(2S,4S)-2,4-dimethylheptanoic acid

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S,4S)-2,4-dimethylheptanoic acid
• 化学式: C₉H₁₈O₂
• 分子量: 158.241
• InChiKey: PLTFCXPZUBKUMW-YUMQZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-(+)-2-苯甘氨酸甲酯 盐酸盐 、 (2S,4S)-2,4-dimethylheptanoic acid 在 N-羟基-7-氮杂苯并三氮唑 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.5h， 以51%的产率得到methyl (S)-2-((2S,4S)-2,4-dimethylheptanamido)-2-phenylacetate
  参考文献：
  名称：

  Tumescenamide C, an antimicrobial cyclic lipodepsipeptide from Streptomyces sp.

  摘要：

  Tumescenamide C, a new cyclic lipodepsipeptide, was isolated from a culture broth of an actinomycete Streptomyces sp. KUSC_F05. Tumescenamide C was a congener of tumescenamides A and B, representing a sixteen-membered ring system, consisting of two proteinogenic and three non-proteinogenic amino acids, to which a methyl-branched fatty acid was attached. The planar structure was determined by spectroscopic analysis, while its absolute stereochemistry was determined by chemical degradation and asymmetric synthesis. Tumescenamide C exhibited antimicrobial activity with high selectivity against Streptomyces species. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.04.075
• 作为产物：
  描述：

  2-甲基-1-戊醇 在 吡啶 、 lithium hydroxide monohydrate 、 双氧水 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 6.33h， 生成 (2S,4S)-2,4-dimethylheptanoic acid
  参考文献：
  名称：

  Tumescenamide C, an antimicrobial cyclic lipodepsipeptide from Streptomyces sp.

  摘要：

  Tumescenamide C, a new cyclic lipodepsipeptide, was isolated from a culture broth of an actinomycete Streptomyces sp. KUSC_F05. Tumescenamide C was a congener of tumescenamides A and B, representing a sixteen-membered ring system, consisting of two proteinogenic and three non-proteinogenic amino acids, to which a methyl-branched fatty acid was attached. The planar structure was determined by spectroscopic analysis, while its absolute stereochemistry was determined by chemical degradation and asymmetric synthesis. Tumescenamide C exhibited antimicrobial activity with high selectivity against Streptomyces species. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.04.075

文献信息

• Total Synthesis and Antimicrobial Activity of Tumescenamide C and Its Derivatives
  作者：Nobuaki Takahashi、Kensuke Kaneko、Hideaki Kakeya

  DOI：10.1021/acs.joc.9b03516

  日期：2020.3.20

  C (1) is an antimicrobial compound produced by Streptomyces sp. KUSC_F05 and consists of a cyclic depsipeptide core and a polyketide side chain with branched methyl groups. Here, we report the total synthesis of tumescenamide C and two derivatives, mainly using Fmoc solid-phase peptide synthesis (SPPS). In addition, a biological evaluation of these compounds revealed the critical partial structure

  Tumescenamide C（1）是由链霉菌属（Streptomyces sp。）生产的一种抗菌化合物。KUSC_F05由环状二肽核心和带有分支甲基的聚酮侧链组成。在这里，我们报告了图梅净胺C和两种衍生物的总合成，主要使用Fmoc固相肽合成（SPPS）。此外，对这些化合物的生物学评估显示出抗菌活性中关键的部分结构。
• Antibiotics from the marine pulmonate siphonaria diemenensis
  作者：Jill E. Hochlowski、D.John Faulkner

  DOI：10.1016/s0040-4039(00)81805-5

  日期：1983.1

  The marine pulmonate Siphonaria diemenensis collected intertidally in southeastern Australia, contained two polypropionate antibiotics diemenensin-A (1) and diemenensin-B (2). The structures were elucidated through interpretation of spectral data and by degradation.

  在澳大利亚东南部陆续收集的海生肺孢子虫Siphonaria diemenensis，包含两种聚丙烯酸酯抗生素diemenensin-A（1）和diemenensin-B（2）。通过解释光谱数据和降解来阐明结构。
• Tumescenamide C, an antimicrobial cyclic lipodepsipeptide from Streptomyces sp.
  作者：Shinji Kishimoto、Yuta Tsunematsu、Shinichi Nishimura、Yutaka Hayashi、Akira Hattori、Hideaki Kakeya

  DOI：10.1016/j.tet.2012.04.075

  日期：2012.7

  Tumescenamide C, a new cyclic lipodepsipeptide, was isolated from a culture broth of an actinomycete Streptomyces sp. KUSC_F05. Tumescenamide C was a congener of tumescenamides A and B, representing a sixteen-membered ring system, consisting of two proteinogenic and three non-proteinogenic amino acids, to which a methyl-branched fatty acid was attached. The planar structure was determined by spectroscopic analysis, while its absolute stereochemistry was determined by chemical degradation and asymmetric synthesis. Tumescenamide C exhibited antimicrobial activity with high selectivity against Streptomyces species. (c) 2012 Elsevier Ltd. All rights reserved.