Fructose-methionine Amadori intermediate | 87251-88-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Fructose-methionine Amadori intermediate
• 英文别名: 1-(L-methionine)-1-deoxy-D-fructose；(2S)-4-methylsulfanyl-2-[[(2R,3S,4R,5R)-2,3,4,5-tetrahydroxyoxan-2-yl]methylamino]butanoic acid
• CAS: 87251-88-5
• 化学式: C₁₁H₂₁NO₇S
• 分子量: 311.356
• InChiKey: FXJNVRSZTVTJQW-OKZKDYFGSA-N

物化性质

• 沸点：
  566.1±50.0 °C(Predicted)
• 密度：
  1.516±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.2
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  165
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Fructose-methionine Amadori intermediate 反应 0.08h， 以70%的产率得到3-甲硫基丙醛
  参考文献：
  名称：

  Kinetics and thermal degradation of the fructose-methionine Amadori intermediates. GC-MS/SPECMA data bank identification of volatile aroma compounds

  摘要：

  Fructose-methionine Amadori intermediates. prepared from D-glucose and L-methionine, were purified by semi-preparative HPLC. Structural elucidation was achieved by C-13-NMR and mass spectrometry in the FAB+ and FAB- modes. Constant rates of formation of glucosylamine and the Amadori intermediate, and their thermal degradation into reductones and methionine as well as into diglucosylamine, were observed. Thermal degradation of the Amadori intermediate gives not only the well-known degradation products of the sugar moiety and methional (from the Strecker degradation of methionine), but also several heterocyclic compounds (pyridines, pyrazines. pyrroles, and furans). Some of them contain a methylthiopropyl group in their side chain. These new compounds were identified by the fragmentation rules and the Kovats index additive properties. Out of the 80 compounds isolated, approximately 70 were identified.

  DOI：

  10.1016/s0008-6215(00)90510-x
• 作为产物：
  描述：

  2,3:4,5-bis-O-(isopropylidene)-D-fructopyranose aldehyde 、 L-蛋氨酸 在 sodium hydroxide 、 sodium cyanoborohydride 作用下， 以 水 为溶剂， 反应 16.0h， 以81%的产率得到Fructose-methionine Amadori intermediate
  参考文献：
  名称：

  通过六氨基-2-己糖的还原胺化合成N-（1-脱氧-d-果糖-1-基）氨基酸的途径

  摘要：

  摘要描述了两种合成1-缬氨酸，1-亮氨酸，1-甲硫氨酸，1-苯丙氨酸和6-氨基己酸的N-（1-脱氧d-果糖-1-基）衍生物的途径。一种途径涉及在氰基硼氢化钠存在下对d-阿拉伯糖-己基-2-己糖的还原胺化。产量受到难以去除的大量N-（1-脱氧己糖醇-1-基）氨基酸形成的限制。在第二种方法中克服了这一缺点，该方法涉及2，3：4，5-二-O-异亚丙基-醛-β-d-阿拉伯糖-己二-2-ulo-2，6-吡喃糖的还原胺化。在去封闭步骤之后，获得上述氨基酸的N-（1-脱氧-d-果糖-1-基）衍生物，其收率至少是目前涉及氨基酸与d的反应的报道方法的两倍。 -葡萄糖，

  DOI：

  10.1016/0008-6215(87)80273-2

文献信息

• Electrospray positive ionization tandem mass spectrometry of Amadori compounds
  作者：Jun Wang、Yi-Min Lu、Bai-Zhan Liu、He-Yong He

  DOI：10.1002/jms.1290

  日期：2008.2
• Synthetic routes to N-(1-deoxy-d-fructos-1-yl)amino acids by way of reductive amination of hexos-2-uloses
  作者：Donald J. Walton、John D. McPherson、Torsten Hvidt、Walter A. Szarek

  DOI：10.1016/0008-6215(87)80273-2

  日期：1987.9

  overcome in the second route, which involved reductive amination of 2,3:4,5-di- O -isopropylidene- aldehydo -β- d - arabino -hexos-2-ulo-2,6-pyranose; following a deblocking step, N -(1-deoxy- d -fructos-1-yl) derivatives of the aforementioned amino acids were obtained in yields which were at least double those reported for the current procedure involving the reaction of an amino acid with d -glucose, and

  摘要描述了两种合成1-缬氨酸，1-亮氨酸，1-甲硫氨酸，1-苯丙氨酸和6-氨基己酸的N-（1-脱氧d-果糖-1-基）衍生物的途径。一种途径涉及在氰基硼氢化钠存在下对d-阿拉伯糖-己基-2-己糖的还原胺化。产量受到难以去除的大量N-（1-脱氧己糖醇-1-基）氨基酸形成的限制。在第二种方法中克服了这一缺点，该方法涉及2，3：4，5-二-O-异亚丙基-醛-β-d-阿拉伯糖-己二-2-ulo-2，6-吡喃糖的还原胺化。在去封闭步骤之后，获得上述氨基酸的N-（1-脱氧-d-果糖-1-基）衍生物，其收率至少是目前涉及氨基酸与d的反应的报道方法的两倍。 -葡萄糖，
• Kinetics and thermal degradation of the fructose-methionine Amadori intermediates. GC-MS/SPECMA data bank identification of volatile aroma compounds
  作者：Gaston Vernin、Jacques Metzger、Christian Boniface、Marie-Hélène Murello、Antoine Siouffi、Jean-Louis Larice、Cyril Párkányi

  DOI：10.1016/s0008-6215(00)90510-x

  日期：1992.6

  Fructose-methionine Amadori intermediates. prepared from D-glucose and L-methionine, were purified by semi-preparative HPLC. Structural elucidation was achieved by C-13-NMR and mass spectrometry in the FAB+ and FAB- modes. Constant rates of formation of glucosylamine and the Amadori intermediate, and their thermal degradation into reductones and methionine as well as into diglucosylamine, were observed. Thermal degradation of the Amadori intermediate gives not only the well-known degradation products of the sugar moiety and methional (from the Strecker degradation of methionine), but also several heterocyclic compounds (pyridines, pyrazines. pyrroles, and furans). Some of them contain a methylthiopropyl group in their side chain. These new compounds were identified by the fragmentation rules and the Kovats index additive properties. Out of the 80 compounds isolated, approximately 70 were identified.