5-(mercapto)pentyl β-D-glucopyranoside | 853782-72-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 5-(mercapto)pentyl β-D-glucopyranoside
• 英文别名: (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(5-sulfanylpentoxy)oxane-3,4,5-triol
• CAS: 853782-72-6
• 化学式: C₁₁H₂₂O₆S
• 分子量: 282.358
• InChiKey: RVSGIPVVFBERPZ-KAMPLNKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  100
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  chloroauric acid 、 5-(mercapto)pentyl β-D-glucopyranoside 、 1-[2-[(2S,3S,4S,5R,6R)-4-[(2S,3S,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-6-[[(2S,3S,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,5-dihydroxyoxan-2-yl]oxyethyl]-3-[2-[2-[2-[2-(11-sulfanylundecoxy)ethoxy]ethoxy]ethoxy]ethyl]thiourea 、 1-[2-[(2S,3S,4S,5R,6R)-4-[(2R,3S,4S,5S,6R)-3-[(2R,3S,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethyl]-3-[2-[2-[2-[2-(11-sulfanylundecoxy)ethoxy]ethoxy]ethoxy]ethyl]thiourea 在 sodium tetrahydroborate 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 以1.67 mg的产率得到
  参考文献：
  名称：

  Assembling different antennas of the gp120 high mannose-type glycans on gold nanoparticles provides superior binding to the anti-HIV antibody 2G12 than the individual antennas

  摘要：

  In order to re-build Man(9)GlcNAc(2) clusters of the HIV gp120 glycoprotein, similar to 2 nm gold glyconanoparticles (GNPs) were coated with the synthetic partial structures of Man(9), the tetramannoside Man alpha 1-2Man alpha 1-2Man alpha 1- 3Man alpha 1- and the pentamannoside Man alpha 1-2Man alpha 1-3[Man alpha 1-2Man alpha 1-6]Man alpha 1-. Their interactions with the anti-HIV broadly neutralizing antibody 2G12 were studied by surface plasmon resonance (SPR)-based biosensors and saturation transfer difference (STD)-NMR spectroscopy. A synergistic effect of the tetra- and pentamannosides multimerized on a same GNP was observed. The assembly of these antennas of the gp120 high-mannose type glycan on GNPs provided superior binding to the anti-HIV antibody 2G12 with respect to GNPs carrying only the individual oligomannosides. The results presented in this work provide new molecular information on the interactions between clusters of oligomannosides and 2G12 that could help in the design of a carbohydrate-based vaccine against HIV. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.07.012
• 作为产物：
  描述：

  5-thioacetoxypentyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以65 %的产率得到5-(mercapto)pentyl β-D-glucopyranoside
  参考文献：
  名称：

  Gold nanoparticles decorated with monosaccharides and sulfated ligands as potential modulators of the lysosomal enzyme N-acetylgalactosamine-6-sulfatase (GALNS)

  摘要：

  调节 N-乙酰半乳糖胺-6-硫酸酯酶（GALNS）的活性是治疗代谢紊乱、神经性疼痛和癌症的一种很有前景的工具。为此，我们制备并检测了涂有糖和硫酸配体的金纳米粒子。

  DOI：

  10.1039/d3ob01466e

文献信息

• Gold<i>Manno</i>-Glyconanoparticles: Multivalent Systems to Block HIV-1 gp120 Binding to the Lectin DC-SIGN
  作者：Olga Martínez-Ávila、Karolin Hijazi、Marco Marradi、Caroline Clavel、Colin Campion、Charles Kelly、Soledad Penadés

  DOI：10.1002/chem.200900923

  日期：2009.9.28

  ending in thiol groups, which enable attachment of the glycoconjugates to the gold surface, have been prepared. manno‐GNPs with different spacers and variable density of mannose (oligo)saccharides have been obtained and characterized. Surface plasmon resonance (SPR) experiments with selected manno‐GNPs have been performed to study their inhibition potency towards DC‐SIGN binding to gp120. The tested manno‐GNPs

