(2S,3R,4S,5R,6R)-2-[(5,6-dihydroxy-1H-indol-3-yl)sulfanyl]-6-(hydroxymethyl)oxane-3,4,5-triol | 1192362-62-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4S,5R,6R)-2-[(5,6-dihydroxy-1H-indol-3-yl)sulfanyl]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 1192362-62-1
• 化学式: C₁₄H₁₇NO₇S
• 分子量: 343.357
• InChiKey: OCGVKSGESINKEY-YTLQFRNZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  172
• 氢给体数：
  7
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S,5R,6R)-2-[(5,6-dihydroxy-1H-indol-3-yl)sulfanyl]-6-(hydroxymethyl)oxane-3,4,5-triol 在 双氧水 、 horseradish peroxidase 作用下， 以 甲醇 为溶剂， 生成 (2S,3R,4S,5R,6R)-2-[[4-[5,6-dihydroxy-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl-1H-indol-2-yl]-5,6-dihydroxy-1H-indol-3-yl]sulfanyl]-6-(hydroxymethyl)oxane-3,4,5-triol
  参考文献：
  名称：

  Disentangling Eumelanin “Black Chromophore”: Visible Absorption Changes As Signatures of Oxidation State- and Aggregation-Dependent Dynamic Interactions in a Model Water-Soluble 5,6-Dihydroxyindole Polymer

  摘要：

  A fundamental unsettled issue concerning eumelanins, the functional biopolymers of human skin and hair, is why they are black. The experimental difficulty lies in the virtual insolubility of these pigments, causing marked scattering effects and hindering characterization of the intrinsic absorption properties of the heterogeneous species produced by oxidative polymerization of 5,6-dihydroxyindole (DHI) and related monomer precursors. The synthesis of spectrally robust, water-soluble DHI polymers is therefore an important goal in the prospects of disentangling intrinsic absorption properties of eumelanin components by circumventing scattering effects. Reported herein is the first water-soluble DHI polymer produced by oxidation of ad hoc designed 5,6-dihydroxy-3-indolyl-1-thio-beta-D-galactopyranoside (1). The dark brown polymer exhibited a distinct band at 314 nm and a broad visible absorption, resembling that of natural eumelanins. Main isolable oligomer intermediates including 2,7'- and 2,4'-biindolyls 2 and 3, attest the close resemblance to the mode of coupling of the parent DHI. Sodium borohydride reduction caused decoloration and a marked absorbance decrease in the visible region around 550 nm, but did not affect the UV band at 314 nm. Measurements of absorbance variations with dilution indicated a linear response at 314 rim, but a significant deviation from linearity in the visible region, with the largest decrease around 500 nm. It is argued that eumelanin black color is not only intrinsically defined by the overlap of pi-electron conjugated chromophores within the individual polymer components, as commonly believed, but also by oxidation state- and aggregation-dependent interchromophoric interactions causing perturbations of the heterogeneous ensemble of pi-electron systems and overall spectral broadening.

  DOI：

  10.1021/ja905162s
• 作为产物：
  描述：

  5,6-diacetoxyindol-3-yl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside 在 sodium t-butanolate 作用下， 以 甲醇 为溶剂， 反应 0.02h， 生成 (2S,3R,4S,5R,6R)-2-[(5,6-dihydroxy-1H-indol-3-yl)sulfanyl]-6-(hydroxymethyl)oxane-3,4,5-triol
  参考文献：
  名称：

  Disentangling Eumelanin “Black Chromophore”: Visible Absorption Changes As Signatures of Oxidation State- and Aggregation-Dependent Dynamic Interactions in a Model Water-Soluble 5,6-Dihydroxyindole Polymer

  摘要：

  A fundamental unsettled issue concerning eumelanins, the functional biopolymers of human skin and hair, is why they are black. The experimental difficulty lies in the virtual insolubility of these pigments, causing marked scattering effects and hindering characterization of the intrinsic absorption properties of the heterogeneous species produced by oxidative polymerization of 5,6-dihydroxyindole (DHI) and related monomer precursors. The synthesis of spectrally robust, water-soluble DHI polymers is therefore an important goal in the prospects of disentangling intrinsic absorption properties of eumelanin components by circumventing scattering effects. Reported herein is the first water-soluble DHI polymer produced by oxidation of ad hoc designed 5,6-dihydroxy-3-indolyl-1-thio-beta-D-galactopyranoside (1). The dark brown polymer exhibited a distinct band at 314 nm and a broad visible absorption, resembling that of natural eumelanins. Main isolable oligomer intermediates including 2,7'- and 2,4'-biindolyls 2 and 3, attest the close resemblance to the mode of coupling of the parent DHI. Sodium borohydride reduction caused decoloration and a marked absorbance decrease in the visible region around 550 nm, but did not affect the UV band at 314 nm. Measurements of absorbance variations with dilution indicated a linear response at 314 rim, but a significant deviation from linearity in the visible region, with the largest decrease around 500 nm. It is argued that eumelanin black color is not only intrinsically defined by the overlap of pi-electron conjugated chromophores within the individual polymer components, as commonly believed, but also by oxidation state- and aggregation-dependent interchromophoric interactions causing perturbations of the heterogeneous ensemble of pi-electron systems and overall spectral broadening.

  DOI：

  10.1021/ja905162s