methyl 2-[4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxyphenyl]acetate | 1231607-69-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-[4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxyphenyl]acetate
• 英文别名: 4-(methoxycarbonylmethyl)phenyl-α-D-mannopyranoside；methyl 2-[4-[3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxyphenyl]acetate；methyl 2-[4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]acetate
• CAS: 1231607-69-4
• 化学式: C₁₅H₂₀O₈
• 分子量: 328.319
• InChiKey: UXQUQYRYIMHFHY-IKSZGEOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 2-[4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxyphenyl]acetate 在 水 、 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 以89%的产率得到[4-(α-D-mannopyranosyloxy)phenyl]acetic acid
  参考文献：
  名称：

  Glycocluster Synthesis by Native Chemical Ligation

  摘要：

  我们制备了丝氨酸和甘露糖苷衍生的硫代酯以及一种甘露糖苷半胱氨酸衍生物，以测试原生化学连接（NCL）在无保护基团的情况下合成小型糖肽簇的方法，这种方法是糖科学领域的重要工具。通过 NCL 分别获得的糖肽和糖肽簇具有二聚化和硫醇官能团衍生化的潜力。

  DOI：

  10.1055/s-0030-1258157
• 作为产物：
  描述：

  4-(methoxycarbonylmethyl)phenyl-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以95%的产率得到methyl 2-[4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxyphenyl]acetate
  参考文献：
  名称：

  Glycocluster Synthesis by Native Chemical Ligation

  摘要：

  我们制备了丝氨酸和甘露糖苷衍生的硫代酯以及一种甘露糖苷半胱氨酸衍生物，以测试原生化学连接（NCL）在无保护基团的情况下合成小型糖肽簇的方法，这种方法是糖科学领域的重要工具。通过 NCL 分别获得的糖肽和糖肽簇具有二聚化和硫醇官能团衍生化的潜力。

  DOI：

  10.1055/s-0030-1258157

文献信息

• Structure-Based Drug Design and Optimization of Mannoside Bacterial FimH Antagonists
  作者：Zhenfu Han、Jerome S. Pinkner、Bradley Ford、Robert Obermann、William Nolan、Scott A. Wildman、Doug Hobbs、Tom Ellenberger、Corinne K. Cusumano、Scott J. Hultgren、James W. Janetka

  DOI：10.1021/jm100438s

  日期：2010.6.24

  FimH-mediated cellular adhesion to mannosylated proteins is critical in the ability of uropathogenic E. coli (UPEC) to colonize and invade the bladder epithelium during urinary tract infection. We describe the discovery and optimization of potent small-molecule FimH bacterial adhesion antagonists based on alpha-D-mannose 1-position anomeric glycosides using X-ray structure-guided drug design. Optimized biarylmannosides display low nanomolar binding affinity for FimH in a fluorescence polarization assay and submicromolar cellular activity in a hemagglutination (HA) functional cell assay of bacterial adhesion. X-ray crystallography demonstrates that the biphenyl moiety makes several key interactions with the outer surface of FimH including pi-pi interactions with Tyr-48 and an H-bonding electrostatic interaction with the Arg-98/Glu-50 salt bridge. Dimeric analogues linked through the biaryl ring show an impressive 8-fold increase in potency relative to monomeric matched pairs and represent the most potent FimH antagonists identified to date. The FimH antagonists described herein hold great potential for development as novel therapeutics for the effective treatment of urinary tract infections.
• Glycocluster Synthesis by Native Chemical Ligation
  作者：Thisbe Lindhorst、Johannes Wehner

  DOI：10.1055/s-0030-1258157

  日期：2010.9

  Serine- and mannoside-derived thioesters and a mannosidic cysteine derivative were prepared to test native chemical ligation (NCL) for protecting-group-free synthesis of small glycopeptide clusters, which are valuable tools in the glycosciences. The glycopeptides and glycopeptide clusters, respectively, which were obtained via NCL, bear the potential for dimerization and other derivatization of the thiol functionality.

  我们制备了丝氨酸和甘露糖苷衍生的硫代酯以及一种甘露糖苷半胱氨酸衍生物，以测试原生化学连接（NCL）在无保护基团的情况下合成小型糖肽簇的方法，这种方法是糖科学领域的重要工具。通过 NCL 分别获得的糖肽和糖肽簇具有二聚化和硫醇官能团衍生化的潜力。