2-deoxy-2-<(1-oxodecyl)amino>-D-glucopyranose | 59343-84-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-deoxy-2-<(1-oxodecyl)amino>-D-glucopyranose
• 英文别名: N-decanoylglucosamine；N-[(3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]decanamide
• CAS: 59343-84-9
• 化学式: C₁₆H₃₁NO₆
• 分子量: 333.425
• InChiKey: QIBODNRCTGRLBL-ALTVCHKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  119
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-deoxy-2-<(1-oxodecyl)amino>-D-glucopyranose 在 铂 Amberlite IR-120(H⁺) 、 氧气 、 sodium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 34.0h， 生成 2-deoxy-2-<(1-oxodecyl)amino>-α-D-glucopyranosiduronic acid methyl ester
  参考文献：
  名称：

  The structure of the glycolipid components of the aridicin antibiotic complex

  摘要：

  DOI：

  10.1021/jo00210a030
• 作为产物：
  描述：

  D-氨基葡萄糖盐酸盐 、 癸酰氯 在 碳酸氢钠 作用下， 以 1,4-二氧六环 为溶剂， 生成 2-deoxy-2-<(1-oxodecyl)amino>-D-glucopyranose
  参考文献：
  名称：

  Synthesis of some p-nitrophenyl 2-acylamino-2-deoxy-d-glucosides and their hydrolysis with the β-d-hexosaminidase from Hohenbuehelia serotina

  摘要：

  DOI：

  10.1016/s0008-6215(00)83565-x

文献信息

• The efficient synthesis of amphiphilic oximes of galactose and glucosamine
  作者：Janez Mravljak、Aleš Obreza

  DOI：10.1016/j.tetlet.2012.02.086

  日期：2012.4

  New amphiphilic oximes of galactose and glucosamine have been synthesized and characterized. The oxime functionality has been introduced to the first and sixth positions of a nonionic surfactant, consisting of a sugar polar head and a lipophilic side chain. The compounds are soluble in pyridine and sparingly soluble in other polar organic solvents and water.

  已合成并表征了半乳糖和葡糖胺的新型两亲肟。肟官能团已被引入非离子表面活性剂的第一和第六位置，该非离子表面活性剂由糖极性头和亲脂性侧链组成。该化合物可溶于吡啶，微溶于其他极性有机溶剂和水。
• New Glucosamine-Based TLR4 Agonists: Design, Synthesis, Mechanism of Action, and In Vivo Activity as Vaccine Adjuvants
  作者：Alessio Romerio、Nicole Gotri、Ana Rita Franco、Valentina Artusa、Mohammed Monsoor Shaik、Samuel T. Pasco、Unai Atxabal、Alejandra Matamoros-Recio、Marina Mínguez-Toral、Juan Diego Zalamea、Antonio Franconetti、Nicola G. A. Abrescia、Jesus Jimenez-Barbero、Juan Anguita、Sonsoles Martín-Santamaría、Francesco Peri

  DOI：10.1021/acs.jmedchem.2c01998

  日期：2023.2.23

  series). The new molecules have increased chemical stability and a shorter, more efficient, and scalable synthesis. The FP20 series showed selective activity as TLR4 agonists with a potency similar to FP18. Interestingly, despite the chemical similarity with the FP18 series, FP20 showed a different mechanism of action and immunofluorescence microscopy showed no NF-κB nor p-IRF-3 nuclear translocation but

  我们在此公开了一组小分子 TLR4 激动剂（FP20系列），其结构源自先前开发的 TLR4 配体（FP18系列）。新分子具有更高的化学稳定性和更短、更有效和可扩展的合成。FP20系列显示出作为 TLR4 激动剂的选择性活性，其效力与FP18相似。有趣的是，尽管与FP18系列具有化学相似性，但FP20显示出不同的作用机制，免疫荧光显微镜显示没有 NF-κB 或 p-IRF-3 核转位，而是 MAPK 和 NLRP3 依赖性炎性体激活。与FP20的 3D 形状相关的计算研究MD-2 口袋内具有激动剂结合特性的系列。FP20在水中的 CMC 值低于 5 μM，并且在生物活性浓度范围内观察到小单层囊泡 (SUV) 的形成。FP20在使用 OVA 抗原的小鼠疫​​苗接种实验中未显示毒性并诱导 IgG 产生，因此表明有希望的佐剂活性。
• Model for Antibiotic Optimization via Neoglycosylation:  Synthesis of Liponeoglycopeptides Active against VRE
  作者：Byron R. Griffith、Candace Krepel、Xun Fu、Sophie Blanchard、Aqeel Ahmed、Charles E. Edmiston、Jon S. Thorson

  DOI：10.1021/ja068602r

  日期：2007.7.1

  The neoglycosylation of a methoxyamine-appended vancomycin aglycon with all possible N'-decanoylglucopyranose and N'-biphenoylglucopyranose regioisomers led to the production of a focused set of liponeoglycopeptide variants in good yields and with excellent stereoselectivity. High-throughput antibacterial assays employing a unique set of vancomycin-resistant Enterococci faecalis and Enterococci faecium clinical isolates revealed that the nature and regiochemistry of glycosyl lipidation modulated vancomycin-resistent Enterococci potency. In contrast to prior work with lipoglycopeptides, this study reveals the glucose C3' or C4' as the optimal position for neoglycopeptide lipidation. This purely chemical method for the diversification of the glycolipid portion of lipoglycopeptide antibiotics is simple to perform on a large scale, requires minimal synthetic effort in sugar donor preparation, and provides access to highly active antibiotics that are not easily prepared by other state-of-the-art methods.
• Gosenca, Mirjam; Mravljak, Janez; Gasperlin, Mirjana, Acta Chimica Slovenica, 2013, vol. 60, # 2, p. 310 - 322
  作者：Gosenca, Mirjam、Mravljak, Janez、Gasperlin, Mirjana、Obreza, Ales

  DOI：——

  日期：——
• Miethchen, Ralf; Faltin, Franziska, Journal fur Praktische Chemie - Chemiker-Zeitung, 1998, vol. 340, # 6, p. 544 - 550
  作者：Miethchen, Ralf、Faltin, Franziska

  DOI：——

  日期：——