N-((1S,2R)-2-(3-pyridinecarboxamido)cyclohexanecarboxyl)-α-L-fucopyranosylamine | 1242140-23-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-((1S,2R)-2-(3-pyridinecarboxamido)cyclohexanecarboxyl)-α-L-fucopyranosylamine
• 英文别名: N-[(1S,2R)-2-(3-pyridinecarboxamido)cyclohexanecarboxy]-α-L-fucopyranosylamine；N-[(1R,2S)-2-[[(2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]carbamoyl]cyclohexyl]pyridine-3-carboxamide
• CAS: 1242140-23-3
• 化学式: C₁₉H₂₇N₃O₆
• 分子量: 393.44
• InChiKey: FYLKMMARGWJEMH-YPUPQTIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  141
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  N-((1S,2R)-2-(3-pyridinecarboxamido)cyclohexanecarboxyl)-2,3,4-tri-O-acetyl-α-L-fucopyranosylamine 在 甲醇 、 sodium methylate 作用下， 以95%的产率得到N-((1S,2R)-2-(3-pyridinecarboxamido)cyclohexanecarboxyl)-α-L-fucopyranosylamine
  参考文献：
  名称：

  Second generation of fucose-based DC-SIGN ligands : affinity improvement and specificity versus Langerin

  摘要：

  DC-SIGN和Langerin是两种C型凝集素，它们参与HIV感染的初始步骤：前者作为病毒附着因子，促进病毒侵入免疫系统，后者具有保护作用。针对DC-SIGN的潜在抗病毒化合物采用共同的岩藻糖基酰胺锚合成。通过表面等离子体共振（SPR）测试它们的DC-SIGN亲和力，发现其与天然配体Lewis-X（LeX）相似。这些化合物还被发现对DC-SIGN具有选择性，并且与Langerin仅弱相互作用。这些分子可能成为治疗性传播HIV感染的有用工具。

  DOI：

  10.1039/c1ob05573a

文献信息

• Monovalent and bivalent N-fucosyl amides as high affinity ligands for Pseudomonas aeruginosa PA-IIL lectin
  作者：Manuel Andreini、Marko Anderluh、Aymeric Audfray、Anna Bernardi、Anne Imberty

  DOI：10.1016/j.carres.2010.03.012

  日期：2010.7

  natural target. Four monovalent and one divalent alpha-fucosyl amides have been tested for their affinity for a fucose-binding lectin from Pseudomonas aeruginosa. Isothermal calorimetric titrations demonstrated that they bind to the lectin in the micromolar range, with highest affinity for the divalent ligand. Molecular modelling established that, compared to Omicron-fucoside compounds, the glycomimetic

  细菌与人糖缀合物的粘附可被与天然靶标竞争的可溶性糖模拟物抑制。已经测试了四种单价和一种二价的α-岩藻糖酰胺与铜绿假单胞菌的岩藻糖结合凝集素的亲和力。等温滴定表明，它们在微摩尔范围内与凝集素结合，对二价配体具有最高的亲和力。分子建模证实，与Omicron-岩藻糖苷化合物相比，拟糖酰胺基团导致水桥氢键的丧失，而糖苷配基与蛋白质表面的额外接触可以部分补偿。
• Second generation of fucose-based DC-SIGN ligands : affinity improvement and specificity versus Langerin
  作者：Manuel Andreini、Daniela Doknic、Ieva Sutkeviciute、José J. Reina、Janxin Duan、Eric Chabrol、Michel Thepaut、Elisabetta Moroni、Fabio Doro、Laura Belvisi、Joerg Weiser、Javier Rojo、Franck Fieschi、Anna Bernardi

  DOI：10.1039/c1ob05573a

  日期：——

  DC-SIGN and Langerin are two C-type lectins involved in the initial steps of HIV infections: the former acts as a viral attachment factor and facilitates viral invasion of the immune system, the latter has a protective effect. Potential antiviral compounds targeted against DC-SIGN were synthesized using a common fucosylamide anchor. Their DC-SIGN affinity was tested by SPR and found to be similar to that of the natural ligand Lewis-X (LeX). The compounds were also found to be selective for DC-SIGN and to interact only weakly with Langerin. These molecules are potentially useful therapeutic tools against sexually transmitted HIV infection.

  DC-SIGN和Langerin是两种C型凝集素，它们参与HIV感染的初始步骤：前者作为病毒附着因子，促进病毒侵入免疫系统，后者具有保护作用。针对DC-SIGN的潜在抗病毒化合物采用共同的岩藻糖基酰胺锚合成。通过表面等离子体共振（SPR）测试它们的DC-SIGN亲和力，发现其与天然配体Lewis-X（LeX）相似。这些化合物还被发现对DC-SIGN具有选择性，并且与Langerin仅弱相互作用。这些分子可能成为治疗性传播HIV感染的有用工具。