N-[(2S,3R,4S,5S,6R)-2-[(2R,3S,4S,5R,6R)-6-[[(3aR,4R,5R,6S,6aS)-4-hydroxy-6-(hydroxymethyl)-2-(methylamino)-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]oxazol-5-yl]oxy]-5-amino-4-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide | 1312158-64-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[(2S,3R,4S,5S,6R)-2-[(2R,3S,4S,5R,6R)-6-[[(3aR,4R,5R,6S,6aS)-4-hydroxy-6-(hydroxymethyl)-2-(methylamino)-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]oxazol-5-yl]oxy]-5-amino-4-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 1312158-64-7
• 化学式: C₂₂H₃₈N₄O₁₃
• 分子量: 566.563
• InChiKey: BXJPJJKKAQMCRF-FLARIVPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.2
• 重原子数：
  39
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  267
• 氢给体数：
  10
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  N-[(2S,3R,4S,5S,6R)-2-[(2R,3S,4S,5R,6R)-6-[[(3aR,4R,5R,6S,6aS)-4-hydroxy-6-(hydroxymethyl)-2-(methylamino)-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]oxazol-5-yl]oxy]-5-amino-4-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide 、 sodium sulfosuccinimidyl 2-(biotinamido)ethyl-l,3-dithiopropionate 以 水 、 二甲基亚砜 为溶剂， 反应 0.5h， 以0.8 mg的产率得到N-[2-[[3-[[(2R,3R,4S,5S,6R)-2-[[(3aR,4R,5R,6S,6aS)-4-hydroxy-6-(hydroxymethyl)-2-(methylamino)-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]oxazol-5-yl]oxy]-5-[(2S,3R,4S,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)oxan-3-yl]amino]-3-oxopropyl]disulfanyl]ethyl]-5-(2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl)pentanamide
  参考文献：
  名称：

  Preparation of allosamidin and demethylallosamidin photoaffinity probes and analysis of allosamidin-binding proteins in asthmatic mice

  摘要：

  Allosamidins, metabolites of Streptomyces with strong inhibitory activities toward family 18 chitinases, show a variety of biological activities in various organisms. We prepared photoaffinity and biotinylated probes of allosamidin and demethylallosamidin, the N-demethyl derivative that shows much stronger anti-asthmatic activity than allosamidin. Mild acid hydrolysis of allosamidins afforded mono-amine derivatives, which were amidated to prepare probes with a photoactivatable aryl azide and/or biotin moieties. The derivatives with an N-acyl group at C-2 of the D-allosamine residue at the non-reducing end of allosamidins inhibited Trichoderma chitinase as strongly as the original compounds. Since the target of allosamidins in asthma is unclear, photoaffinity probes were used to analyze allosamidin-binding proteins in bronchoalveolar lavage (BAL) fluid in IL-13-induced asthmatic mice. Ym1, a chitinase-like protein, was identified as the main allosamidin-binding protein among proteins whose expression was upregulated by IL-13 in BAL fluid. Binding of allosamidins with Ym1 was confirmed by the experiments with photoaffinity probes and recombinant Ym1. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.04.012
• 作为产物：
  描述：

  demethylallosamidin 在 盐酸 、 水 作用下， 反应 10.0h， 以2.2 mg的产率得到N-[(2R,3R,4S,5S,6R)-2-[[(3aR,4R,5R,6S,6aS)-4-hydroxy-6-(hydroxymethyl)-2-(methylamino)-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]oxazol-5-yl]oxy]-5-[(2S,3R,4S,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
  参考文献：
  名称：

  Preparation of allosamidin and demethylallosamidin photoaffinity probes and analysis of allosamidin-binding proteins in asthmatic mice

  摘要：

  Allosamidins, metabolites of Streptomyces with strong inhibitory activities toward family 18 chitinases, show a variety of biological activities in various organisms. We prepared photoaffinity and biotinylated probes of allosamidin and demethylallosamidin, the N-demethyl derivative that shows much stronger anti-asthmatic activity than allosamidin. Mild acid hydrolysis of allosamidins afforded mono-amine derivatives, which were amidated to prepare probes with a photoactivatable aryl azide and/or biotin moieties. The derivatives with an N-acyl group at C-2 of the D-allosamine residue at the non-reducing end of allosamidins inhibited Trichoderma chitinase as strongly as the original compounds. Since the target of allosamidins in asthma is unclear, photoaffinity probes were used to analyze allosamidin-binding proteins in bronchoalveolar lavage (BAL) fluid in IL-13-induced asthmatic mice. Ym1, a chitinase-like protein, was identified as the main allosamidin-binding protein among proteins whose expression was upregulated by IL-13 in BAL fluid. Binding of allosamidins with Ym1 was confirmed by the experiments with photoaffinity probes and recombinant Ym1. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.04.012

文献信息

• Preparation of allosamidin and demethylallosamidin photoaffinity probes and analysis of allosamidin-binding proteins in asthmatic mice
  作者：Yosuke Sato、Shigeo Suzuki、Seiko Muraoka、Naoya Kikuchi、Naotaka Noda、Takafumi Matsumoto、Hiromasa Inoue、Hiromichi Nagasawa、Shohei Sakuda

  DOI：10.1016/j.bmc.2011.04.012

  日期：2011.5

  Allosamidins, metabolites of Streptomyces with strong inhibitory activities toward family 18 chitinases, show a variety of biological activities in various organisms. We prepared photoaffinity and biotinylated probes of allosamidin and demethylallosamidin, the N-demethyl derivative that shows much stronger anti-asthmatic activity than allosamidin. Mild acid hydrolysis of allosamidins afforded mono-amine derivatives, which were amidated to prepare probes with a photoactivatable aryl azide and/or biotin moieties. The derivatives with an N-acyl group at C-2 of the D-allosamine residue at the non-reducing end of allosamidins inhibited Trichoderma chitinase as strongly as the original compounds. Since the target of allosamidins in asthma is unclear, photoaffinity probes were used to analyze allosamidin-binding proteins in bronchoalveolar lavage (BAL) fluid in IL-13-induced asthmatic mice. Ym1, a chitinase-like protein, was identified as the main allosamidin-binding protein among proteins whose expression was upregulated by IL-13 in BAL fluid. Binding of allosamidins with Ym1 was confirmed by the experiments with photoaffinity probes and recombinant Ym1. (C) 2011 Elsevier Ltd. All rights reserved.