phenyl 2,4-diazido-3-O-benzoyl-2,4,6-trideoxy-1-thio-β-D-glucopyranoside | 1432492-25-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: phenyl 2,4-diazido-3-O-benzoyl-2,4,6-trideoxy-1-thio-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6S)-3,5-diazido-2-methyl-6-phenylsulfanyloxan-4-yl] benzoate
• CAS: 1432492-25-5
• 化学式: C₁₉H₁₈N₆O₃S
• 分子量: 410.456
• InChiKey: YQPQILICVLTGJG-FZWVUDROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  89.6
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  phenyl 2,4-diazido-3-O-benzoyl-2,4,6-trideoxy-1-thio-β-D-glucopyranoside 在 palladium on activated charcoal 、 氢气 、 碳酸氢钠 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 10.0h， 生成
  参考文献：
  名称：

  Development of Rare Bacterial Monosaccharide Analogs for Metabolic Glycan Labeling in Pathogenic Bacteria

  摘要：

  Bacterial glycans contain rare, exclusively bacterial monosaccharides that are frequently linked to pathogenesis and essentially absent from human cells. Therefore, bacterial glycans are intriguing molecular targets. However, systematic discovery of bacterial glycoproteins is hampered by the presence of rare deoxy amino sugars, which are refractory to traditional glycan-binding reagents. Thus, the development of chemical tools that label bacterial glycans is a crucial step toward discovering and targeting these biomolecules. Here, we explore the extent to which metabolic glycan labeling facilitates the studying and targeting of glycoproteins in a range of pathogenic and symbiotic bacterial strains. We began with an azide-containing analog of the naturally abundant monosaccharide N-acetylglucosamine and discovered that it is not broadly incorporated into bacterial glycans, thus revealing a need for additional azidosugar substrates to broaden the utility of metabolic glycan labeling in bacteria. Therefore, we designed and synthesized analogs of the rare deoxy amino 7-sugars N-acetylfucosamine, bacillosamine, and 2,4-diacetamido-2,4,6-trideoxygalactose and established that these analogs are differentially incorporated into glycan-containing structures in a range of pathogenic and symbiotic bacterial species. Further application of these analogs will refine our knowledge of the glycan repertoire in diverse bacteria and may find utility in treating a variety of infectious diseases with selectivity.

  DOI：

  10.1021/acschembio.6b00790
• 作为产物：
  描述：

  phenyl 1-thio-β-D-mannopyranoside 在 吡啶 、 lithium aluminium tetrahydride 、 sodium azide 、 三氟甲磺酸酐 、 tetrabutylammonium azide 、 二甲基二氯化锡 、 N,N-二异丙基乙胺 、 四丁基亚硝酸铵 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 42.0h， 生成 phenyl 2,4-diazido-3-O-benzoyl-2,4,6-trideoxy-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  迅速合成细菌，稀有的糖结构单元以获取原核糖苷†

  摘要：

  细菌具有异常的聚糖，无法通过分离获得。在这里，我们描述了一种通用的和不同的策略，用于从以下分子合成稀有的细菌脱氧氨基己吡喃糖苷结构单元D-甘露糖。该方法适用于脑膜炎奈瑟球菌L-丝氨酸连接的三糖的首次全合成。

  DOI：

  10.1039/c3ob40615f

文献信息

• Synthesis of Rare Deoxy Amino Sugar Building Blocks Enabled the Total Synthesis of a Polysaccharide Repeating Unit Analogue from the LPS of <i>Psychrobacter cryohalolentis</i> K5^T
  作者：Madhu Emmadi、Suvarn S. Kulkarni

  DOI：10.1021/acs.joc.8b02037

  日期：2018.12.7

  K5T strain was reported. Due to the presence of unnatural amino sugars and branched linkages, its structure is unique. Herein we report the total synthesis of an LPS analogue of P. cryohalolentis K5T. After overcoming the issues like ring conformation changes and elimination of triflate, we were able to develop a strategy for the synthesis of the newly reported 2,3,4-triacetamido-2,3,4-trideoxy-l-arabinose

  脂多糖（LPS）在体液免疫中起关键作用。最近，对LPS的结构嗜冷cryohalolentis K5 Ť菌株的报道。由于存在非天然氨基糖和支链，其结构是独特的。在此，我们报告了P的LPS类似物的总合成。cryohalolentis K5牛逼。克服像环的构象变化和消除三氟甲磺酸的问题之后，我们能够制定一项战略，在新报告的2,3,4- triacetamido -2,3,4-三脱氧合成升-阿拉伯糖衍生物。从非还原端到还原端，不同的供体与合适的受体偶联，并且进一步的官能团修饰递送了受保护的LPS六糖重复单元。官能团修饰后，我们无法氧化受阻伯羟基以合成目标分子。或者，除去永久性保护基团，得到了Psychobacter cryohalolentis K5 T的LPS六糖重复单元类似物。
• Expeditious synthesis of bacterial, rare sugar building blocks to access the prokaryotic glycome
  作者：Madhu Emmadi、Suvarn S. Kulkarni

  DOI：10.1039/c3ob40615f

  日期：——

  Bacteria have unusual glycans which are not accessible by isolation. Herein, we describe a general and divergent strategy for the synthesis of the rare, bacterial deoxy amino hexopyranoside building blocks from D-mannose. The methodology is applied to the first total synthesis of the L-serine linked trisaccharide of Neisseria meningitidis.

  细菌具有异常的聚糖，无法通过分离获得。在这里，我们描述了一种通用的和不同的策略，用于从以下分子合成稀有的细菌脱氧氨基己吡喃糖苷结构单元D-甘露糖。该方法适用于脑膜炎奈瑟球菌L-丝氨酸连接的三糖的首次全合成。
• Development of Rare Bacterial Monosaccharide Analogs for Metabolic Glycan Labeling in Pathogenic Bacteria
  作者：Emily L. Clark、Madhu Emmadi、Katharine L. Krupp、Ananda R. Podilapu、Jennifer D. Helble、Suvarn S. Kulkarni、Danielle H. Dube

  DOI：10.1021/acschembio.6b00790

  日期：2016.12.16

  Bacterial glycans contain rare, exclusively bacterial monosaccharides that are frequently linked to pathogenesis and essentially absent from human cells. Therefore, bacterial glycans are intriguing molecular targets. However, systematic discovery of bacterial glycoproteins is hampered by the presence of rare deoxy amino sugars, which are refractory to traditional glycan-binding reagents. Thus, the development of chemical tools that label bacterial glycans is a crucial step toward discovering and targeting these biomolecules. Here, we explore the extent to which metabolic glycan labeling facilitates the studying and targeting of glycoproteins in a range of pathogenic and symbiotic bacterial strains. We began with an azide-containing analog of the naturally abundant monosaccharide N-acetylglucosamine and discovered that it is not broadly incorporated into bacterial glycans, thus revealing a need for additional azidosugar substrates to broaden the utility of metabolic glycan labeling in bacteria. Therefore, we designed and synthesized analogs of the rare deoxy amino 7-sugars N-acetylfucosamine, bacillosamine, and 2,4-diacetamido-2,4,6-trideoxygalactose and established that these analogs are differentially incorporated into glycan-containing structures in a range of pathogenic and symbiotic bacterial species. Further application of these analogs will refine our knowledge of the glycan repertoire in diverse bacteria and may find utility in treating a variety of infectious diseases with selectivity.