10-azidodecyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside | 574737-32-9

• 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: 10-azidodecyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside
• CAS: 574737-32-9
• 化学式: C₂₄H₃₉N₃O₁₀
• 分子量: 529.588
• InChiKey: FOWRQBOMMLANNX-OYTPZHDJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.52
• 重原子数：
  37.0
• 可旋转键数：
  17.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  172.42
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  10-azidodecyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 10-azidodecyl β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of polyanionic glycopolymers for the facile assembly of glycosyl arrays

  摘要：

  Polyanionic glycopolymers were synthesized aiming at establishing a simple process for assembling glycosyl arrays. The synthetic glycopolymers carry the key carbohydrate epitopes of alpha-D-galactobioside (Gb(2)), beta-lactoside, and U-D-mannopyranoside, each of which serves as a ligand of bacterial toxins and adhesion proteins. The Gb(2) epitope, prepared from penta-O-acetyl-D-galactopyranose, was coupled with poly(ethylene-alt-maleic anhydride) in a polymer reaction to afford a Gb(2)-embedded glycopolymer having also carboxylate (COO-) polyanions at the side chain. The polyanionic glycopolymer was then applied to a preparation of sugar-coated gold electrodes, which involves an alternating layer-by-layer adsorption based on electrostatic interactions. The presence of the Gb(2)-Coat on the surface was evidenced by Fourier transform infrared reflection absorption spectroscopy. The Gb(2)-coated glyco-chip was stable in 10 mM HEPES buffer containing 150 mM NaCl aq. Other glycopolymers carrying the beta-lactoside and alpha-D-mannopyranoside epitopes were applied to the same assembling process. The derived glycosyl arrays will be useful for detecting Shiga toxins, other pathogenic toxins and viruses when applied as glyco-chips for surface plasmon resonance or quartz crystal microbalance technique. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.03.102
• 作为产物：
  描述：

  10-bromodecyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以99%的产率得到10-azidodecyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of polyanionic glycopolymers for the facile assembly of glycosyl arrays

  摘要：

  Polyanionic glycopolymers were synthesized aiming at establishing a simple process for assembling glycosyl arrays. The synthetic glycopolymers carry the key carbohydrate epitopes of alpha-D-galactobioside (Gb(2)), beta-lactoside, and U-D-mannopyranoside, each of which serves as a ligand of bacterial toxins and adhesion proteins. The Gb(2) epitope, prepared from penta-O-acetyl-D-galactopyranose, was coupled with poly(ethylene-alt-maleic anhydride) in a polymer reaction to afford a Gb(2)-embedded glycopolymer having also carboxylate (COO-) polyanions at the side chain. The polyanionic glycopolymer was then applied to a preparation of sugar-coated gold electrodes, which involves an alternating layer-by-layer adsorption based on electrostatic interactions. The presence of the Gb(2)-Coat on the surface was evidenced by Fourier transform infrared reflection absorption spectroscopy. The Gb(2)-coated glyco-chip was stable in 10 mM HEPES buffer containing 150 mM NaCl aq. Other glycopolymers carrying the beta-lactoside and alpha-D-mannopyranoside epitopes were applied to the same assembling process. The derived glycosyl arrays will be useful for detecting Shiga toxins, other pathogenic toxins and viruses when applied as glyco-chips for surface plasmon resonance or quartz crystal microbalance technique. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.03.102

文献信息

• Synthesis of N-functionalized oleamide derivatives
  作者：Yusuke Ohba、Yukiko Kanao、Mayuko Takatsuji、Motoki Ito、Norikazu Yabuta、Hiroshi Nojima、Yasuyuki Kita

  DOI：10.1016/j.tet.2007.02.074

  日期：2007.4

  Oleamide is an interesting compound, which shows various pharmacological activities including the inhibitory effect of gap junction formation. Recently, the studies of the gap junction have been some of the hot topics in biology and its inhibitors have become more useful tools [Cravatt, B. F.; Garcia, 0. P.; Siuzdak, G.; Gilula, N. B.; Henriksen, S. J.; Boger, D. L.; Lerner, R. A. Science 1995, 268, 1506-1509; Cravatt, B. F.; Lerner, R. A.; Boger, D. L. J. Am. Chem. Soc. 1996,118,580-590; Guan, X; Cravatt, B. F.; Ehring, G. R.; Hall, J. E.; Boger, D. L.; Lerner, R. A.; Gilula, N. B. J. Cell Biol. 1997,139,1785-1792; Boger, D. L.; Patterson, J. E.; Guan, X.; Cravatt, B. E; Lerner, R. A.; Gilula, N. B. Proc. Natl. Acad. Sci. U.S.A. 1998,95,4810-4815; Ito, A.; Morita, N.; Miura, D.; Koma, Y; Kataoka, T. R.; Yamasaki, H.; Kitamura, Y.; Kita, Y; Nojima, H. Carcinogenesis 2004, 25, 2015-2022]. However, many reports suggest that the functionalizations of oleamide to retain its biological activity were difficult [Boger, D. L.; Patterson, J. E.; Guan, X.; Cravatt, B. E; Lerner, R. A.; Gilula, N. B. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 4810-4815; Ito, A.; Morita, N.; Miura, D.; Koma, Y.; Kataoka, T. R.; Yamasaki, H.; Kitamura, Y.; Kita, Y; Nojima, H. Carcinogenesis 2004, 25, 2015-2022]. The synthesis of the functionalized oleamide derivatives, whose biological activity is not blocked, has become attractive in both the biological and chemical fields.Herein, by linking the fluorophore to the oleamide by alkyl chains, we synthesized the fluorescently tagged oleamide whose biological feature is similar to that of oleamide. Moreover, we also synthesized other bioactive derivatives tagged by other groups such as the sugars and biotin via alkyl chain linkers. (C) 2007 Elsevier Ltd. All rights reserved,