(S)-2-(((2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl)amino)-3-phenylpropanoic acid | 106138-35-6

• 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: (S)-2-(((2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl)amino)-3-phenylpropanoic acid
• 英文别名: N-(2,3,4,5,6-pentahydroxylhexyl)-L-phenylalanine
• CAS: 106138-35-6
• 化学式: C₁₅H₂₃NO₇
• 分子量: 329.35
• InChiKey: XKJPSLXJXHXYHR-ODXJTPSBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.29
• 重原子数：
  23.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  150.48
• 氢给体数：
  7.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  二硫化碳 、 (S)-2-(((2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl)amino)-3-phenylpropanoic acid 在 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 1.0h， 以80%的产率得到disodium N-(2,3,4,5,6-pentahydroxylhexyl)-N-dithiocarbamate-L-phenylalaninate
  参考文献：
  名称：

  Synthesis of Novel Chelating Agents and Their Effect on Cadmium Decorporation

  摘要：

  A series of novel dithiocarbamates, disodium salts of N-glucamyl-N-dithiocarboxyl-amino acids, were synthesized, and their usefullness as an antagonist of cadmium intoxication was investigated. These chelating agents were found to be effective in both acute and repeated exposure cadmium poisoning. The results showed that the cadmium mobilizing properties of disodium N-(2,3,4,5,6-pentahydroxylhexyl)-N-dithiocarbamate-L-threoninate and disodium N-(2,3,4,5,6-pentahydroxylhexyl)-N-dithiocarbamate-L-cysteinate are clearly superior to those of sodium N-(4-methoxybenzyl)-D-glucamine-N-carbodithioate (MeOBGDTC) revealed in the experiments described here. The toxicity of these novel compounds is modest, and their effect on the concentrations of essential metal ions in the renal cortex is quite small in comparison with that of a group treated with cadmium only. The new dithiocarbomates were identified by MS, rather than by elemental analysis, as they were extremely hygroscopic.

  DOI：

  10.1021/tx970134z
• 作为产物：
  描述：

  sodium N-(2,3,4,5,6-pentahydroxylhexylidene)-L-phenylalaninate 在 sodium tetrahydroborate 作用下， 反应 120.0h， 生成 (S)-2-(((2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl)amino)-3-phenylpropanoic acid
  参考文献：
  名称：

  Synthesis of Novel Chelating Agents and Their Effect on Cadmium Decorporation

  摘要：

  A series of novel dithiocarbamates, disodium salts of N-glucamyl-N-dithiocarboxyl-amino acids, were synthesized, and their usefullness as an antagonist of cadmium intoxication was investigated. These chelating agents were found to be effective in both acute and repeated exposure cadmium poisoning. The results showed that the cadmium mobilizing properties of disodium N-(2,3,4,5,6-pentahydroxylhexyl)-N-dithiocarbamate-L-threoninate and disodium N-(2,3,4,5,6-pentahydroxylhexyl)-N-dithiocarbamate-L-cysteinate are clearly superior to those of sodium N-(4-methoxybenzyl)-D-glucamine-N-carbodithioate (MeOBGDTC) revealed in the experiments described here. The toxicity of these novel compounds is modest, and their effect on the concentrations of essential metal ions in the renal cortex is quite small in comparison with that of a group treated with cadmium only. The new dithiocarbomates were identified by MS, rather than by elemental analysis, as they were extremely hygroscopic.

  DOI：

  10.1021/tx970134z

文献信息

• 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，