demethylallosamidin | 124796-31-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: demethylallosamidin
• 英文别名: Demethylallosamidin；N-[(2S,3R,4S,5S,6R)-2-[(2R,3S,4S,5R,6R)-6-[[(3aR,4R,5R,6S,6aS)-4-hydroxy-6-(hydroxymethyl)-2-methylimino-3,3a,4,5,6,6a-hexahydrocyclopenta[d][1,3]oxazol-5-yl]oxy]-5-acetamido-4-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 124796-31-2
• 化学式: C₂₄H₄₀N₄O₁₄
• 分子量: 608.6
• InChiKey: NYHHTEVXEUTBMH-AJPXZRRQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.9
• 重原子数：
  42
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  270
• 氢给体数：
  10
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  demethylallosamidin 在 盐酸 、 水 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 10.5h， 生成 N-[2-[[3-[[(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-acetamido-4-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-4,5-dihydroxy-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：

  (1S,2S,3R,4R,5S)-2-Amino-3-benzyloxy-5-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-cyclopentanol 在 palladium on activated charcoal 盐酸 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 氢气 、 mercury(II) oxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 58.5h， 生成 demethylallosamidin
  参考文献：
  名称：

  Synthesis of demethylallosamidin, a yeast chitinase inhibitor; use of disaccharide glycosyl donor carrying novel neighboring group

  摘要：

  In the synthesis of novel pseudotrisaccharide called demethylallosamidin, a thioglycoside carrying the 2-acetamido group served as an efficient glycosyl donor through undergoing specific N,O-isopropylidenation at the 2- and 3-positions which prohibits oxazoline ring formation during the glycosidation reaction.

  DOI：

  10.1016/s0040-4039(00)73136-4

文献信息

• Kinoshita, Masayoshi; Sakuda, Shohei; Yamada, Yasuhiro, Bioscience, Biotechnology and Biochemistry, 1993, vol. 57, # 10, p. 1699 - 1703
  作者：Kinoshita, Masayoshi、Sakuda, Shohei、Yamada, Yasuhiro

  DOI：——

  日期：——
• Synthesis of demethylallosamidin, a yeast chitinase inhibitor; use of disaccharide glycosyl donor carrying novel neighboring group
  作者：Shunya Takahashi、Hiroyuki Terayama、Hiroyoshi Kuzuhara

  DOI：10.1016/s0040-4039(00)73136-4

  日期：1994.6

  In the synthesis of novel pseudotrisaccharide called demethylallosamidin, a thioglycoside carrying the 2-acetamido group served as an efficient glycosyl donor through undergoing specific N,O-isopropylidenation at the 2- and 3-positions which prohibits oxazoline ring formation during the glycosidation reaction.
• 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.