homoserine lactone trifluoroacetate salt | 77856-40-7

• 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: homoserine lactone trifluoroacetate salt
• 英文别名: (S)-2-oxotetrahydrofuran-3-aminium trifluoroacetate；L-homoserine lactone trifluoroacetate；homoserine lactone mono-trifluoroacetate
• CAS: 77856-40-7
• 化学式: C₂HF₃O₂*C₄H₇NO₂
• 分子量: 215.129
• InChiKey: UCYVKTWSVHLLRA-DFWYDOINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.11
• 重原子数：
  14.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  89.62
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  BOC-L-脯氨酸 、 homoserine lactone trifluoroacetate salt 在 N-甲基吗啉 、 氯甲酸乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 0.37h， 以70%的产率得到(S)-tert-butyl 2-(((S)-2-oxotetrahydrofuran-3-yl)carbamoyl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Solution structural features of N -acyl homoserine lactones

  摘要：

  Here we demonstrate that in interbacterial quorum signal moderators, N-acylhomoserine lactones (AHLs), the stabilization of bioactive pharmacophore lactone against lysis is through the e(-) withdrawing N-acyl motif which reduces lactone carbonyl polarization. This lysis is assisted by weak (<0.05 kcal mol(-1)) contacts between N-acyl O and lactone C'. The interactions that preclude this weak contact, in the free and receptor-bound AHLs, improve lactone halflife and hence are key to the design of the antibacterial AHL analogues. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.08.078
• 作为产物：
  描述：

  L-高丝氨酸 、 三氟乙酸 反应 48.0h， 生成 homoserine lactone trifluoroacetate salt
  参考文献：
  名称：

  Total synthesis of 2'-deoxymugineic acid, the metal chelator excreted from wheat root

  摘要：

  DOI：

  10.1021/ja00399a046

文献信息

• Derivatives of syringolin A
  申请人：Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V.

  公开号：EP2210881A1

  公开（公告）日：2010-07-28

  The present invention relates to syringolin A derivatives, the use of the syringolin A derivatives for prophylaxis and treatment of neurodegenerative diseases and proliferative diseases such as cancer, pharmaceutical compositions containing at least one syringolin A derivative as well as to a synthesis for preparing the syringolin A derivatives.

  本发明涉及丝菌素A衍生物，使用丝菌素A衍生物预防和治疗神经退行性疾病和增殖性疾病，如癌症，含有至少一种丝菌素A衍生物的药物组合物，以及制备丝菌素A衍生物的合成方法。
• A Convenient Synthesis of L-α-Vinylglycine from L-Homoserine Lactone
  作者：David B. Berkowitz、Marianne K. Smith

  DOI：10.1055/s-1996-4177

  日期：1996.1

  A procedure for the synthesis of L-α-vinylglycine from L-homoserine lactone is described. The route developed is convenient (only one chromatography step is required) and efficient (71%; ≥ 95% optical yield over 4 steps). Key features include the use of acid-labile protecting groups for the amino (Bod) and carboxyl (diphenylmethyl ester) groups, and the use of the phenylselenolate equivalent derived from sodium borohydride and diphenyl diselenide for L-homoserine lactone cleavage.

  描述了从 L-高丝氨酸内酯合成 L-α-乙烯基甘氨酸的程序。所开发的路线方便（仅需要一个色谱步骤）且高效（71%；4 个步骤光学产率≥ 95%）。主要特点包括对氨基 (Bod) 和羧基（二苯基甲酯）基团使用酸不稳定保护基团，以及使用源自硼氢化钠和二苯基二硒化物的苯基硒酸盐等价物进行 L-高丝氨酸内酯裂解。
• SYNTHESIS OF (+)-AVENIC ACID A
  作者：Yasufumi Ohfune、Kyosuke Nomoto

  DOI：10.1246/cl.1981.827

  日期：1981.6.5

  Avenic acid A (2), the metal chelator excreted from oat root and the factor which is considered to be directly involved in the uptake and transport of iron and other elements, has been synthesized efficiently from L-N[3-hydroxy-3-carboxypropyl]homoserine aldehyde, which could be a biosynthetic precursor.

  燕麦酸A(2)是燕麦根分泌的金属螯合剂，被认为是直接参与铁等元素吸收和转运的因子，由LN[3-羟基-3-羧丙基]高效合成高丝氨酸醛，它可能是一种生物合成前体。