N'-[(2S)-1-[[(2S)-1-amino-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]-N-[4-[(2R,3R,4R,5S,6R)-5-[(2R,3R,4R,5S,6R)-5-[(2R,3R,4R,5S,6R)-5-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]butanediamide | 1303982-52-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N'-[(2S)-1-[[(2S)-1-amino-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]-N-[4-[(2R,3R,4R,5S,6R)-5-[(2R,3R,4R,5S,6R)-5-[(2R,3R,4R,5S,6R)-5-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]butanediamide
• CAS: 1303982-52-6
• 化学式: C₆₂H₈₂N₆O₃₀
• 分子量: 1391.36
• InChiKey: XOMDVBMBMMJHHE-TZVCTHOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -7.9
• 重原子数：
  98
• 可旋转键数：
  27
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  578
• 氢给体数：
  22
• 氢受体数：
  30

反应信息

• 作为产物：
  描述：

  、 Fmoc-L-色氨酸 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 、 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.33h， 生成 N'-[(2S)-1-[[(2S)-1-amino-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]-N-[4-[(2R,3R,4R,5S,6R)-5-[(2R,3R,4R,5S,6R)-5-[(2R,3R,4R,5S,6R)-5-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]butanediamide
  参考文献：
  名称：

  Selective α-glucosidase substrates and inhibitors containing short aromatic peptidyl moieties

  摘要：

  We constructed a library of sugar-dipeptide conjugate to find out the best complementary against hydrophobic pocket of alpha-glucosidase. The best substrate showed 150-fold improved K-m value relative p-acetaminophenyl-alpha-D-glucopyranoside for alpha-glucosidase from Bacillus stearothermophillus. Using information from the complementary, we synthesized sp-WY and beta-Glc-sp-WY, which selectivity inhibited the cognate enzyme. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.062

文献信息

• Selective α-glucosidase substrates and inhibitors containing short aromatic peptidyl moieties
  作者：Sangeun Park、Soonsil Hyun、Jaehoon Yu

  DOI：10.1016/j.bmcl.2011.02.062

  日期：2011.4

  We constructed a library of sugar-dipeptide conjugate to find out the best complementary against hydrophobic pocket of alpha-glucosidase. The best substrate showed 150-fold improved K-m value relative p-acetaminophenyl-alpha-D-glucopyranoside for alpha-glucosidase from Bacillus stearothermophillus. Using information from the complementary, we synthesized sp-WY and beta-Glc-sp-WY, which selectivity inhibited the cognate enzyme. (C) 2011 Elsevier Ltd. All rights reserved.