pagoamide A

• 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: pagoamide A
• 英文别名: N-[(2R)-1-[[(3S,6S,9R,12R,15S,18S,19R)-3,9-dibenzyl-15-(hydroxymethyl)-12,19-dimethyl-2,5,8,11,14,17-hexaoxo-6-propan-2-yl-1-oxa-4,7,10,13,16-pentazacyclononadec-18-yl]amino]-3-hydroxy-1-oxopropan-2-yl]-2-[[[2-[(1S)-1-(dimethylamino)-2-methylpropyl]-1,3-thiazole-4-carbonyl]amino]methyl]-1,3-thiazole-4-carboxamide
• 化学式: C₅₁H₆₇N₁₁O₁₂S₂
• 分子量: 1090.29
• InChiKey: DGNIWMWQQSOCJM-SVWUPQTBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.11
• 重原子数：
  76.0
• 可旋转键数：
  17.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  328.58
• 氢给体数：
  10.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  pagoamide A 在 盐酸 作用下， 以 水 为溶剂， 反应 16.0h， 生成 D-丙氨酸 、 L-缬氨酸 、 D-丝氨酸 、 L-丝氨酸 、 L-苏氨酸 、 L-苯丙氨酸 、 D-苯丙氨酸 、 、 2-(氨基甲基)-1,3-噻唑-4-羧酸
  参考文献：
  名称：

  Pagoamide A, a Cyclic Depsipeptide Isolated from a Cultured Marine Chlorophyte, Derbesia sp., Using MS/MS-Based Molecular Networking

  摘要：

  A thiazole-containing cyclic depsipeptide with 11 amino acid residues, named pagoamide A (1), was isolated from laboratory cultures of a marine Chlorophyte, Derbesia sp. This green algal sample was collected from America Samoa, and pagoamide A was isolated using guidance by MS/MS-based molecular networking. Cultures were grown in a light- and temperature-controlled environment and harvested after several months of growth. The planar structure of pagoamide A (1) was characterized by detailed 1D and 2D NMR experiments along with MS and UV analysis. The absolute configurations of its amino acid residues were determined by advanced Marfey's analysis following chemical hydrolysis and hydrazinolysis reactions. Two of the residues in pagoamide A (1), phenylalanine and serine, each occurred twice in the molecule, once in the D- and once in the L-configuration. The biosynthetic origin of pagoamide A (1) was considered in light of other natural products investigations with coenocytic green algae.

  DOI：

  10.1021/acs.jnatprod.9b01019

文献信息

• Pagoamide A, a Cyclic Depsipeptide Isolated from a Cultured Marine Chlorophyte, <i>Derbesia</i> sp., Using MS/MS-Based Molecular Networking
  作者：Yueying Li、Hao-Bing Yu、Yi Zhang、Tiago Leao、Evgenia Glukhov、Marsha L. Pierce、Chen Zhang、Hyunwoo Kim、Huanru Henry Mao、Fang Fang、Garrison W. Cottrell、Thomas F. Murray、Lena Gerwick、Huashi Guan、William H. Gerwick

  DOI：10.1021/acs.jnatprod.9b01019

  日期：2020.3.27

  A thiazole-containing cyclic depsipeptide with 11 amino acid residues, named pagoamide A (1), was isolated from laboratory cultures of a marine Chlorophyte, Derbesia sp. This green algal sample was collected from America Samoa, and pagoamide A was isolated using guidance by MS/MS-based molecular networking. Cultures were grown in a light- and temperature-controlled environment and harvested after several months of growth. The planar structure of pagoamide A (1) was characterized by detailed 1D and 2D NMR experiments along with MS and UV analysis. The absolute configurations of its amino acid residues were determined by advanced Marfey's analysis following chemical hydrolysis and hydrazinolysis reactions. Two of the residues in pagoamide A (1), phenylalanine and serine, each occurred twice in the molecule, once in the D- and once in the L-configuration. The biosynthetic origin of pagoamide A (1) was considered in light of other natural products investigations with coenocytic green algae.