tumescenamide C | 1383580-56-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: tumescenamide C
• 英文别名: (2S,4S)-N-((6R,9R,12S,15S,16R,Z)-3-ethylidene-6-(4-hydroxybenzyl)-12-isobutyl-9-isopropyl-16-methyl-2,5,8,11,14-pentaoxo-1-oxa-4,7,10,13-tetraazacyclohexadecan-15-yl)-2,4-dimethylheptanamide；(2S,4S)-N-[(3Z,6R,9R,12S,15S,16R)-3-ethylidene-6-[(4-hydroxyphenyl)methyl]-16-methyl-12-(2-methylpropyl)-2,5,8,11,14-pentaoxo-9-propan-2-yl-1-oxa-4,7,10,13-tetrazacyclohexadec-15-yl]-2,4-dimethylheptanamide
• CAS: 1383580-56-0
• 化学式: C₃₇H₅₇N₅O₈
• 分子量: 699.888
• InChiKey: CUJBKWCXRLZJMY-AVQLBBDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  50
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  192
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tumescenamide C 在 盐酸 、 N-羟基-7-氮杂苯并三氮唑 、 水 、 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 41.0h， 生成 methyl (R)-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：

  在 甲基磺酰氯 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 17.5h， 生成 tumescenamide C
  参考文献：
  名称：

  土磺酰胺C及其衍生物的总合成及其抗菌活性。

  摘要：

  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。

  DOI：

  10.1021/acs.joc.9b03516

文献信息

• 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.
• 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。