H₂N-(R)-γ⁴-Leu-OMe | 724418-57-9

• 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: H₂N-(R)-γ⁴-Leu-OMe
• 英文别名: methyl (4R)-4-amino-6-methylheptanoate
• CAS: 724418-57-9
• 化学式: C₉H₁₉NO₂
• 分子量: 173.255
• InChiKey: AMGQGJGJUOYNOE-MRVPVSSYSA-N

物化性质

• 沸点：
  231.0±23.0 °C(Predicted)
• 密度：
  0.936±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  H₂N-(R)-γ⁴-Leu-OMe 在 盐酸 作用下， 生成 (4R)-4-amino-6-methylheptanoic acid
  参考文献：
  名称：

  手性溶质-溶剂系统。N-十二烷酰基-L-缬氨酸酰胺与2-氨基烷-1-醇对映体的N-三氟乙酰基酯与α-，β-和γ-氨基酸之间的选择性相互作用

  摘要：

  以O-酰基-N-三氟乙酰基衍生物形式存在的旋光2-氨基烷-1-醇已通过使用N-十二烷酰基-L-缬氨酸6-十一烷基酰胺（1）作为固定相的glc拆分。庞大的O-酰基基团大大促进了拆分。还报道了二酰胺相上α-，β-和γ-氨基酸的N-三氟乙酰基酯的拆分。在L-异构体之后，2-氨基烷-1-醇和γ-氨基酸的衍生物的出现顺序为D，即与α-氨基酸相反。

  DOI：

  10.1039/p29790001230
• 作为产物：
  描述：

  2-甲基-2-丙基[(2S)-4-甲基-1-氧代-2-戊烷基]氨基甲酸酯 在 palladium on activated charcoal 氢气 、 三氟乙酸 作用下， 以 甲醇 为溶剂， 生成 H₂N-(R)-γ⁴-Leu-OMe
  参考文献：
  名称：

  1,3-Asymmetric induction in enolate alkylation reactions of N-protected γ-amino acid derivatives

  摘要：

  Dianions derived from N-TFA and N-Boc gamma-amino acid esters and amides undergo highly stereoselective alpha-alkylation reactions The roles of HMPA, of the cation, the electrophile, and of steric factors were studied. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0040-4039(96)02263-0

文献信息

• An α-Helix-Mimicking 12,13-Helix: Designed α/β/γ-Foldamers as Selective Inhibitors of Protein-Protein Interactions
  作者：Claire M. Grison、Jennifer A. Miles、Sylvie Robin、Andrew J. Wilson、David J. Aitken

  DOI：10.1002/anie.201604517

  日期：2016.9.5

  interactions (PPIs). In this work, trans‐2‐aminocyclobutanecarboxylic acid (tACBC) was used as the key β‐amino acid component in the design of α/β/γ‐peptides to structurally mimic a native α‐helix. Suitably functionalized α/β/γ‐peptides assume an α‐helix‐mimicking 12,13‐helix conformation in solution, exhibit enhanced proteolytic stability in comparison to the wild‐type α‐peptide parent sequence from which

  当前生物有机化学的一个主要挑战是鉴定蛋白质二级结构的有效模拟物，作为蛋白质-蛋白质相互作用（PPI）的抑制剂。在这项工作中，反式-2-氨基环丁烷甲酸（ t ACBC）被用作α/β/ γ-肽设计中的关键β-氨基酸成分，以在结构上模拟天然的α-螺旋。适当功能化的 α/β/γ-肽在溶液中呈现模拟 12,13-螺旋构象的 α-螺旋，与衍生它们的野生型 α-肽亲本序列相比，表现出增强的蛋白水解稳定性，并充当p53/ h DM2 相互作用的选择性抑制剂。
• Phospholipase A2 Inhibitors and their Use in Treating Neurological Injury and Disease
  申请人：Dennis Edward A.

  公开号：US20110105610A1

  公开（公告）日：2011-05-05

  Phospholipase A 2 (PLA 2 ) forms are expressed in spinal cord whose inhibition induces a potent antihyperalgesia. PLA 2 inhibitor compounds are provided that include a common motif consisting of a 2-oxoamide with a hydrocarbon tail and a four carbon tether. The compounds block Group IVA calcium dependent PLA 2 (cPLA 2 ) and/or Group VIA calcium independent PLA 2 (iPLA 2 ) and/or Group V secreted PLA 2 (sPLA 2 ). Pharmaceutical compositions of compounds having cPLA 2 inhibitory activity (but not iPLA 2 or sPLA 2 inhibitory activity) are useful in treating multiple sclerosis, while compositions of compounds having sPLA 2 inhibitory activity (as well as iPLA 2 and CPLA 2 activity) are useful in treating spinal cord injuries (with related functional recovery).
• US8420852B2
  申请人：——

  公开号：US8420852B2

  公开（公告）日：2013-04-16
• [EN] PHOSPHOLIPASE A2 INHIBITORS AND THEIR USE IN TREATING NEUROLOGICAL INJURY AND DISEASE<br/>[FR] INHIBITEURS DE PHOSPHOLIPASES A2 ET LEUR UTILISATION POUR TRAITER LES LÉSIONS ET LES MALADIES NEUROLOGIQUES
  申请人：UNIV CALIFORNIA

  公开号：WO2009009449A2

  公开（公告）日：2009-01-15

  Phospholipase A2 (PLA2) forms are expressed in spinal cord whose inhibition induces a potent antihyperalgesia. PLA2 inhibitor compounds are provided that include a common motif consisting of a 2-oxoamide with a hydrocarbon tail and a four carbon tether. The compounds block Group IVA calcium dependent PLA2 (cPLA2) and/or Group VIA calcium independent PLA2 (iPLA2) and/or Group V secreted PLA2 (sPLA2). Pharmaceutical compositions of compounds having cPLA2 inhibitory activity (but not iPLA2 or sPLA2 inhibitory activity) are useful in treating multiple sclerosis, while compositions of compounds having sPLA2 inhibitory activity (as well as iPLA2 and CPLA2 activity) are useful in treating spinal cord injuries (with related functional recovery).
• 1,3-Asymmetric induction in enolate alkylation reactions of N-protected γ-amino acid derivatives
  作者：Stephen Hanessian、Robert Schaum

  DOI：10.1016/s0040-4039(96)02263-0

  日期：1997.1

  Dianions derived from N-TFA and N-Boc gamma-amino acid esters and amides undergo highly stereoselective alpha-alkylation reactions The roles of HMPA, of the cation, the electrophile, and of steric factors were studied. Copyright (C) 1996 Elsevier Science Ltd