and Ultrogel HA chromatography. The native molecular weight of the enzyme was 340,000, and the isoelectric point was 4.6 to 4.7. SDS-PAGE analysis yielded three polypeptides with molecular weights of 56,000, 49,000, and 32,500. The enzyme hydrolyzed only a narrow range of glycosides and, among cyanogenic glycosides, exhibited a strict requirement for (R)-epimers and a preference for disaccharides over monosaccharides. (R)-Amygdalin, (R)-prunasin and p-nitrophenyl-β-d-glucoside were hydrolyzed at 27, 14, and 3%, respectively, of the rate of vicianin hydrolysis. Mixed substrate studies showed that (R)-vicianin, (R)-prunasin, and p-nitrophenyl-β-d-glucoside competed for the same active site. The enzyme was significantly inhibited by castanospermine, δ-gluconolactone, and p-chloromercuriphenylsulfonate. Failure to recognize concanavalin A-Sepharose 4B and to stain with periodic acid-Schiff reagent indicated that the enzyme was not a glycoprotein.

  利用 DEAE-纤维素和 Ultrogel HA 色谱法，从松鼠脚蕨类植物（Davallia trichomanoides Blume）的嫩叶和蕨头上广泛纯化了藤黄素水解酶，该酶催化藤黄素（K m，4.9 毫摩尔）在最佳 pH 值为 5.5 时水解为（R）-扁桃腈和藤黄素。该酶的原生分子量为 340,000，等电点为 4.6 至 4.7。SDS-PAGE 分析得出了三种多肽，分子量分别为 56,000、49,000 和 32,500。该酶只水解范围较窄的苷类，在氰苷类化合物中，它对 (R)-epimers 有严格的要求，对双糖的偏好高于单糖。(R)-苦杏仁苷、(R)-樱桃苷和对硝基苯基-β-d-葡萄糖苷的水解速度分别为葡萄苷水解速度的 27%、14% 和 3%。混合底物研究表明，(R)-藤黄素、(R)-樱黄素和对硝基苯基-β-d-葡萄糖苷竞争同一个活性位点。蓖麻毒素、δ-葡萄糖酸内酯和对氯巯基苯磺酸盐对该酶有明显的抑制作用。该酶不能识别 concanavalin A-Sepharose 4B，也不能用周期性酸-Schiff 试剂染色，这表明该酶不是糖蛋白。
• Compositions and methods for treating infectious disease
  申请人：Sichtnik Laszlo

  公开号：US10183964B2

  公开（公告）日：2019-01-22

  Provided are cyanogenic compositions for treating diseases, such as infectious diseases.

  本发明提供了用于治疗疾病（如传染性疾病）的生氰组合物。
• COMPOSITIONS AND METHODS FOR TREATING INFECTIOUS DISEASE
  申请人：Sichtnik Laszlo

  公开号：US20190144483A1

  公开（公告）日：2019-05-16

  Provided are cyanogenic compositions for treating diseases, such as infectious diseases.
• Vicianin Hydrolase is a Novel Cyanogenic  -Glycosidase Specific to  -Vicianoside (6-O- -L-Arabinopyranosyl- -D-Glucopyranoside) in Seeds of Vicia angustifolia
  作者：Y. O. Ahn、H. Saino、M. Mizutani、B.-i. Shimizu、K. Sakata

  DOI：10.1093/pcp/pcm065

  日期：——

  The cyanogenic disaccharide glycoside, vicianin [mandelonitrile β-vicianoside (6-O-α-l-arabinopyranosyl-β-d-glucopyranoside)], is accumulated in seeds of Vicia angustifolia var. segetalis. Vicianin hydrolase (VH) catalyzes the hydrolysis of vicianin into mandelonitrile and a disaccharide vicianose. VH was purified from the seeds using DEAE-, CM- and Con A-Sepharose chromatography, and the molecular mass of the purified VH was estimated to be 56 kDa on SDS–PAGE. The N-terminal amino acid sequence of the purified VH was determined, and a cDNA encoding VH was obtained. The deduced VH protein consists of a 509 amino acid polypeptide containing a putative secretion signal peptide. It shares about 50% identity with various kinds of plant β-glycosidases including tea leaf β-primeverosidase and furcatin hydrolase, and is classified in family 1 of the glycosyl hydrolases. The VH transcript was detected abundantly in seeds and moderately in flowers, but only slightly in leaves, stems and roots, indicating that the organ distribution of VH expression is similar to that of the substrate vicianin. The recombinant VH was produced in insect cells with a baculovirus system, and was compared with the native VH in terms of substrate specificity. Both enzymes hydrolyzed vicianin to release vicianose, demonstrating that VH is a disaccharide-specific β-glycosidase. VH also hydrolyzed the mandelonitrile β-glucoside prunasin to some extent but did not hydrolyze the gentiobioside amygdalin, both of which contain the same aglycone as vicianin. Thus, VH is a unique cyanogenic glycosidase showing high glycone specificity for the disaccharide vicianoside.

  藜芦苷（扁豆苷）是一种氰基二糖苷，存在于藜芦（Vicia angustifolia var. segetalis）的种子中。藜芦苷水解酶（VH）催化藜芦苷水解为扁豆腈和二糖藜芦糖。使用DEAE-、CM-和Con A-Sepharose色谱法从种子中纯化了VH，SDS-PAGE分析显示纯化VH的分子质量约为56 kDa。确定了纯化VH的N端氨基酸序列，并获得了编码VH的cDNA。推测的VH蛋白由509个氨基酸组成的多肽，包含一个推测的分泌信号肽。它与各种植物β-糖苷酶（包括茶叶β-樱草糖苷酶和叉糖苷酶）的同源性约为50%，属于糖苷水解酶家族1。VH转录物在种子中大量存在，在花中中等存在，但在叶、茎和根中仅少量存在，表明VH的表达器官分布与底物藜芦苷的分布相似。用杆状病毒系统在昆虫细胞中生产了重组VH，并与天然VH进行了底物特异性比较。两种酶都能水解藜芦