DL-2,4-二氨基戊二酸 | 1421-04-1

• 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: DL-2,4-二氨基戊二酸
• 英文名称: 2,4-diaminopentanedioic acid
• 英文别名: 2,4-diamino-glutaric acid；2,4-Diamino-glutarsaeure；threo-2,4-diaminopentanedioic acid
• CAS: 1421-04-1
• 化学式: C₅H₁₀N₂O₄
• mdl: MFCD00192792
• 分子量: 162.145
• InChiKey: LOPLXECQBMXEBQ-UHFFFAOYSA-N

物化性质

• 熔点：
  270-280 °C (decomp)
• 沸点：
  391.2±42.0 °C(Predicted)
• 密度：
  1.495±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -6.6
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  127
• 氢给体数：
  4
• 氢受体数：
  6

安全信息

• 海关编码：
  2922499990

反应信息

• 作为反应物：
  描述：

  DL-2,4-二氨基戊二酸 在 lithium hydroxide 、 氯化亚砜 、 偶氮二甲酸二异丙酯 、 dimethyl sulfide borane 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 30.5h， 生成 trans-4-carboxy-6-(mercaptomethyl)-3,4,5,6-tetrahydropyrimidin-2(1H)-one
  参考文献：
  名称：

  cis-4-Carboxy-6-(mercaptomethyl)-3,4,5,6-tetrahydropyrimidin-2(1H)-one, a potent inhibitor of mammalian dihydroorotase

  摘要：

  A series of cis- and trans-4-carboxy-3,4,5,6-tetrahydropyrimidin-2(1H)-ones possessing either a carboxy, hydroxymethyl, or mercaptomethyl substituent at C-6 were prepared and tested for their ability to inhibit mammalian dihydroorotase. Of these compounds, only the cis-6-mercaptomethyl compound, cis-1, was found to be a potent competitive inhibitor of the enzyme (Ki = 140 nM at pH 7.4 and 8.5) when assayed in the direction of dihydro-L-orotate hydrolysis. These results suggest that the inhibition arises from the ligation of the thiolate to the zinc atom which is thought to be located in the enzyme's active site. Although analysis of cis-1 with 2,2'-dithiobis(5-nitrobenzoic acid) revealed significant loss of the free thiol group under enzymatic assay conditions, the addition of the reducing agent, dithiothreitol, to the enzymatic reaction mixtures afforded cis-1 complete protection against this chemical decomposition, as evidenced by lowering of the inhibition constant in the presence of dithiothreitol. Compound cis-1 had no significant antiproliferative activity against B16 melanoma cells in tissue culture, possibly due to the rapid decomposition of the compound or poor permeability into cells.

  DOI：

  10.1021/jm00402a018
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 乙醇 、 镍 作用下， 60.0~115.0 ℃ 、24.51 MPa 条件下， 生成 DL-2,4-二氨基戊二酸
  参考文献：
  名称：

  Carter; Van Abeele; Rothrock, Journal of Biological Chemistry, 1949, vol. 178, p. 329

  摘要：

  DOI：

文献信息

• Fluorine containing amino acids and their derivatives. 7. Synthesis and antitumor activity of α- and γ-substituted methotrexate analogs
  作者：Tadahiko Tsushima、Kenji Kawada、Shoichi Ishihara、Naomi Uchida、Osamu Shiratori、Junko Higaki、Masaharu Hirata

  DOI：10.1016/s0040-4020(01)86044-0

  日期：1988.1

  afforded a number of fluorine containing α amino acids such as β-fluorinated-alanines, 2-amino-n,n,n-trifluoroalkanoic acids, and fluorinated glutamic acids as well as other γ-heteroatom substituted glutamic acids. Here, an efficient enzymatic optical resolution using hog kidney acylase was conducted to obtain both optical isomers of 2-amino-n,n,n-trifluoroalkanoic acids. In addition, a novel sulfoxide

  α-取代的丙二酸酯的三种类型的反应，二氟甲基化，与n，n，n-三氟烷基磺酸酯的烷基化以及与2-取代的丙烯酸酯的Michael加成反应，可方便地得到许多含氟的α氨基酸，​​例如β-氟代丙氨酸。 ，2-氨基-n，n，n-三氟链烷酸和氟化谷氨酸以及其他γ-杂原子取代的谷氨酸。在此，进行了使用猪肾酰基转移酶的有效酶促光学拆分，以获得2-氨基-n，n，n-三氟链烷酸的两种旋光异构体。另外，在α-二氟甲基-α-亚磺酰丙二酸二乙酯的碱催化反应中观察到了新的亚砜重排。最后，获得的α-和γ-取代的谷氨酸用于抗肿瘤药甲氨蝶呤的化学修饰，以显示出显着的构效关系。特别是，氟取代对观察到体内抗肿瘤活性。
• Synthesis of stereoisomers of 2,4-diaminoglutaric and 2,5-diaminoadipic acids
  作者：V. P. Krasnov、E. A. Zhdanova、M. A. Korolyova、I. M. Bukrina、M. I. Kodess、V. Kh. Kravtsov、V. N. Biyushkin

  DOI：10.1007/bf02494371

  日期：1997.2

  Stereoisomers of 2,4-diaminoglutaric and 2,5-diaminoadipic acids were synthesized from glutamic and 2-aminoadipic acids, respectively. The stereochemistry of the products was established by IH NMR spectroscopy and X-ray analysis.
• Hellmann,H. et al., Justus Liebigs Annalen der Chemie, 1960, vol. 631, p. 76 - 81
  作者：Hellmann,H. et al.

  DOI：——

  日期：——
• Weygand,F.; Spiess,B., Chemische Berichte, 1964, vol. 97, p. 3456 - 3460
  作者：Weygand,F.、Spiess,B.

  DOI：——

  日期：——
• Hellmann et al., Chemische Berichte, 1956, vol. 89, p. 2433,2435
  作者：Hellmann et al.

  DOI：——

  日期：——