methyl (6R)-α-D-manno-7-(cinnamido)-7-deoxyheptapyranoside

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: methyl (6R)-α-D-manno-7-(cinnamido)-7-deoxyheptapyranoside
• 英文别名: (E)-N-[(2R)-2-hydroxy-2-[(2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]ethyl]-3-phenylprop-2-enamide
• 化学式: C₁₇H₂₃NO₇
• 分子量: 353.372
• InChiKey: FHBAGZNHVWWYFA-VMPWKXKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  129
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  methyl 2,3,4-tri-O-benzyl-α-D-manno-hexodialdo-1,5-pyranoside 在 lithium aluminium tetrahydride 、 palladium 10% on activated carbon 、 氢气 、 氯化铵 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 69.17h， 生成 methyl (6R)-α-D-manno-7-(cinnamido)-7-deoxyheptapyranoside
  参考文献：
  名称：

  Synthesis of mannoheptose derivatives and their evaluation as inhibitors of the lectin LecB from the opportunistic pathogen Pseudomonas aeruginosa

  摘要：

  Biofilm formation and chronic infections with Pseudomonas aeruginosa depend on lectins produced by the bacterium. The bacterial C-type lectin LecB binds to the two monosaccharides L-fucose and D-mannose and conjugates thereof. Previously, D-mannose derivatives with amide and sulfonamide substituents at C6 were reported as potent inhibitors of the bacterial lectin LecB and LecB-mediated bacterial surface adhesion. Because D-mannose establishes a hydrogen bond via its 6-OH group with Ser23 of LecB in the crystal structure and may be beneficial for binding affinity, we extended D-mannose and synthesized mannoheptoses bearing the free 6-OH group as well as amido and sulfonamido-substituents at C7. Two series of diastereomeric mannoheptoses were synthesized and the stereochemistry was determined by X-ray crystallography. The potency of the mannoheptoses as LecB inhibitors was assessed in a competitive binding assay. The data reveal a diastereoselectivity of LecB for (6S)-mannoheptose derivatives with increased activity over methyl alpha-D-mannoside. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2015.04.010