Martin C, Oberer L, Ino T, König W A, Busch M, Weckesser J
Institut für Biologie II, Albert-Ludwigs-Universität, Freiburg, F.R.G.
J Antibiot (Tokyo). 1993 Oct;46(10):1550-6. doi: 10.7164/antibiotics.46.1550.
Four depsipeptides (peptide lactones), called cyanopeptolins A, B, C and D, have been isolated from the cyanobacterium Microcystis sp. PCC 7806. They possess identical structures consisting of cyclic L-glutamic acid-gamma-aldehyde, L-leucine, N-methyl-phenylalanine, L-valine, L-threonine, L-aspartic acid, hexanoic acid and a variable basic amino acid. This variable amino acid can be L-arginine (cyanopeptolin A), L-lysine (cyanopeptolin B), N epsilon-methyl-L-lysine (cyanopeptolin C) and N epsilon,N epsilon-dimethyl-L-lysine (cyanopeptolin D), respectively. The L-glutamic acid-gamma-aldehyde and the amino group of L-leucine form an unusual 3-amino-6-hydroxy-2-oxo-1-piperidine system. L-Threonine is connected to L-valine via its hydroxy-group forming an ester bonding. The hexanoic acid residue is attached to the N-terminal aspartic acid residue which is not a part of the ring structure. The isolation procedure of the four cyanopeptolins as well as structure elucidation are described. Amino acid analysis, GC/MS analysis, FAB-MS and several NMR techniques were used to reveal the structures.
从蓝藻微囊藻属PCC 7806中分离出了四种缩肽（肽内酯），分别称为蓝藻肽毒素A、B、C和D。它们具有相同的结构，由环状L-谷氨酸-γ-醛、L-亮氨酸、N-甲基苯丙氨酸、L-缬氨酸、L-苏氨酸、L-天冬氨酸、己酸和一种可变的碱性氨基酸组成。这种可变氨基酸分别可以是L-精氨酸（蓝藻肽毒素A）、L-赖氨酸（蓝藻肽毒素B）、Nε-甲基-L-赖氨酸（蓝藻肽毒素C）和Nε,Nε-二甲基-L-赖氨酸（蓝藻肽毒素D）。L-谷氨酸-γ-醛和L-亮氨酸的氨基形成了一个不寻常的3-氨基-6-羟基-2-氧代-1-哌啶系统。L-苏氨酸通过其羟基与L-缬氨酸相连，形成酯键。己酸残基连接到N端的天冬氨酸残基上，该残基不是环结构的一部分。描述了四种蓝藻肽毒素的分离过程以及结构解析。使用氨基酸分析、气相色谱/质谱分析、快原子轰击质谱和几种核磁共振技术来揭示其结构。
