2-[[(2R,3S,4R,5R)-2,3,5-三羟基-4-[(2R,3R,4S,5S,6R)-3,4,5-三羟基-6-(羟基甲基)四氢吡喃-2-基]氧基四氢吡喃-2-基]甲基氨基]乙酸 | 142937-59-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-[[(2R,3S,4R,5R)-2,3,5-三羟基-4-[(2R,3R,4S,5S,6R)-3,4,5-三羟基-6-(羟基甲基)四氢吡喃-2-基]氧基四氢吡喃-2-基]甲基氨基]乙酸
• 中文别名: 噻唑并[5,4-d]异噻唑(9CI)
• 英文名称: 1-deoxymaltulosyl-glycine
• 英文别名: 1-Desoxy-1-glycinomaltose；2-[[(2R,3S,4R,5R)-2,3,5-trihydroxy-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methylamino]acetic acid
• CAS: 142937-59-5
• 化学式: C₁₄H₂₅NO₁₂
• 分子量: 399.352
• InChiKey: PUZZDKPXMUSJCH-UUWQLDJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.9
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  219
• 氢给体数：
  9
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  2-[[(2R,3S,4R,5R)-2,3,5-三羟基-4-[(2R,3R,4S,5S,6R)-3,4,5-三羟基-6-(羟基甲基)四氢吡喃-2-基]氧基四氢吡喃-2-基]甲基氨基]乙酸 在 盐酸 、 sodium hydroxide 作用下， 反应 4.0h， 生成 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 、 聚甘氨酸 在 sodium hydrogensulfite 、 溶剂黄146 作用下， 以 甲醇 、 乙二醇 为溶剂， 反应 4.5h， 以44%的产率得到2-[[(2R,3S,4R,5R)-2,3,5-三羟基-4-[(2R,3R,4S,5S,6R)-3,4,5-三羟基-6-(羟基甲基)四氢吡喃-2-基]氧基四氢吡喃-2-基]甲基氨基]乙酸
  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.