phenyl 3-O-acetyl-6-deoxy-1-thio-β-D-mannopyranoside | 1432492-20-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 3-O-acetyl-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] acetate
• CAS: 1432492-20-0
• 化学式: C₁₄H₁₈O₅S
• 分子量: 298.36
• InChiKey: LKNNTNJZIMNTNT-HAAGFXOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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-acetyl-6-deoxy-1-thio-β-D-mannopyranoside 在 吡啶 、 N-碘代丁二酰亚胺 、 sodium azide 、 三氟甲磺酸 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成
  参考文献：
  名称：

  细菌聚糖生物合成的代谢抑制剂

  摘要：

  细菌细胞壁是典型的药物靶标，因为它在宿主定植、病原体存活和免疫逃避中起着关键作用。致密的细胞壁糖萼含有人类细胞中不存在的独特单糖，将单糖正确组装成高级聚糖对于细菌适应性和发病机制至关重要。然而，细菌糖基化酶的系统研究和抑制仍然具有挑战性。细菌产生的聚糖含有稀有的脱氧氨基糖，传统的聚糖分析难以处理，这使得细菌聚糖的研究和糖基化抑制剂的产生变得复杂。为了在缺乏详细结构或酶信息的情况下简化细菌聚糖功能的研究，我们基于稀有细菌单糖支架制作了代谢抑制剂。评估了代谢抑制剂干扰致病菌和共生细菌物种的聚糖生物合成和适应性的能力。三种代谢抑制剂导致显着的结构和功能缺陷幽门螺杆菌。引人注目的是，这些抑制剂以细菌选择性方式起作用。这些代谢抑制剂将为细菌糖基化酶的系统研究提供一个平台，目前现有工具无法做到这一点。此外，它们的选择性将为开发治疗传染病的新型窄谱抗生素提供途径。我们的抑制方法是通用的，将加快在一系列系

  DOI：

  10.1039/c9sc05955e
• 作为产物：
  描述：

  phenyl 6-O-tosyloxy-1-thio-β-D-mannopyranoside 在 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 3.0h， 生成 phenyl 3-O-acetyl-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

• Total synthesis of the bacillosamine containing α-l-serine linked trisaccharide of Neisseria meningitidis
  作者：Madhu Emmadi、Suvarn S. Kulkarni

  DOI：10.1016/j.carres.2014.04.011

  日期：2014.11

  Total synthesis of the bacillosamine containing L-serine linked O-trisaccharide of Neisseria meningitidis is described. The synthesis entails installation of two consecutive alpha-linkages including the coupling of bacillosamine with L-serine derivative. (C) 2014 Elsevier Ltd. All rights reserved.
• 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.
• Polysaccharide corona: The acetyl-rich envelope wraps the extracellular membrane vesicles and the cells of Shewanella vesiculosa providing adhesiveness
  作者：Angela Casillo、Rossella Di Guida、Domenico Cavasso、Antonietta Stellavato、Diksha Rai、Fumiaki Yokoyama、Kouhei Kamasaka、Jun Kawamoto、Tatsuo Kurihara、Chiara Schiraldi、Suvarn Kulkarni、Luigi Paduano、Maria Michela Corsaro

  DOI：10.1016/j.carbpol.2022.120036

  日期：2022.12