[4-(α-D-mannopyranosyloxy)phenyl]acetic acid | 123039-18-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [4-(α-D-mannopyranosyloxy)phenyl]acetic acid
• 英文别名: 4-(carboxycarbonylmethyl)phenyl-α-D-mannopyranoside；2-[4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]acetic acid
• CAS: 123039-18-9
• 化学式: C₁₄H₁₈O₈
• 分子量: 314.292
• InChiKey: YHJWCNZGHBFVTB-CYDRSHDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  137
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [4-(α-D-mannopyranosyloxy)phenyl]acetic acid 、 S-[3-(α-D-mannopyranosyloxy)propyl]-L-cysteine ethyl ester 在 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以59%的产率得到N-{[4-(α-D-mannopyranosyloxy)phenyl]acetyl}-S-[3-(α-D-mannopyranosyloxy)propyl]-L-cysteine ethyl ester
  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：

  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

文献信息

• Cysteine-Based Mannoside Glycoclusters: Synthetic Routes and Antiadhesive Properties
  作者：Alexander Schierholt、Mirja Hartmann、Kirsten Schwekendiek、Thisbe K. Lindhorst

  DOI：10.1002/ejoc.201000185

  日期：——

  based on cysteine. By employing the orthogonally protected amino acid as scaffold molecule, a variety of structurally varied products can be obtained according to different synthetic routes. Testing of the prepared glycoclusters as inhibitors of type 1 fimbriae mediated bacterial adhesion is reported, giving hints about the influence of sugar valency, sugar scaffolding, and the nature of the glycosidic

  基于半胱氨​​酸合成了不同价态的簇状甘露糖苷。采用正交保护的氨基酸作为支架分子，可以根据不同的合成路线获得多种结构变化的产品。据报道，对制备的糖簇作为 1 型菌毛介导的细菌粘附的抑制剂进行了测试，提示了该测试系统中糖价、糖支架和糖苷苷元的性质的影响。
• Bi- and trivalent glycopeptide mannopyranosides as inhibitors of type 1 fimbriae-mediated bacterial adhesion: variation of valency, aglycon and scaffolding
  作者：Alexander Schierholt、Mirja Hartmann、Thisbe K. Lindhorst

  DOI：10.1016/j.carres.2011.04.023

  日期：2011.9

  In order to test relevant structural parameters for effective inhibition of mannose-specific bacterial adhesion, bi- and trivalent glycopeptide alpha-D-mannopyranosides were synthesized that differ in their conformational properties as well as in the spatial arrangement of attached mannosyl residues. They were tested in an inhibition adhesion assay with fluorescent Escherichia coli bacteria and testing results were referenced to the inhibitory potency of methyl alpha-D-mannopyranoside. It was shown, that besides the nature of the mannoside aglycon moiety, scaffolding of alpha-D-mannopyranosides on a peptide backbone was important for the performance of the synthesized glycopeptides as inhibitors of bacterial adhesion. (C) 2011 Elsevier Ltd. All rights reserved.
• 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。