phenyl 3-O-benzoyl-6-deoxy-1-thio-β-D-mannopyranoside | 1432492-17-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 3-O-benzoyl-6-deoxy-1-thio-β-D-mannopyranoside
• 英文别名: [(2R,3R,4S,5S,6S)-3,5-dihydroxy-2-methyl-6-phenylsulfanyloxan-4-yl] benzoate
• CAS: 1432492-17-5
• 化学式: C₁₉H₂₀O₅S
• 分子量: 360.431
• InChiKey: PIQFZIUAUZQXAT-ZXBXUNHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  phenyl 3-O-benzoyl-6-deoxy-1-thio-β-D-mannopyranoside 在 吡啶 、 sodium azide 、 三氟甲磺酸酐 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 phenyl 3-O-acetyl-2,4-diazido-2,4,6-trideoxy-1-thio-β-D-galactopyranoside
  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
• 作为产物：
  描述：

  phenyl 1-thio-β-D-mannopyranoside 在 吡啶 、 lithium aluminium tetrahydride 、 二甲基二氯化锡 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 9.0h， 生成 phenyl 3-O-benzoyl-6-deoxy-1-thio-β-D-mannopyranoside
  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

• 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.