n-pentenyl <6-O-(2-naphthylmethyl)-β-D-galactopyranosyl>-(1<*>4)-β-D-glucopyranoside | 161767-04-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: n-pentenyl <6-O-(2-naphthylmethyl)-β-D-galactopyranosyl>-(1<*>4)-β-D-glucopyranoside
• CAS: 161767-04-0
• 化学式: C₂₈H₃₈O₁₁
• 分子量: 550.603
• InChiKey: RCCYHDXWXLKUSI-HYNLFBJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.03
• 重原子数：
  39.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  167.53
• 氢给体数：
  6.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  n-pentenyl <6-O-(2-naphthylmethyl)-β-D-galactopyranosyl>-(1<*>4)-β-D-glucopyranoside 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 72.5h， 生成 5-<2-(5-dimethylamino-1-naphthalenesulfonamido)ethanethio>pentyl <6-O-(2-naphthylmethyl)-β-D-galactopyranosyl>-(1<*>4)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of bi-fluorescence-labeled lactoside: A substrate for continual assay of ceramide glycanase

  摘要：

  A bi-fluorescence labeled derivative suitable for analysis of ceramide glycanase activity was constructed from 4-pentenyl lactoside. Selective modification of the galactosyl residue was attained by formation of 4',6'-naphthylmethylidene derivative, which was followed by regioselective reductive ring opening. The aglycon was extended by Michael addition of 2-aminoethanetiol, and dansylated at the terminal amino group. Excitation of the naphthyl group results in emission from the dansyl group, while the emission from the naphthyl group is quenched by the dansyl group. Upon digestion with ceramide glycanase, the energy transfer is severed and a decrease in the dansyl emission concommitant with an increase in the naphthyl emission was observed. This substrate was successfully used to analyze ceramide glycanase activity.

  DOI：

  10.1016/s0957-4166(00)80383-3
• 作为产物：
  描述：

  在 吡啶 、 三氯化铝 、 硼烷-三甲胺络合物 、 4 A molecular sieve 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 67.0h， 生成 n-pentenyl <6-O-(2-naphthylmethyl)-β-D-galactopyranosyl>-(1<*>4)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of bi-fluorescence-labeled lactoside: A substrate for continual assay of ceramide glycanase

  摘要：

  A bi-fluorescence labeled derivative suitable for analysis of ceramide glycanase activity was constructed from 4-pentenyl lactoside. Selective modification of the galactosyl residue was attained by formation of 4',6'-naphthylmethylidene derivative, which was followed by regioselective reductive ring opening. The aglycon was extended by Michael addition of 2-aminoethanetiol, and dansylated at the terminal amino group. Excitation of the naphthyl group results in emission from the dansyl group, while the emission from the naphthyl group is quenched by the dansyl group. Upon digestion with ceramide glycanase, the energy transfer is severed and a decrease in the dansyl emission concommitant with an increase in the naphthyl emission was observed. This substrate was successfully used to analyze ceramide glycanase activity.

  DOI：

  10.1016/s0957-4166(00)80383-3

文献信息

• A bi-fluorescence-labeled substrate for ceramide glycanase based on fluorescence energy transfer
  作者：Koji Matsuoka、Shin-Ichiro Nishimura、Yuan C. Lee

  DOI：10.1016/0008-6215(95)00238-o

  日期：1995.10

  An alkyl lactoside containing two different fluorescence probes as an energy donor and an energy acceptor was synthesized as a substrate for ceramide glycanase. n-Pentenyl beta-lactoside was converted into its 4',6'-O-(2-naphthylmethylidene) derivative with subsequent benzoylation of all remaining OH groups. The fully protected lactoside was treated with borane-trimethylamine complex and aluminum chloride in tetrahydrofuran [P.J. Garegg, Pure Appl. Chem., 56 (1984) 845-858] for selective opening of the 4',6'-acetal group to give the 6'-O-(2-naphthylmethyl) derivative in high yield, After O-debenzoylation, the omega-alkenyl group at the reducing end was extended by Michael addition with HS(CH2)(2)NH2 . HCl to provide an amino group at the terminal position. The amino group was then dansylated to give the target lactoside, which has two different fluorescent probes at each end, Excitation at 290 nm (of the 2-naphthyl group) of the bi-fluorescence-labeled lactoside showed emissions at 335 nm (2-naphthyl) and at 540 nm (dansyl). The distance between the naphthyl group and the dansyl group was estimated to be 12 Angstrom by the Forster relationship. Digestion of this lactoside with American leech (Macrobdella decora) ceramide glycanase [B. Zhou et al., J. Biol. Chem., 264 (1989) 12,272-12,277] resulted in an increase in the naphthyl emission with a concomitant decrease in the dansyl emission, These changes can be used for continuous monitoring of the ceramide glycanase activity.