DL-erythro-3-hydroxy-aspartic acid diamide | 66619-99-6

• 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: DL-erythro-3-hydroxy-aspartic acid diamide
• 英文别名: (+/-)-erythro-3-Amino-2-hydroxy-bernsteinsaeure-diamid；DL-erythro-3-Hydroxy-asparaginsaeure-diamid；erythro-Hydroxy-DL-aspartic acid-diamid；(2R,3S)-2-amino-3-hydroxybutanediamide
• CAS: 66619-99-6；66620-00-6
• 化学式: C₄H₉N₃O₃
• 分子量: 147.134
• InChiKey: QWDNDSCSHXTTPP-NCGGTJAESA-N

物化性质

• 沸点：
  556.9±50.0 °C(Predicted)
• 密度：
  1.499±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.4
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  132
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  DL-erythro-3-hydroxy-aspartic acid diamide 、 碳酸二叔丁酯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 DMF (N,N-dimethyl-formamide) 为溶剂， 反应 4.0h， 生成 tert-butyl N-[(2R,3S)-1,4-diamino-3-hydroxy-1,4-dioxobutan-2-yl]carbamate
  参考文献：
  名称：

  Process for the production of pentostatin aglycone and pentostatin

  摘要：

  揭示了一种用于制备戊糖核苷和其类似物的新型、可扩展和改进的工艺。该方法包括从市售的L-二烷基酒石酸盐合成核碱的对映体特异性合成。

  公开号：

  US20040181052A1
• 作为产物：
  描述：

  (4R,5S)-4-氨基-3-氧代-1,2-恶唑烷-5-甲酰胺 在 platinum(IV) oxide 氢气 作用下， 生成 DL-erythro-3-hydroxy-aspartic acid diamide
  参考文献：
  名称：

  5-Carboxamido-4-amino-3-isoxazolidone, an asparagine analog

  摘要：

  trans-Aziridine-2,3-dicarboxylic ester was used to prepare the required beta-chlorohydroxamic acid used in the synthesis of the title compound. The trans configuration of the asparagine analogue was established by hydrogenolysis to erythro-beta-hydroxyasparagine amide. Neither the title compound nor the intermediate aziridinehydroxamic acid (8) showed significant activity against the L1210 and P-388 tumors. The title compound was inactive as an inhibitor of asparagine synthetase from Novikoff hepatoma and did not inhibit the growth of some 25 bacteria and fungi.

  DOI：

  10.1021/jm00205a026

文献信息

• Resolution of Amino Acids. IX. Studies on the Preparation of β-Hydroxyasparagines and Configuration of Natural Hydroxyasparagine
  作者：Hideo Okai、Nobuo Izumiya

  DOI：10.1246/bcsj.42.3550

  日期：1969.12

  Crystalline threo-and erythro-β-hydroxy-l-asparagine were prepared via asymmetric hydrolysis of the corresponding hydroxy-l-aspartic acid diamide by leucine aminopeptidase. The isomers of hydroxy-l-asparagine obtained were compared with the natural hydroxyasparagine isolated from human urine with respect to optical rotation and chromatography. From the results it is concluded that the spacial configuration of the natural product is that of erythro-β-hydroxy-l-asparagine. Additional studies were also carried out to prepare threo- and erythro-β-hydroxy-Dl-asparagine from the corresponding hydroxy-Dl-aspartic acid diamide without the enzyme.

  通过使用白氨酸氨肽酶对相应的羟基-L-天冬氨酸二酰胺进行不对称水解，制备了结晶的threo和erythro-β-羟基-L-天冬氨酸。获得的羟基-L-天冬氨酸异构体在光学旋转和色谱方面与从人尿中分离出的天然羟基天冬氨酸进行了比较。结果表明，天然产物的空间构型为erythro-β-羟基-L-天冬氨酸。此外，还进行了额外的研究，以在没有酶的情况下从相应的羟基-Dl-天冬氨酸二酰胺制备threo和erythro-β-羟基-Dl-天冬氨酸。
• Chibnall; Cannan, Biochemical Journal, 1930, vol. 24, p. 953
  作者：Chibnall、Cannan

  DOI：——

  日期：——
• Process for the production of pentostatin aglycone and pentostatin
  申请人：——

  公开号：US20040181052A1

  公开（公告）日：2004-09-16

  A novel, scaleable and improved process for preparing pentostatin and its analogs is disclosed. The method comprises the diastereospecific synthesis of the nucleobase from commercially available L-Dialkyl tartarates.

  揭示了一种用于制备戊糖核苷和其类似物的新型、可扩展和改进的工艺。该方法包括从市售的L-二烷基酒石酸盐合成核碱的对映体特异性合成。
• 5-Carboxamido-4-amino-3-isoxazolidone, an asparagine analog
  作者：Charles H. Stammer、Masayuki Sato

  DOI：10.1021/jm00205a026

  日期：1978.7

  trans-Aziridine-2,3-dicarboxylic ester was used to prepare the required beta-chlorohydroxamic acid used in the synthesis of the title compound. The trans configuration of the asparagine analogue was established by hydrogenolysis to erythro-beta-hydroxyasparagine amide. Neither the title compound nor the intermediate aziridinehydroxamic acid (8) showed significant activity against the L1210 and P-388 tumors. The title compound was inactive as an inhibitor of asparagine synthetase from Novikoff hepatoma and did not inhibit the growth of some 25 bacteria and fungi.