N-(2,3,4,5,6-pentahydroxylhexyl)-L-alanine | 91740-84-0

• 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: N-(2,3,4,5,6-pentahydroxylhexyl)-L-alanine
• 英文别名: N-(1-deoxy-D-glucitol-1-yl)-L-alanine；(2S)-2-[[(2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl]amino]propanoic acid
• CAS: 91740-84-0
• 化学式: C₉H₁₉NO₇
• 分子量: 253.252
• InChiKey: NEOSULLWWIOIGB-TVNFTVLESA-N

物化性质

• 沸点：
  628.0±55.0 °C(Predicted)
• 密度：
  1.490±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -5.6
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  151
• 氢给体数：
  7
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-(2,3,4,5,6-pentahydroxylhexyl)-L-alanine 、 三甲基硅咪唑 以 吡啶 为溶剂， 反应 2.0h， 生成 trimethylsilyl ((2R,3R,4R,5R)-2,3,4,5,6-pentakis((trimethylsilyl)oxy)hexyl)-L-alaninate
  参考文献：
  名称：

  通过质谱鉴定N-（1-脱氧己糖醇-1基）氨基酸，蛋白质的非酶糖基化参考化合物

  摘要：

  摘要通过质谱和气相色谱法研究了合成的N-（1-脱氧-d-葡萄糖醇-1-基）-和N-（1-脱氧-d-甘露醇-1-基）氨基酸的三甲基甲硅烷基衍生物。 -质谱。电子的撞击导致C-1和C-2之间以及羰基碳和α-碳原子之间的裂解，从而形成可识别分子氨基酸部分的离子。从化学电离光谱获得分子量，以氨作为反应气。这些方法将用于鉴定非对称糖基化蛋白的N-（1-脱氧-d-果糖-1-基）基团形成时形成的N-（1-脱氧己糖醇-1-基）氨基酸的氨基酸部分将其用硼氢化钠还原，并将产物在酸的存在下水解。

  DOI：

  10.1016/0008-6215(85)85147-8
• 作为产物：
  描述：

  sodium N-(2,3,4,5,6-pentahydroxylhexylidene)-L-alaninate 在 sodium tetrahydroborate 作用下， 反应 120.0h， 生成 N-(2,3,4,5,6-pentahydroxylhexyl)-L-alanine
  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

• Synthesis of N-(1-deoxyhexitol-1-yl)amino acids, reference compounds for the nonenzymic glycosylation of proteins
  作者：Donald J. Walton、Edward R. Ison、Walter A. Szarek

  DOI：10.1016/0008-6215(84)85082-x

  日期：1984.5

  The N-(1-deoxy-D-mannitol-1-yl) and N-(1-deoxy-D-glucitol-1-yl) derivatives of L-valine, L-alanine, L-threonine, and L-leucine were prepared by reductive amination of D-mannose and D-glucose with the appropriate amino acids, in the presence of sodium cyanoborohydride. N epsilon-(1-Deoxy-D-mannitol-1-yl)- and N epsilon-(1-deoxy-D-glucitol-1-yl)-L-lysine were prepared by similar reactions of hexoses

  L-缬氨酸，L-丙氨酸，L-苏氨酸和L-亮氨酸的N-（1-脱氧-D-甘露醇-1-基）和N-（1-脱氧-D-葡萄糖醇-1-基）衍生物在氰基硼氢化钠存在下，通过用适当的氨基酸还原胺化D-甘露糖和D-葡萄糖来制备糖。Nε-（1-脱氧-D-甘露醇-1-基）-和Nε-（1-脱氧-D-葡萄糖醇-1-基）-L-赖氨酸是通过己糖与Nα-叔胺的类似反应制备的-丁氧基羰基和Nα-苄氧基羰基-L-赖氨酸，然后除去保护基。结构通过1H-nmr光谱确认，表明每种化合物完全不含其C-2差向异构体。这些合成化合物可用作参考化合物，用于鉴定当非对称糖基化蛋白的N-（1-脱氧-D-果糖-1-基）基团形成时形成的N-（1-脱氧己糖醇-1-基）氨基酸，
• Synthesis of Novel Chelating Agents and Their Effect on Cadmium Decorporation
  作者：Chao Wang、Yiou Fang、Shiqi Peng、Dongxin Ma、Jinyuan Zhao

  DOI：10.1021/tx970134z

  日期：1999.4.1

  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.
• Identification by mass spectrometry of N-(1-deoxyhexitol-1yl)amino acids, reference compounds for the nonenzymic glycosylation of proteins
  作者：Donald J. Walton、Walter A. Szarek、David B. Maclean、Robert V. Gerard

  DOI：10.1016/0008-6215(85)85147-8

  日期：1985.3

  synthetic N -(1-deoxy- d -glucitol-1-yl)- and N -(1-deoxy- d -mannitol-1-yl)amino acids have been examined by mass spectrometry and gas—liquid chromatography—mass spectrometry. Electron impact resulted in cleavage between C-1 and C-2, and between the carbonyl carbon and α-carbon atom, to form ions that allow the amino acid portion of the molecule to be identified. Molecular weights were obtained from

  摘要通过质谱和气相色谱法研究了合成的N-（1-脱氧-d-葡萄糖醇-1-基）-和N-（1-脱氧-d-甘露醇-1-基）氨基酸的三甲基甲硅烷基衍生物。 -质谱。电子的撞击导致C-1和C-2之间以及羰基碳和α-碳原子之间的裂解，从而形成可识别分子氨基酸部分的离子。从化学电离光谱获得分子量，以氨作为反应气。这些方法将用于鉴定非对称糖基化蛋白的N-（1-脱氧-d-果糖-1-基）基团形成时形成的N-（1-脱氧己糖醇-1-基）氨基酸的氨基酸部分将其用硼氢化钠还原，并将产物在酸的存在下水解。