L-Allothreonin

• 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: L-Allothreonin
• 英文别名: 2-amino-3-hydroxy-butyric acid；(3S)-2-Amino-3-hydroxybutanoic acid
• 化学式: C₄H₉NO₃
• 分子量: 119.12
• InChiKey: AYFVYJQAPQTCCC-SCQFTWEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  83.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  二碳酸二叔丁酯 、 L-Allothreonin 在 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以100%的产率得到N-a-t.-Boc-D-threonine
  参考文献：
  名称：

  Antiplasmodial activity of new 4-aminoquinoline derivatives against chloroquine resistant strain

  摘要：

  Emergence and spread of multidrug resistant strains of Plasmodium falciparum has severely limited the antimalarial chemotherapeutic options. In order to overcome the obstacle, a set of new side-chain modified 4-aminoquinolines were synthesized and screened against chloroquine-sensitive (3D7) and chloroquine-resistant (K1) strains of P. falciparum. The key feature of the designed molecules is the use of methylpiperazine linked α, β(3)- and γ-amino acids to generate novel side chain modified 4-aminoquinoline analogues. Among the evaluated compounds, 20c and 30 were found more potent than CQ against K1 and displayed a four-fold and a three-fold higher activity respectively, with a good selectivity index (SI=5846 and 11,350). All synthesized compounds had resistance index between 1.06 and >14.13 as against 47.2 for chloroquine. Biophysical studies suggested that this series of compounds act on heme polymerization target.

  DOI：

  10.1016/j.bmc.2014.05.024

文献信息

• Preparation of Optically Active Allothreonine by Separating from a Diastereoisomeric Mixture with Threonine
  作者：Tatsuo YAJIMA、Serina ICHIMURA、Shirabe HORII、Tadashi SHIRAIWA

  DOI：10.1271/bbb.100295

  日期：2010.10.23

  A simple procedure is described to obtain D- and L-allothreonine (D- and L-aThr). A mixture of N-acetyl-D-allothreonine (Ac-D-aThr) and N-acetyl-L-threonine (Ac-L-Thr) was converted to a mixture of their ammonium salts and then treated with ethanol to precipitate ammonium N-acetyl-L-threoninate (Ac-L-Thr·NH(3)) as the less-soluble diastereoisomeric salt. After separating Ac-L-Thr·NH(3) by filtration

  描述了一种简单的程序以获得D-和L-Alsoreonine（D-和L-aThr）。将N-乙酰基-D-Allothreonine（Ac-D-aThr）和N-乙酰基-L-苏氨酸（Ac-L-Thr）的混合物转化成其铵盐的混合物，然后用乙醇处理以沉淀出N -乙酰基-L-苏氨酸盐（Ac-L-Thr·NH（3））为难溶的非对映异构体盐。过滤分离Ac-L-Thr·NH（3）后，将从滤液中获得的Ac-D-aThr在盐酸中水解，得到D-aThr为80％de，从水中重结晶，得到D-aThr> 99 ％de。从Ac-L-aThr和Ac-D-Thr的铵盐的混合物以类似方式获得L-aThr。
• Synthesis and immunomodulatory activity of novel amino acid analogues of fluoxetine
  作者：Mamta N. Talati、Sravanthi Vemireddy、Siva Deepthi Seelam、Sampath Kumar Halmuthur. M.

  DOI：10.1080/00397911.2023.2196024

  日期：2023.5.19

  convergent strategy, where mitsunobu reaction was conducted to synthesize the common starting material. The novel analogues displayed immunomodulatory potential as indicated by the anti-inflammatory effect derived through the compound’s T cell proliferation inhibitory property. The synthesized novel analogues manifested encouraging biological responses, assure their application as immunomodulators.

  摘要 免疫调节剂被指定为治疗各种疾病（如艾滋病、癌症和自身免疫性疾病）的有力工具。在这项工作中，我们合成了一系列基于氟西汀的小分子免疫调节剂。通过收敛策略合成分子，其中进行 mitsunobu 反应以合成共同的起始材料。新型类似物显示出免疫调节潜力，正如化合物的 T 细胞增殖抑制特性所产生的抗炎作用所表明的那样。合成的新型类似物表现出令人鼓舞的生物反应，确保它们作为免疫调节剂的应用。
• Antiplasmodial activity of new 4-aminoquinoline derivatives against chloroquine resistant strain
  作者：Manish Sinha、Vasanth R. Dola、Pooja Agarwal、Kumkum Srivastava、Wahajul Haq、Sunil K. Puri、Seturam B. Katti

  DOI：10.1016/j.bmc.2014.05.024

  日期：2014.7

  Emergence and spread of multidrug resistant strains of Plasmodium falciparum has severely limited the antimalarial chemotherapeutic options. In order to overcome the obstacle, a set of new side-chain modified 4-aminoquinolines were synthesized and screened against chloroquine-sensitive (3D7) and chloroquine-resistant (K1) strains of P. falciparum. The key feature of the designed molecules is the use of methylpiperazine linked α, β(3)- and γ-amino acids to generate novel side chain modified 4-aminoquinoline analogues. Among the evaluated compounds, 20c and 30 were found more potent than CQ against K1 and displayed a four-fold and a three-fold higher activity respectively, with a good selectivity index (SI=5846 and 11,350). All synthesized compounds had resistance index between 1.06 and >14.13 as against 47.2 for chloroquine. Biophysical studies suggested that this series of compounds act on heme polymerization target.