7>Microcystin-LR

• 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: 7>Microcystin-LR
• 英文别名: (L-MeLan7)-Microcystin-LR；(2R,5R,8S,12S,15S,19S,22R)-2-[[(2R)-2-amino-2-carboxyethyl]sulfanylmethyl]-15-[3-(diaminomethylideneamino)propyl]-18-[(1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dienyl]-1,5,12,19-tetramethyl-8-(2-methylpropyl)-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptazacyclopentacosane-11,22-dicarboxylic acid
• 化学式: C₅₂H₈₁N₁₁O₁₄S
• 分子量: 1116.35
• InChiKey: VXYRNKOTKQZSDD-ILPBAUAISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  78
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  432
• 氢给体数：
  12
• 氢受体数：
  17

反应信息

• 作为产物：
  描述：

  L-半胱氨酸盐酸盐无水物 、 Microcystin-LR 在 碳酸氢钠 作用下， 以 水 为溶剂， 反应 18.0h， 生成 7>Microcystin-LR
  参考文献：
  名称：

  Seven More Microcystins from Homer Lake Cells: Application of the General Method for Structure Assignment of Peptides Containing .alpha.,.beta.-Dehydroamino Acid Unit(s)

  摘要：

  Larger scale isolation of microcystins, cyclic heptapeptide hepatotoxins, from a water bloom of Microcystis spp. collected from Homer Lake (Illinois) gave the previously reported 1-5, additional quantities of [L-MeSer(7)]microcystin-LR (6), and microcystin-(H-4)YR [8, (H-4)Y = 1',2',3',4'-tetrahydrotyrosine], which were previously isolated in insufficient amounts to complete the structure assignment, and seven more microcystins, 9-15. A general method for assigning the structures of cyclic peptides containing alpha,beta-unsaturated amino acid unit(s) developed with nodularin, a cyclic pentapeptide hepatotoxin, was applied to confirm the previously assigned structures of 1-5 and to assign the structures of [D-Asp(3)]microcystin-LR (9) and the. new microcystin-HilR (10, Hil = homoisoleucine). The method consists of linearization of a cyclic molecule by a one-pot reaction sequence (ozonolysis followed by NaBH4 reduction) and tandem FARMS (FABMS/CID/MS) analysis of the product (linear peptide). A new microcystin, 11, was assigned the structure [L-MeLan(7)]microcystin-LR (MeLan = N-methyllanthionine) and synthesized from 1 and L-Cys. Four linear peptides 12-15, which are reasonable biogenetic precursors of the cyclic compounds, were also assigned structures based on their FABMS/CID/MS data.

  DOI：

  10.1021/jo00117a017