tert-butyldimethylsilyl 4-O-(benzyloxycarbonyl)-2-deoxy-3-O-hexanoyl-2-(hexanoylamino)-β-D-glucopyranoside | 506441-97-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyldimethylsilyl 4-O-(benzyloxycarbonyl)-2-deoxy-3-O-hexanoyl-2-(hexanoylamino)-β-D-glucopyranoside
• 英文别名: [(2S,3R,4R,5S,6R)-2-[tert-butyl(dimethyl)silyl]oxy-3-(hexanoylamino)-6-(hydroxymethyl)-5-phenylmethoxycarbonyloxyoxan-4-yl] hexanoate
• CAS: 506441-97-0
• 化学式: C₃₂H₅₃NO₉Si
• 分子量: 623.86
• InChiKey: PYUYXOQJJRPXCT-CXXSABEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.0
• 重原子数：
  43
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  130
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  tert-butyldimethylsilyl 4-O-(benzyloxycarbonyl)-2-deoxy-3-O-hexanoyl-2-(hexanoylamino)-β-D-glucopyranoside 在 吡啶 、 三氟甲磺酸三甲基硅酯 、 MS 4 Angstroem 、 氢氟酸 、 溶剂黄146 、 镉 、 锌 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 12.0h， 生成 4-O-(benzyloxycarbonyl)-6-O-[6-O-(benzyloxycarbonyl)-4-O-[bis(benzyloxy)phosphoryl]-2-deoxy-3-O-hexanoyl-2-(hexanoylamino)-β-D-glucopyranosyl]-2-deoxy-3-O-hexanoyl-2-(hexanoylamino)-D-glucopyranose
  参考文献：
  名称：

  Synthesis of Lipid A Derivatives and Their Interactions with Polymyxin B and Polymyxin B Nonapeptide

  摘要：

  Lipid A is the causative agent of Gram-negative sepsis, a leading cause of mortality among hospitalized patients. Compounds that bind lipid A can limit its detrimental effects. Polymyxin B, a cationic peptide antibiotic, is one of the simplest molecules capable of selectively binding lipid A and may serve as a model for further development of lipid A binding agents. However, association of polymyxin B with lipid A is not fully understood, primarily due to the low solubility of lipid A in water and inhomogeneity of lipid A preparations. To better understand lipid A-polymyxin B interaction, pure lipid A derivatives were prepared with incrementally varied lipid chain lengths. These compounds proved to be more soluble in water than lipid A, with higher aggregation concentrations. Isothermal titration calorimetric studies of these lipid A derivatives with polymyxin B and polymyxin B nonapeptide indicate that binding stoichiometries (peptide to lipid A derivative) are less than 1 and that affinities of these binding partners correlate with the aggregation states of the lipid A derivatives. These studies also suggest that cooperative ionic interactions dominate association of polymyxin B and polymyxin B nonapeptide with lipid A.

  DOI：

  10.1021/ja0284456
• 作为产物：
  描述：

  N-hexanoyl glucosamine 在 吡啶 、 咪唑 、 甲醇 、 4-二甲氨基吡啶 、 氢氟酸 、 氨 、 4-甲基苯磺酸吡啶 、 溶剂黄146 、 乙二胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 55.5h， 生成 tert-butyldimethylsilyl 4-O-(benzyloxycarbonyl)-2-deoxy-3-O-hexanoyl-2-(hexanoylamino)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Lipid A Derivatives and Their Interactions with Polymyxin B and Polymyxin B Nonapeptide

  摘要：

  Lipid A is the causative agent of Gram-negative sepsis, a leading cause of mortality among hospitalized patients. Compounds that bind lipid A can limit its detrimental effects. Polymyxin B, a cationic peptide antibiotic, is one of the simplest molecules capable of selectively binding lipid A and may serve as a model for further development of lipid A binding agents. However, association of polymyxin B with lipid A is not fully understood, primarily due to the low solubility of lipid A in water and inhomogeneity of lipid A preparations. To better understand lipid A-polymyxin B interaction, pure lipid A derivatives were prepared with incrementally varied lipid chain lengths. These compounds proved to be more soluble in water than lipid A, with higher aggregation concentrations. Isothermal titration calorimetric studies of these lipid A derivatives with polymyxin B and polymyxin B nonapeptide indicate that binding stoichiometries (peptide to lipid A derivative) are less than 1 and that affinities of these binding partners correlate with the aggregation states of the lipid A derivatives. These studies also suggest that cooperative ionic interactions dominate association of polymyxin B and polymyxin B nonapeptide with lipid A.

  DOI：

  10.1021/ja0284456

文献信息

• Synthesis of Lipid A Derivatives and Their Interactions with Polymyxin B and Polymyxin B Nonapeptide
  作者：Ning Yin、Ryan L. Marshall、Sannali Matheson、Paul B. Savage

  DOI：10.1021/ja0284456

  日期：2003.3.1

  Lipid A is the causative agent of Gram-negative sepsis, a leading cause of mortality among hospitalized patients. Compounds that bind lipid A can limit its detrimental effects. Polymyxin B, a cationic peptide antibiotic, is one of the simplest molecules capable of selectively binding lipid A and may serve as a model for further development of lipid A binding agents. However, association of polymyxin B with lipid A is not fully understood, primarily due to the low solubility of lipid A in water and inhomogeneity of lipid A preparations. To better understand lipid A-polymyxin B interaction, pure lipid A derivatives were prepared with incrementally varied lipid chain lengths. These compounds proved to be more soluble in water than lipid A, with higher aggregation concentrations. Isothermal titration calorimetric studies of these lipid A derivatives with polymyxin B and polymyxin B nonapeptide indicate that binding stoichiometries (peptide to lipid A derivative) are less than 1 and that affinities of these binding partners correlate with the aggregation states of the lipid A derivatives. These studies also suggest that cooperative ionic interactions dominate association of polymyxin B and polymyxin B nonapeptide with lipid A.