[(2R,3S,4R,5R,6S)-5-azido-3-hydroxy-2-methyl-6-phenylsulfanyloxan-4-yl] benzoate | 1432492-18-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3S,4R,5R,6S)-5-azido-3-hydroxy-2-methyl-6-phenylsulfanyloxan-4-yl] benzoate
• CAS: 1432492-18-6
• 化学式: C₁₉H₁₉N₃O₄S
• 分子量: 385.444
• InChiKey: QYGMEGKRAYYYSV-ZIIYPAMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  95.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(2R,3S,4R,5R,6S)-5-azido-3-hydroxy-2-methyl-6-phenylsulfanyloxan-4-yl] benzoate 在 吡啶 、 sodium azide 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 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
• 作为产物：
  描述：

  phenyl 1-thio-β-D-mannopyranoside 在 吡啶 、 lithium aluminium tetrahydride 、 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 、 乙腈 为溶剂， 反应 32.0h， 生成 [(2R,3S,4R,5R,6S)-5-azido-3-hydroxy-2-methyl-6-phenylsulfanyloxan-4-yl] benzoate
  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

• Total Synthesis of the All-Rare Sugar-Containing Pentasaccharide Repeating Unit of the O-Polysaccharide of <i>Plesiomonas shigelloides</i> Strain 302-73 (Serotype O1)
  作者：Sayantan Biswas、Balasaheb K. Ghotekar、Suvarn S. Kulkarni

  DOI：10.1021/acs.orglett.1c02239

  日期：2021.8.6

  First total synthesis of the conjugation-ready pentasaccharide repeating unit of Plesiomonas shigelloides strain 302-73 (serotype O1) is reported. The complex target pentasaccharide is composed of all-rare amino sugars such as orthogonally functionalized d-bacillosamine, l-fucosamine, and l-pneumosamine linked through four consecutive α-linkages. The poor nucleophilicity of axial 4-OH of l-fucosamine

  首次报道了志贺单胞菌菌株 302-73（血清型 O1）的共轭五糖重复单元的全合成。复杂的目标五糖由所有稀有氨基糖组成，例如正交功能化的d-杆菌胺、l-岩藻糖胺和l - pneumosamine，通过四个连续的 α-键连接。l-岩藻糖胺的轴向 4-OH 亲核性差和立体选择性糖基化是全合成中的关键挑战，全合成通过最长的 27 步线性序列完成，总产率为 3%。
• 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.