pholipeptin

• 分子结构分类: 有机化合物 - 有机聚合物 - 多肽
• 英文名称: pholipeptin
• 英文别名: (4R,7S,10R,13R,16R,19R,22R,25R,28S,29R)-7-butan-2-yl-28-[[(2S)-3-carboxy-2-[[(2R)-2-(3-hydroxydecanoylamino)-4-methylpentanoyl]amino]propanoyl]amino]-13,19-bis(hydroxymethyl)-29-methyl-10,16,22,25-tetrakis(2-methylpropyl)-2,6,9,12,15,18,21,24,27-nonaoxo-1-oxa-5,8,11,14,17,20,23,26-octazacyclononacosane-4-carboxylic acid
• 化学式: C₆₄H₁₁₁N₁₁O₂₀
• 分子量: 1354.65
• InChiKey: FIDWFJZZQLPPLI-VHCKHPADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  95
• 可旋转键数：
  30
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  482
• 氢给体数：
  16
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  pholipeptin 在 盐酸 作用下， 反应 20.0h， 生成 D-丝氨酸 、 L-苏氨酸 、 D-亮氨酸 、 L-异亮氨酸 、 D-天门冬氨酸 、 L-天门冬氨酸
  参考文献：
  名称：

  Pholipeptin, a Novel Cyclic Lipoundecapeptide from Pseudomonas fluorescens

  摘要：

  An inhibitor of phosphatidylinositol-specific phospholipase C (PI-PLC), pholipeptin (1), was purified from the culture broth of Pseudomonas sp. by solvent extraction and column chromatography. Acid hydrolysis of 1 gave Leu, Ile, Ser, Thr, and Asp moieties. Although 1 was a peptide compound, fragmentation by mild hydrolysis was not accomplished under any conditions. So, we performed the structure elucidation using various 2D NMR techniques. In the NMR studies, the addition of a small amount of trifluoroacetic acid gave relatively sharp and resolved signals, such that the structure of this novel cyclic lipodepsipeptide consisting of 11 amino acids and a 3-hydroxydecanoic acid moiety could be determined. Chirality of the constituent amino acids was analyzed by chiral HPLC, but two Asp residues could not be distinguished because they were contained as a racemic mixture. Finally, their chiralities were determined by NMR analysis of C-13-labeled 1 into which [L-C-13]Asp had been biosynthetically incorporated.

  DOI：

  10.1021/jo9603993

文献信息

• Pholipeptin, a Novel Cyclic Lipoundecapeptide from<i> Pseudomonas fluorescens</i>
  作者：Hideaki Ui、Toshiaki Miyake、Hironobu Iinuma、Masaya Imoto、Hiroshi Naganawa、Seiko Hattori、Masa Hamada、Tomio Takeuchi、Sumio Umezawa、Kazuo Umezawa

  DOI：10.1021/jo9603993

  日期：1997.1.1

  An inhibitor of phosphatidylinositol-specific phospholipase C (PI-PLC), pholipeptin (1), was purified from the culture broth of Pseudomonas sp. by solvent extraction and column chromatography. Acid hydrolysis of 1 gave Leu, Ile, Ser, Thr, and Asp moieties. Although 1 was a peptide compound, fragmentation by mild hydrolysis was not accomplished under any conditions. So, we performed the structure elucidation using various 2D NMR techniques. In the NMR studies, the addition of a small amount of trifluoroacetic acid gave relatively sharp and resolved signals, such that the structure of this novel cyclic lipodepsipeptide consisting of 11 amino acids and a 3-hydroxydecanoic acid moiety could be determined. Chirality of the constituent amino acids was analyzed by chiral HPLC, but two Asp residues could not be distinguished because they were contained as a racemic mixture. Finally, their chiralities were determined by NMR analysis of C-13-labeled 1 into which [L-C-13]Asp had been biosynthetically incorporated.