(R)-2,3-dihydroxypropyl 5-deoxy-5-dimethylarsino-2,3-O-isopropylidene-β-D-riboside | 370860-12-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-2,3-dihydroxypropyl 5-deoxy-5-dimethylarsino-2,3-O-isopropylidene-β-D-riboside
• 英文别名: (2R)-3-[[(3aR,4R,6S,6aS)-6-(dimethylarsanylmethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]oxy]propane-1,2-diol
• CAS: 370860-12-1
• 化学式: C₁₃H₂₅AsO₆
• 分子量: 352.26
• InChiKey: CDRDVHRDLAVJSH-LZQZFOIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.36
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (R)-2,3-dihydroxypropyl 5-deoxy-5-dimethylarsino-2,3-O-isopropylidene-β-D-riboside 在 双氧水 、 三氟乙酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.67h， 生成 (2'R)-2',3'-dihydroxypropyl 5-deoxy-5-(dimethylarsinoyl)-β-D-riboside
  参考文献：
  名称：

  摘要：

  An efficient synthesis of (R)-2,3-dihydroxypropyl 5-deoxy-5-dimethylarsinyl-beta -D-riboside, a common marine arsenical, from D-ribose, (S)-2,3-dibenzyloxypropanol and iododimethylarsine is described.

  DOI：

  10.1071/ch01036
• 作为产物：
  描述：

  1-甲氧基-2,3-O-异亚丙基-5-O-对甲苯磺酰基-beta-D-呋喃核糖苷 在 camphor-10-sulfonic acid 、 四丁基氯化铵 、 氨 、 sodium 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， -78.0~80.0 ℃ 、3.33 kPa 条件下， 反应 61.5h， 生成 (R)-2,3-dihydroxypropyl 5-deoxy-5-dimethylarsino-2,3-O-isopropylidene-β-D-riboside
  参考文献：
  名称：

  摘要：

  An efficient synthesis of (R)-2,3-dihydroxypropyl 5-deoxy-5-dimethylarsinyl-beta -D-riboside, a common marine arsenical, from D-ribose, (S)-2,3-dibenzyloxypropanol and iododimethylarsine is described.

  DOI：

  10.1071/ch01036

文献信息

• Do Arsenosugars Pose a Risk to Human Health? The Comparative Toxicities of a Trivalent and Pentavalent Arsenosugar
  作者：Paul Andrewes、David M. DeMarini、Kunihiro Funasaka、Kathleen Wallace、Vivian W. M. Lai、Hongsui Sun、William R. Cullen、Kirk T. Kitchin

  DOI：10.1021/es035440f

  日期：2004.8.1

  Seafood frequently contains high concentrations of arsenic (similar to10-100 mg/kg dry weight). In marine algae (seaweed), this arsenic occurs predominantly as ribose derivatives known collectively as arsenosugars. Although it is clear that arsenosugars are not acutely toxic, there is a possibility of arsenosugars having slight chronic toxicity. In general, trivalent arsenicals are more toxic than their pentavalent counterparts, so in this work we examine the hypothesis that trivalent arsenosugars might be significantly more toxic than pentavalent arsenosugars in vitro. We compared the in vitro toxicity of (R)-2,3-dihydroxypropyl-5-deoxy-5-dimethylarsinoyl-beta-D-riboside, a pentavalent arsenosugar, to that of its trivalent counterpart, (R)-2,3-dihydroxypropyl-5-deoxy-5-dimethylarsino-beta-D- riboside. The trivalent arsenosugar nicked plasmid DNA, whereas the pentavalent arsenosugar did not. The trivalent arsenosugar was more cytotoxic (IC50 = 200 muM, 48 h exposure) than its pentavalent counterpart (IC50 > 6000 muM, 48 h exposure) in normal human epidermal keratinocytes in vitro as determined via the neutral red uptake assay. However, both the trivalent and the pentavalent arsenosugars were significantly less toxic than MMA(III), DMA(III), and arsenate. Neither the pentavalent arsenosugar nor the trivalent arsenosugar were mutagenic in Salmonella TA104. The trivalent arsenosugar was readily formed by reaction of the pentavalent arsenosugar with thiol compounds, including, cysteine, glutathione, and dithioerythritol. This work suggests that the reduction of pentavalent arsenosugars to trivalent arsenosugars in biology might have environmental consequences, especially because seaweed consumption is a significant environmental source for human exposure to arsenicals.
• ——
  作者：Robert V. Stick、Keith A. Stubbs、D. Matthew G. Tilbrook

  DOI：10.1071/ch01036

  日期：——

  An efficient synthesis of (R)-2,3-dihydroxypropyl 5-deoxy-5-dimethylarsinyl-beta -D-riboside, a common marine arsenical, from D-ribose, (S)-2,3-dibenzyloxypropanol and iododimethylarsine is described.