papuamide 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: papuamide A
• 英文别名: (2R,3S,4S)-4-[[(2S,3S)-3-amino-2-[[(2R,3R)-2-[[2-[[(4Z,6E)-2,3-dihydroxy-2,6,8-trimethyldeca-4,6-dienoyl]amino]acetyl]amino]-3-hydroxybutanoyl]amino]butanoyl]amino]-N'-[(6R,9S,15R,18R,19R,22S)-6-[(1R)-1-hydroxyethyl]-3-[(4-hydroxyphenyl)-methoxymethyl]-15-(methoxymethyl)-7,9-dimethyl-2,5,8,11,14,17,21-heptaoxo-19-propan-2-yl-20-oxa-1,4,7,10,13,16-hexazabicyclo[20.4.0]hexacosan-18-yl]-2,3-dimethylpentanediamide
• 化学式: C₆₆H₁₀₅N₁₃O₂₁
• 分子量: 1416.63
• InChiKey: MKAKHXFSEWECNW-MGGNZISXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  100
• 可旋转键数：
  27
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  518
• 氢给体数：
  16
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  papuamide A 、 碘甲烷 在 potassium carbonate 作用下， 生成 papuamide C
  参考文献：
  名称：

  Papuamides A−D, HIV-Inhibitory and Cytotoxic Depsipeptides from the Sponges Theonella mirabilis and Theonella swinhoei Collected in Papua New Guinea

  摘要：

  The novel cyclic depsipeptides papuamides A (1), B (2), C (3), and D (4) have been isolated from Papua New Guinea collections of the sponges Theonella mirabilis and Theonella swinhoei. Their structures were determined by a combination of spectroscopic analysis and chemical degradation and derivatization studies. In addition to glycine, alanine, and threonine, these peptides contain a number of unusual amino acids including 3,4-dimethylglutamine, beta-methoxytyrosine, 3-methoxyalanine, and 2,3-diaminobutanoic acid or 2-amino-2-butenoic acid residues. Papuamides A-D (1-4) are also the first marine-derived peptides reported to contain 3-hydroxyleucine and homoproline residues. These peptides also contain a previously undescribed 2,3-dihydroxy-2,6,8-trimethyldeca-(4Z,6E)-dienoic acid moiety N-linked to a terminal glycine residue. Papuamides A (1) and B (2) inhibited the infection of human T-lymphoblastoid cells by HIV-1(RF) in vitro with an EC50 of approximately 4 ng/mL. Compound 1 was also cytotoxic against a panel of human cancer cell lines with a mean IC50 of 75 ng/mL.

  DOI：

  10.1021/ja990582o