  HIV包膜糖蛋白gp120利用其表面的高甘露糖簇将树突状细胞靶向C型凝集素树突状细胞特异的细胞内粘附分子-3夺取非整联蛋白（DC‐SIGN）。模仿寡聚甘露糖苷在病毒表面的簇状存在是设计基于碳水化合物的抗病毒剂的一种策略。受gp120簇呈递的生物启发，我们设计并准备了一个小型多价水溶性金糖纳米颗粒（manno- GNP）库，其展示了高甘露糖十一碳糖Man 9 GlcNAc 2的截短的（寡聚）甘露糖苷。并测试了它们作为DC-SIGN与gp120结合的抑制剂。这些糖纳米颗粒是DC-SIGN的配体，DC-SIGN还可在感染的早期阶段通过对相关聚糖的特异性识别而与大量病原体相互作用。制备了具有以硫醇基结尾的不同间隔基的（寡）甘露糖苷，其使得糖缀合物能够附着至金表面。低聚甘露已经获得和表征具有不同间隔和甘露糖（低聚）糖的可变密度的GNP。已经进行了使用选定的甘露糖-GNP的表面等离振子共振（SPR）实
• Assembling different antennas of the gp120 high mannose-type glycans on gold nanoparticles provides superior binding to the anti-HIV antibody 2G12 than the individual antennas
  作者：Fabrizio Chiodo、Pedro M. Enríquez-Navas、Jesús Angulo、Marco Marradi、Soledad Penadés

  DOI：10.1016/j.carres.2014.07.012

  日期：2015.3

  In order to re-build Man(9)GlcNAc(2) clusters of the HIV gp120 glycoprotein, similar to 2 nm gold glyconanoparticles (GNPs) were coated with the synthetic partial structures of Man(9), the tetramannoside Man alpha 1-2Man alpha 1-2Man alpha 1- 3Man alpha 1- and the pentamannoside Man alpha 1-2Man alpha 1-3[Man alpha 1-2Man alpha 1-6]Man alpha 1-. Their interactions with the anti-HIV broadly neutralizing antibody 2G12 were studied by surface plasmon resonance (SPR)-based biosensors and saturation transfer difference (STD)-NMR spectroscopy. A synergistic effect of the tetra- and pentamannosides multimerized on a same GNP was observed. The assembly of these antennas of the gp120 high-mannose type glycan on GNPs provided superior binding to the anti-HIV antibody 2G12 with respect to GNPs carrying only the individual oligomannosides. The results presented in this work provide new molecular information on the interactions between clusters of oligomannosides and 2G12 that could help in the design of a carbohydrate-based vaccine against HIV. (C) 2014 Elsevier Ltd. All rights reserved.
• Gold nanoparticles decorated with monosaccharides and sulfated ligands as potential modulators of the lysosomal enzyme <i>N</i>-acetylgalactosamine-6-sulfatase (GALNS)
  作者：Francesca Buco、Camilla Matassini、Costanza Vanni、Francesca Clemente、Paolo Paoli、Cosimo Carozzini、Alice Beni、Francesca Cardona、Andrea Goti、Sergio Enrique Moya、Maria Grazia Ortore、Patrizia Andreozzi、Amelia Morrone、Marco Marradi

  DOI：10.1039/d3ob01466e

  日期：——

  Modulation of N-acetylgalactosamine-6-sulfatase (GALNS) activity is a promising tool for treating metabolic disorders, neuropathic pain, and cancer. Gold nanoparticles coated with sugar and sulfated ligands were prepared and assayed for this purpose.

  调节 N-乙酰半乳糖胺-6-硫酸酯酶（GALNS）的活性是治疗代谢紊乱、神经性疼痛和癌症的一种很有前景的工具。为此，我们制备并检测了涂有糖和硫酸配体的金纳米粒子。