N-(hexadecanoyl)-4-O-(α-D-glucopyranosyl)-β-D-glucopyranosyl-amine | 1178586-59-8

• 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: N-(hexadecanoyl)-4-O-(α-D-glucopyranosyl)-β-D-glucopyranosyl-amine
• 英文别名: Mal-β-NH-COC15
• CAS: 1178586-59-8
• 化学式: C₂₈H₅₃NO₁₁
• 分子量: 579.729
• InChiKey: URIJGEBRKWZFTG-CWBGAEIDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.21
• 重原子数：
  40.0
• 可旋转键数：
  19.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  198.4
• 氢给体数：
  8.0
• 氢受体数：
  11.0

反应信息

• 作为产物：
  描述：

  (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(((2R,3R,4S,5R,6R)-4,5-diacetoxy-2-(acetoxymethyl)-6-palmitamidotetrahydro-2H-pyran-3-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以98%的产率得到N-(hexadecanoyl)-4-O-(α-D-glucopyranosyl)-β-D-glucopyranosyl-amine
  参考文献：
  名称：

  麦芽糖基两亲物作为超分子水凝胶剂的合成与表征

  摘要：

  通过酰胺化或铜（I）催化的叠氮化物-炔烃[3 + 2]环加成反应连接麦芽糖的极性头和疏水性的线性链，从而制备了低分子量的两亲性糖脂。这些两亲材料的液晶性质已经被表征。还研究了这些糖脂的化学结构对水中胶凝特性的影响。通过两种组分的点击偶联获得的糖脂在室温下产生稳定的水凝胶。通过这些胶凝剂的自组装获得的超分子水凝胶的原纤维结构已经通过电子显微镜表征。纤维显示出一定的扭曲，这可能与两亲性的手性超分子排列有关，如圆二色性（CD）所证实。

  DOI：

  10.1021/la203447e

文献信息

• Phase diagrams of monoacylated amide-linked disaccharide glycolipids
  作者：S. Gerber、M. Wulf、G. Milkereit、V. Vill、J. Howe、M. Roessle、P. Garidel、T. Gutsmann、K. Brandenburg

  DOI：10.1016/j.chemphyslip.2009.01.003

  日期：2009.4

  A series of monoacylated glycolipids with even-numbered acyl chain lengths ranging from saturated C11 to 05 and an unsaturated C17:1 fatty acid connected by an amide in linkage to the disaccharide head groups maltose, melibiose and lactose were synthesized. The structural polymorphism of the glycolipids was investigated using Fourier-transform infrared spectroscopy and differential scanning calorimetry, for the detection of the gel to liquid-crystalline acyl chain melting behaviour and small-angle X-ray scattering for the elucidation of the physical structure of the lipid aggregates. Also, the phase morphology was studied by polarizing microscopy in contact preparations. The data clearly show the existence of uni- and multilamellar structures. Although only one acyl chain is present, there is no evidence for the existence of micelles - of spherical or of cylindrical (HI) type - or of interdigitated phases. The preference for lamellar phases seems to be correlated with the intrinsic high conformational order of the amide linkage of these compounds which inhibits the formation of highly curved structures. (c) 2009 Elsevier Ireland Ltd. All rights reserved.