5-((2-(dansylamino)ethyl)thio)pent-1-yl 4-O-(6-O-((2-naphthyl)methyl)-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside | 1225440-66-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-((2-(dansylamino)ethyl)thio)pent-1-yl 4-O-(6-O-((2-naphthyl)methyl)-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside
• 英文别名: N-[2-[5-[(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(naphthalen-2-ylmethoxymethyl)oxan-2-yl]oxyoxan-2-yl]sulfanylpentylsulfanyl]ethyl]-5-(dimethylamino)naphthalene-1-sulfonamide
• CAS: 1225440-66-3
• 化学式: C₄₂H₅₆N₂O₁₂S₃
• 分子量: 877.111
• InChiKey: SIAZQINJGPVCHF-NYDGXXASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  59
• 可旋转键数：
  20
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  267
• 氢给体数：
  7
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  pent-4-en-1-yl 4-O-(6-O-((2-naphthyl)methyl)-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside 在 三乙胺 作用下， 以 甲醇 、 水 为溶剂， 反应 6.0h， 生成 5-((2-(dansylamino)ethyl)thio)pent-1-yl 4-O-(6-O-((2-naphthyl)methyl)-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Synthetic studies of bi-fluorescence-labeled maltooligosaccharides as substrates for α-amylase on the basis of fluorescence resonance energy transfer (FRET)

  摘要：

  A series of bi-fluorescence-labeled maltooligosaccharides that lead to fluorescence resonance energy transfer (FRET) was systematically synthesized. Effective FRETs were observed with all of the synthesized probes. Digestion of probes having tetra-, quintet-, hexa- or hepta-saccharidic chain lengths with human saliva alpha-amylase resulted in disappearance of FRET when an excitation wavelength of at 290 nm was used followed by detection at ca. 520 nm due to emission from the dansyl moiety. However, continuous FRET was observed when probes having di- or trisaccharidic chain lengths were used as substrates. In addition to the substrate characteristics based on saccharidic chain length, the reaction rates of digestion for the substrates by amylase were different and also depended on their saccharidic chain length. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.065

文献信息

• Simple and conveniently accessible bi-fluorescence-labeled substrates for amylases
  作者：Hiroyuki Oka、Tetsuo Koyama、Ken Hatano、Daiyo Terunuma、Koji Matsuoka

  DOI：10.1016/j.bmcl.2010.01.117

  日期：2010.3

  Synthesis of bi-fluorescence-labeled maltooligosaccharides for amylase assay was accomplished. Preliminary biological evaluation of both bi-fluorescence-labeled maltohexasaccharide and maltose using alpha-amylase was carried out, and the hexaosyl derivative showed unique variation on the basis of fluorescence resonance energy transfer (FRET). (C) 2010 Elsevier Ltd. All rights reserved.
• Synthetic studies of bi-fluorescence-labeled maltooligosaccharides as substrates for α-amylase on the basis of fluorescence resonance energy transfer (FRET)
  作者：Hiroyuki Oka、Tetsuo Koyama、Ken Hatano、Koji Matsuoka

  DOI：10.1016/j.bmc.2011.10.065

  日期：2012.1

  A series of bi-fluorescence-labeled maltooligosaccharides that lead to fluorescence resonance energy transfer (FRET) was systematically synthesized. Effective FRETs were observed with all of the synthesized probes. Digestion of probes having tetra-, quintet-, hexa- or hepta-saccharidic chain lengths with human saliva alpha-amylase resulted in disappearance of FRET when an excitation wavelength of at 290 nm was used followed by detection at ca. 520 nm due to emission from the dansyl moiety. However, continuous FRET was observed when probes having di- or trisaccharidic chain lengths were used as substrates. In addition to the substrate characteristics based on saccharidic chain length, the reaction rates of digestion for the substrates by amylase were different and also depended on their saccharidic chain length. (C) 2011 Elsevier Ltd. All rights reserved.