variochelin A

• 分子结构分类: 有机化合物 - 有机聚合物 - 多肽
• 英文名称: variochelin A
• 英文别名: (2S)-5-[acetyl(hydroxy)amino]-2-[[(2S)-5-[acetyl(hydroxy)amino]-2-[[(2S)-1-[(2R)-2-[[(2S,3S)-3-carboxy-2-[[(2S,3S,4S)-7-(diaminomethylideneamino)-4-(dodecanoylamino)-3-hydroxy-2-methylheptanoyl]amino]-3-hydroxypropanoyl]amino]-3-hydroxypropanoyl]pyrrolidine-2-carbonyl]amino]pentanoyl]amino]pentanoic acid
• 化学式: C₄₇H₈₃N₁₁O₁₇
• 分子量: 1074.24
• InChiKey: GRFONBIZQKDBOK-GVMUGWJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.86
• 重原子数：
  75.0
• 可旋转键数：
  38.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  444.08
• 氢给体数：
  15.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  (1R,2S,5R)-Menthyl chloroformate 、 variochelin A 在 水 、 氢碘酸 、 碳酸氢钠 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 9.0h， 生成
  参考文献：
  名称：

  Variochelins, Lipopeptide Siderophores from Variovorax boronicumulans Discovered by Genome Mining

  摘要：

  Photoreactive siderophores have a major impact on the. growth of planktonic organisms. To date, these molecules have mainly been reported from marine bacteria, although evidence is now accumulating that some terrestrial bacteria also harbor the biosynthetic potential for their production. In this paper, we describe the genomics-driven discovery and characterization of variochelins, lipopeptide siderophores from the bacterium Variovorax boronicumulans, which thrives in soil and freshwater habitats. Variochelins are different from most other lipopeptide siderophores in that their biosynthesis involves a polyketide synthase. We demonstrate that the ferric iron complex of variochelin A possesses photoreactive properties and present the MS-derived structures of two degradation products that emerge upon light exposure.

  DOI：

  10.1021/acs.jnatprod.5b00932

文献信息

• New variochelins from soil-isolated Variovorax sp. H002
  作者：Jabal Rahmat Haedar、Aya Yoshimura、Toshiyuki Wakimoto

  DOI：10.3762/bjoc.20.63

  日期：——

  The soil bacterial genus Variovorax produce distinct photoreactive siderophores that may play a crucial role in the iron cycle within the rhizosphere. This study focused on exploring the natural products of the soil-isolated Variovorax sp. H002, leading to the isolation of variochelins A–E (1–5), a series of lipohexapeptide siderophores. NMR and MS/MS analyses revealed that these siderophores share a common core structure – a linear hexapeptide with β-hydroxyaspartate and hydroxamate functional groups, serving in iron-binding coordination. Three new variochelins C–E (3–5) were characterized by varied fatty acyl groups at their N-termini; notably, 4 and 5 represent the first variochelins with N-terminal unsaturated fatty acyl groups. Furthermore, the variochelin biosynthetic gene cluster was identified through draft genome sequencing and gene knockout experiments. Compounds 1–5 exhibited antimicrobial activities against Gram-negative bacteria, including several soil-isolated plant pathogens.