N-(1-脱氧-D-果糖-1-基)-L-苯丙氨酸 | 71887-77-9

• 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
• 中文名称: N-(1-脱氧-D-果糖-1-基)-L-苯丙氨酸
• 英文名称: N-(1-deoxy-D-fructos-1-yl)-L-phenylalanine
• 英文别名: N-(1-deoxy-beta-D-fructopyranos-1-yl)-L-phenylalanine；(2S)-3-phenyl-2-[[(2R,3S,4R,5R)-2,3,4,5-tetrahydroxyoxan-2-yl]methylamino]propanoic acid
• CAS: 71887-77-9
• 化学式: C₁₅H₂₁NO₇
• 分子量: 327.334
• InChiKey: CPXVOVGNKRERLG-IHWVXMPCSA-N

物化性质

• 熔点：
  118-120 °C
• 沸点：
  562.3±50.0 °C(Predicted)
• 密度：
  1.494±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.3
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  140
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-(1-脱氧-D-果糖-1-基)-L-苯丙氨酸 反应 0.01h， 生成 3-苯基吡啶 、 3,5-二苯基吡啶 、 N-phenethylnaphthalen-1-amine 、 苯乙醛 、 1-萘胺 、 N-methyl-N-phenethylnaphthalen-1-amine 、 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  Pyrolysis/GC/MS Analysis of N-(1-Deoxy-d-fructos-1-yl)-l-phenylalanine:  Identification of Novel Pyridine and Naphthalene Derivatives

  摘要：

  Pyrolysis/GC/MS has been employed to analyze phenylalanine specific products formed during Maillard reaction. Phenylalanine Amadori product and different model systems containing phenylalanine and glucose, ribose, or glycerladehyde were studied. Ribbon pyrolysis was used to study the effect of temperature (150, 200, 250 degrees C) on the efficiency of formation of initial pyrolysis products from phenylalanine and Amadori phenylalanine. Quartz tube pyrolysis was used at 250 degrees C to enhance the secondary reactions. To address specific mechanistic questions, [1-C-13]glucose was used. These studies revealed the formation of pyridine and naphthalene derivatives such as 3,5-diphenylpyridine, 1(2)-naphthaleneamine, N-methyl-1(2)-aminonaphthalene, 1-aminoanthracene, 2'-phenylpyrrolo [4,5-a] dihydronaphthalene, 1(2)-(N-phenethyl)naphthaleneamine, and 1(2)-(N-phenethyl-N-methyl)naphthaleneamine. The precursors for pyridine and naphthalene derivatives were verified by GC/MS identification of the target compounds in the reaction mixtures of the postulated precursors.

  DOI：

  10.1021/jf950418u
• 作为产物：
  描述：

  2,3:4,5-bis-O-(isopropylidene)-D-fructopyranose aldehyde 、 L-苯丙氨酸 在 sodium hydroxide 、 sodium cyanoborohydride 作用下， 以 水 为溶剂， 反应 16.0h， 以63%的产率得到N-(1-脱氧-D-果糖-1-基)-L-苯丙氨酸
  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，
• Pyrolysis/GC/MS Analysis of <i>N</i>-(1-Deoxy-<scp>d</scp>-fructos-1-yl)-<scp>l</scp>-phenylalanine:  Identification of Novel Pyridine and Naphthalene Derivatives
  作者：Anahita Keyhani、Varoujan A. Yaylayan

  DOI：10.1021/jf950418u

  日期：1996.1.1

  Pyrolysis/GC/MS has been employed to analyze phenylalanine specific products formed during Maillard reaction. Phenylalanine Amadori product and different model systems containing phenylalanine and glucose, ribose, or glycerladehyde were studied. Ribbon pyrolysis was used to study the effect of temperature (150, 200, 250 degrees C) on the efficiency of formation of initial pyrolysis products from phenylalanine and Amadori phenylalanine. Quartz tube pyrolysis was used at 250 degrees C to enhance the secondary reactions. To address specific mechanistic questions, [1-C-13]glucose was used. These studies revealed the formation of pyridine and naphthalene derivatives such as 3,5-diphenylpyridine, 1(2)-naphthaleneamine, N-methyl-1(2)-aminonaphthalene, 1-aminoanthracene, 2'-phenylpyrrolo [4,5-a] dihydronaphthalene, 1(2)-(N-phenethyl)naphthaleneamine, and 1(2)-(N-phenethyl-N-methyl)naphthaleneamine. The precursors for pyridine and naphthalene derivatives were verified by GC/MS identification of the target compounds in the reaction mixtures of the postulated precursors.