O-(2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl)-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-glucopyranosyl azide | 344597-16-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl)-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-glucopyranosyl azide
• CAS: 344597-16-6
• 化学式: C₄₄H₄₉N₅O₁₀
• 分子量: 807.901
• InChiKey: QODNRVSMCVDKSR-LYWYSNPMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.64
• 重原子数：
  59.0
• 可旋转键数：
  16.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  180.8
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  O-(2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl)-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-glucopyranosyl azide 在 palladium on activated charcoal 、 四(三苯基膦)钯 氢气 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N-甲基苯胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of the extracellular Ig domain I of Emmprin carrying a chitobiose unit

  摘要：

  The extracellular Ig domain I of Emmprin (34-94) carrying a chitobiose unit at Asn(44) was chemically synthesized. Boc-Asn with a benzyl-protected chitobiose unit was synthesized and used for the preparation of peptide thioester with the sequence of Emmprin (34-58) by Boc strategy. C-Terminal peptide amide (59-94) was also prepared by the solid-phase method. These segments were condensed by activation of the thioester group by silver ions to obtain a protected form of Emmprin (34-94)-NH2. After deprotection and air oxidation, the desired Emmprin (34-94)-NH2 with chitobiose was successfully obtained. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00342-2
• 作为产物：
  描述：

  2-[(2R,4aR,6S,7R,8R,8aS)-6-(tert-Butyl-diphenyl-silanyloxy)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-isoindole-1,3-dione 在 二氯二茂铪 、 二甲氨基三氟化硫 、 四丁基氟化铵 、 silver perchlorate 、 sodium hydride 、 溶剂黄146 、 乙二胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 正丁醇 为溶剂， 反应 2.0h， 生成 O-(2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl)-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-glucopyranosyl azide
  参考文献：
  名称：

  Synthesis of the extracellular Ig domain I of Emmprin carrying a chitobiose unit

  摘要：

  The extracellular Ig domain I of Emmprin (34-94) carrying a chitobiose unit at Asn(44) was chemically synthesized. Boc-Asn with a benzyl-protected chitobiose unit was synthesized and used for the preparation of peptide thioester with the sequence of Emmprin (34-58) by Boc strategy. C-Terminal peptide amide (59-94) was also prepared by the solid-phase method. These segments were condensed by activation of the thioester group by silver ions to obtain a protected form of Emmprin (34-94)-NH2. After deprotection and air oxidation, the desired Emmprin (34-94)-NH2 with chitobiose was successfully obtained. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00342-2

文献信息

• Bodipy-VAD-Fmk, a useful tool to study yeast peptide N-glycanase activity
  作者：Martin D. Witte、Carlos V. Descals、Sebastiaan V. P. de Lavoir、Bogdan I. Florea、Gijsbert A. van der Marel、Herman S. Overkleeft

  DOI：10.1039/b711531h

  日期：——

  In this paper the development of a fluorescent activity based probe, Bodipy-VAD-Fmk, for visualization of yeast peptide N-glycanase is described. The activity based probe is used to assess the efficacy of known and new chitobiose-based electrophilic traps to bind yeast peptide N-glycanase.

  本文介绍了一种基于荧光活性的探针--Bodipy-VAD-Fmk--的开发情况，该探针用于酵母多肽 N-聚糖酶的可视化。这种基于活性的探针可用于评估已知的和新的基于壳寡糖的亲电捕获剂与酵母肽 N-糖化酶结合的功效。
• Synthesis and Biological Evaluation of a Chitobiose-Based Peptide <i>N</i>-Glycanase Inhibitor Library
  作者：Martin D. Witte、Danielle Horst、Emmanuel J. H. J. Wiertz、Gijsbert A. van der Marel、Herman S. Overkleeft

  DOI：10.1021/jo801906s

  日期：2009.1.16

  Peptide N-glycanase (PNGase), the enzyme responsible for the deglycosylation of N-linked glycoproteins, has an active site related to that of cysteine proteases. Chitiobiose was equipped with electrophilic traps often used in cysteine protease inhibitors, and the resulting compounds were evaluated as PNGase inhibitors. We found that the electrophilic trap of the inhibitor has a great influence on the potency of the compounds with the chloromethyl ketone inhibitor being the first potent C-glycoside-based PNGase inhibitor.