p-methylphenyl 2,4,6-tri-O-acetyl-3-azido-3-deoxy-1-thio-β-D-glucopyranoside | 868618-88-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methylphenyl 2,4,6-tri-O-acetyl-3-azido-3-deoxy-1-thio-β-D-glucopyranoside
• 英文别名: p-tolyl 2,4,6-tri-O-acetyl-3-azido-3-deoxy-1-thio-β-D-glucopyranoside
• CAS: 868618-88-6
• 化学式: C₁₉H₂₃N₃O₇S
• 分子量: 437.474
• InChiKey: WDAIMPBZEFJQCT-ZRSRNVLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.92
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  136.89
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  p-methylphenyl 2,4,6-tri-O-acetyl-3-azido-3-deoxy-1-thio-β-D-glucopyranoside 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 三氟甲磺酸三甲基硅酯 、 水 、 氢气 、 sodium methylate 、 sodium carbonate 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， -20.0~20.0 ℃ 、101.33 kPa 条件下， 反应 89.34h， 生成
  参考文献：
  名称：

  An efficient method to synthesize novel 5-O-(6′-modified)-mycaminose 14-membered ketolides

  摘要：

  A new and facile procedure was developed to synthesize novel 5-O-(6'-modified)-mycaminose 14-membered ketolides by adopting different protective strategies and comparing various glycosylation conditions. Seven trichloroacetimidate donors which had different types of substituent groups at C-6 position were synthesized to couple with the erythronolide. Nine novel 5-O-(6'-modified)-mycaminose 14 -membered ketolides were obtained to verify the utility of the method. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.11.029
• 作为产物：
  描述：

  3-azido-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 在 盐酸 、 三氟化硼乙醚 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 p-methylphenyl 2,4,6-tri-O-acetyl-3-azido-3-deoxy-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Branched aminoglycosides: Biochemical studies and antibacterial activity of neomycin B derivatives

  摘要：

  The C5"-OH group in neomycin B was glycosylated with a variety of mono- and di-saccharides to probe the effect of introduction of additional binding elements on antibacterial activity and interaction with the aminoglycosides modifying enzyme APH(3')-IIIa. The designed structures show antibacterial activity superior to that of neomycin B against pathogenic and resistant strains, while in parallel they demonstrate poor substrate activity with APH(3')IIIa. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.05.058

文献信息

• Chemical Synthesis and Immunological Evaluation of a Pentasaccharide Bearing Multiple Rare Sugars as a Potential Anti‐pertussis Vaccine
  作者：Peng Wang、Chang‐xin Huo、Shuyao Lang、Kyle Caution、Setare Tahmasebi Nick、Purnima Dubey、Rajendar Deora、Xuefei Huang

  DOI：10.1002/anie.201915913

  日期：2020.4.16

  With the infection rate of Bordetella pertussis at a 60‐year high, there is an urgent need for new anti‐pertussis vaccines. The lipopolysaccharide (LPS) of B. pertussis is an attractive antigen for vaccine development. With the presence of multiple rare sugars and unusual glycosyl linkages, the B. pertussis LPS is a highly challenging synthetic target. In this work, aided by molecular dynamics simulation

  随着百日咳博德特氏菌的感染率达到60年来的最高水平，迫切需要新的抗百日咳疫苗。百日咳博德特氏菌的脂多糖（LPS）是用于疫苗开发的有吸引力的抗原。由于存在多种稀有糖和异常的糖基键，百日咳博德特氏菌LPS是一个极富挑战性的合成目标。在这项工作中，借助于分子动力学模拟和建模，首次化学合成了百日咳-LPS-样五糖。将五糖与作为疫苗候选物的强力载体噬菌体Qβ缀合。用缀合物诱导的强大抗抗IgG IgG免疫小鼠，IgG效价达到数百万个酶联免疫吸附测定（ELISA）单位。产生的抗体持久且可加强，可识别百日咳博德特氏菌的多种临床菌株，突出了Qβ-聚糖作为新型抗百日咳疫苗的潜力。