7,8a-dihydroxy-4a-methyl-8-(α-D-glucopyranosyloxy)hexahydro-5-oxa-4-thia-1-azanaphthalene-2-carboxylic acid

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7,8a-dihydroxy-4a-methyl-8-(α-D-glucopyranosyloxy)hexahydro-5-oxa-4-thia-1-azanaphthalene-2-carboxylic acid
• 英文别名: 7,8a-dihydroxy-4a-methyl-8-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,3,6,7,8-hexahydropyrano[2,3-b][1,4]thiazine-2-carboxylic acid
• 化学式: C₁₅H₂₅NO₁₁S
• 分子量: 427.43
• InChiKey: HTQFDPUJZPBJBB-BZLKVGDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  224
• 氢给体数：
  8
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  7,8a-dihydroxy-4a-methyl-8-(α-D-glucopyranosyloxy)hexahydro-5-oxa-4-thia-1-azanaphthalene-2-carboxylic acid 在 盐酸 作用下， 反应 1.0h， 以5.8%的产率得到1-[3-(α-D-glucopyranosyloxy)-2-furanyl]-1-ethanone
  参考文献：
  名称：

  Characterization of a New Maillard Type Reaction Product Generated by Heating 1-Deoxymaltulosyl-glycine in the Presence of Cysteine

  摘要：

  The reaction between Amadori compounds and cysteine was investigated. When 1-deoxymaltulosyl-glycine (glycyl-fructosyl-glucose) was heated at 100 degrees C with cysteine in a neutral aqueous solution, a novel intermediate composed of 1-deoxyosone and cysteine was detected. NMR and mass spectrometry studies revealed the structure of the isolated intermediate to be 7,8a-dihydroxy-4a-methyl8-(alpha-D-glucopyranosyloxy)hexahydro-5-oxa-4-thia-1-azanaphthalene-2-carboxylic acid. This intermediate easily generated isomaltol and acetylfuran as volatile compounds in 1 mol/L HCl at 100 degrees C.

  DOI：

  10.1021/jf060296d
• 作为产物：
  描述：

  麦芽糖 在 sodium hydroxide 、 sodium hydrogensulfite 、 溶剂黄146 作用下， 以 甲醇 、 乙二醇 为溶剂， 反应 7.5h， 生成 7,8a-dihydroxy-4a-methyl-8-(α-D-glucopyranosyloxy)hexahydro-5-oxa-4-thia-1-azanaphthalene-2-carboxylic acid
  参考文献：
  名称：

  Characterization of a New Maillard Type Reaction Product Generated by Heating 1-Deoxymaltulosyl-glycine in the Presence of Cysteine

  摘要：

  The reaction between Amadori compounds and cysteine was investigated. When 1-deoxymaltulosyl-glycine (glycyl-fructosyl-glucose) was heated at 100 degrees C with cysteine in a neutral aqueous solution, a novel intermediate composed of 1-deoxyosone and cysteine was detected. NMR and mass spectrometry studies revealed the structure of the isolated intermediate to be 7,8a-dihydroxy-4a-methyl8-(alpha-D-glucopyranosyloxy)hexahydro-5-oxa-4-thia-1-azanaphthalene-2-carboxylic acid. This intermediate easily generated isomaltol and acetylfuran as volatile compounds in 1 mol/L HCl at 100 degrees C.

  DOI：

  10.1021/jf060296d

文献信息

• Characterization of a New Maillard Type Reaction Product Generated by Heating 1-Deoxymaltulosyl-glycine in the Presence of Cysteine
  作者：Masafumi Ota、Masanori Kohmura、Hirokazu Kawaguchi

  DOI：10.1021/jf060296d

  日期：2006.7.1

  The reaction between Amadori compounds and cysteine was investigated. When 1-deoxymaltulosyl-glycine (glycyl-fructosyl-glucose) was heated at 100 degrees C with cysteine in a neutral aqueous solution, a novel intermediate composed of 1-deoxyosone and cysteine was detected. NMR and mass spectrometry studies revealed the structure of the isolated intermediate to be 7,8a-dihydroxy-4a-methyl8-(alpha-D-glucopyranosyloxy)hexahydro-5-oxa-4-thia-1-azanaphthalene-2-carboxylic acid. This intermediate easily generated isomaltol and acetylfuran as volatile compounds in 1 mol/L HCl at 100 degrees C.