(4R,5R)-4-amino-1,2,5-decanetriol | 544684-41-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (4R,5R)-4-amino-1,2,5-decanetriol
• 英文别名: (4R,5R)-4-aminodecane-1,2,5-triol
• CAS: 544684-41-5
• 化学式: C₁₀H₂₃NO₃
• 分子量: 205.298
• InChiKey: NMBUEKDJGKWIEY-VXRWAFEHSA-N

物化性质

• 沸点：
  399.9±42.0 °C(Predicted)
• 密度：
  1.075±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  86.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R,5R)-4-amino-1,2,5-decanetriol 在 sodium periodate 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 水 、 二甲基亚砜 为溶剂， 生成 (6S,8R)-8-hydroxy-6-[(1R)-1-hydroxyhexyl]-3-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5,6,7,8-tetrahydropyrimido[1,2-a]purin-10-one
  参考文献：
  名称：

  Stereocontrolled Syntheses of All Four Stereoisomeric 1,N²-Deoxyguanosine Adducts of the Lipid Peroxidation Product trans-4-Hydroxynonenal

  摘要：

  [GRAPHICS]trans-4-Hydroxynonenal (4-HNE) is a unique product from the peroxidation of omega -6 polyunsaturated fatty acids. The major reaction of racemic 4-HNE with DNA is with deoxyguanosine to give four stereoisomeric exocyclic propano adducts. The stereospecific syntheses of these four adducts has been achieved at the nucleoside level. The synthetic approach is amenable to the synthesis of structurally defined oilgonucleotides containing these endogenous genotoxins.

  DOI：

  10.1021/ol016810c
• 作为产物：
  描述：

  (4R,5R)-4-(benzylamino)-1,2,5-decanetriol 在 palladium dihydroxide 氢气 作用下， 以 甲醇 为溶剂， 生成 (4R,5R)-4-amino-1,2,5-decanetriol
  参考文献：
  名称：

  含脂质过氧化产物trans-4-Hydroxynonenal的立体化学定义的1,N2-脱氧鸟苷加合物的寡核苷酸的定点合成和反应性

  摘要：

  trans-4-Hydroxynonenal (HNE) 是 omega-6 多不饱和脂肪酸的主要过氧化产物。HNE 与 DNA 的反应产生了四种非对映异构体 1,N(2)-γ-羟基丙酸脱氧鸟苷加合物；在动物组织中检测到这些加合物的背景水平。这四种加合物在核苷水平上的立体有择合成已经完成。此外，还开发了一种将它们定点掺入寡核苷酸的通用策略。与未加合物链相比，这些加合物是不稳定的，通过熔融温度测量。加合物 12 聚体的热失稳范围为 5 到 16 摄氏度，取决于加合物的绝对立体化学。还检查了 HNE 加合物在掺入 CpG 序列时形成链间 DNA-DNA 交联的能力。我们发现只有一种 HNE 立体异构体形成链间 DNA-DNA 交联。

  DOI：

  10.1021/ja0288800

文献信息

• Simplified synthesis of individual stereoisomers of the 4-hydroxynonenal adducts of deoxyguanosine
  作者：Plamen P. Christov、Edward K. Hawkins、Nathan R. Kett、Carmelo J. Rizzo

  DOI：10.1016/j.tetlet.2013.06.004

  日期：2013.8

  We previously reported the synthesis of the 1,N-2-deoxyguanosine adducts of 4-hydroxynonenal, an important product of lipid peroxidation, which involved the nucleophilic aromatic substitution reaction of O-6-protected-2-fluoroinosine with 4-amino-1,2,5-trihydroxydecanal followed by periodate oxidation of the vicinal diol.(6) An improved synthesis of the amino triols has been developed. The syn and anti diastereomers of a key intermediate, 4-nitro-5-hydroxy-1-decene, were synthesized by a Henry reaction and separated; each diastereomer was further separated into individual enantiomers by chiral supercritical fluid chromatography. Of note, dihydroxylation of the terminal olefin under conventional conditions with catalytic OsO4 and a tertiary amine oxide as the stoichiometric oxidant led to scrambling of stereochemistry of the nitro group. The scrambling was not observed when t-butylhydroperoxide was used as the oxidant. (C) 2013 Elsevier Ltd. All rights reserved.
• Site-Specific Synthesis and Reactivity of Oligonucleotides Containing Stereochemically Defined 1,<i>N</i>²-Deoxyguanosine Adducts of the Lipid Peroxidation Product <i>trans</i>-4-Hydroxynonenal
  作者：Hao Wang、Ivan D. Kozekov、Thomas M. Harris、Carmelo J. Rizzo

  DOI：10.1021/ja0288800

  日期：2003.5.1

  is a major peroxidation product of omega-6 polyunsaturated fatty acids. The reaction of HNE with DNA gives four diastereomeric 1,N(2)-gamma-hydroxypropano adducts of deoxyguanosine; background levels of these adducts have been detected in animal tissue. Stereospecific syntheses of these four adducts at the nucleoside level have been accomplished. In addition, a versatile strategy for their site-specific

  trans-4-Hydroxynonenal (HNE) 是 omega-6 多不饱和脂肪酸的主要过氧化产物。HNE 与 DNA 的反应产生了四种非对映异构体 1,N(2)-γ-羟基丙酸脱氧鸟苷加合物；在动物组织中检测到这些加合物的背景水平。这四种加合物在核苷水平上的立体有择合成已经完成。此外，还开发了一种将它们定点掺入寡核苷酸的通用策略。与未加合物链相比，这些加合物是不稳定的，通过熔融温度测量。加合物 12 聚体的热失稳范围为 5 到 16 摄氏度，取决于加合物的绝对立体化学。还检查了 HNE 加合物在掺入 CpG 序列时形成链间 DNA-DNA 交联的能力。我们发现只有一种 HNE 立体异构体形成链间 DNA-DNA 交联。
• Stereocontrolled Syntheses of All Four Stereoisomeric 1,<i>N</i>²-Deoxyguanosine Adducts of the Lipid Peroxidation Product <i>trans</i>-4-Hydroxynonenal
  作者：Hao Wang、Carmelo J. Rizzo

  DOI：10.1021/ol016810c

  日期：2001.11.1

  [GRAPHICS]trans-4-Hydroxynonenal (4-HNE) is a unique product from the peroxidation of omega -6 polyunsaturated fatty acids. The major reaction of racemic 4-HNE with DNA is with deoxyguanosine to give four stereoisomeric exocyclic propano adducts. The stereospecific syntheses of these four adducts has been achieved at the nucleoside level. The synthetic approach is amenable to the synthesis of structurally defined oilgonucleotides containing these endogenous genotoxins.