Wieland T, Miura T, Seeliger A
Int J Pept Protein Res. 1983 Jan;21(1):3-10.
The analogs [D-Abu2-Lys7]-phalloin (1) and [D-Ala2-Leu7]-phalloin (2) are obtained by cyclization of the monocyclic thioether peptides 5 and 7 with DCCI and diphenylphosphoro-azidate respectively. For the synthesis of 5 and 7 an intramolecular Savige-Fontana reaction of the linear heptapeptide tert.-butylesters 4 and 6 is applied. On treatment in dilute solution with TFA the classically synthesized peptides 4 and 6 lose their N-terminal Boc groups thus giving rise to the reaction of the Hpi residues with the released cysteine SH-groups. The lysine analog 1 binds to F-actin with an association constant of 1.3 X 10(-6) M whereas analog 2 exhibits practically no affinity. By reaction of 1 with tetramethyl-rhodaminyl-isothiocyanate a fluorescent derivative, rhodaminyl-lysine-phallotoxin (RLP), is obtained as a novel fluorescent probe for the visualization of F-actin in cell preparations.
类似物[D- Abu2-Lys7]-鬼笔环肽（1）和[D- Ala2-Leu7]-鬼笔环肽（2）分别通过二环己基碳二亚胺（DCCI）和二苯基磷酰叠氮化物使单环硫醚肽5和7环化得到。为了合成5和7，应用了线性七肽叔丁酯4和6的分子内萨维奇-丰塔纳反应。在用三氟乙酸（TFA）稀溶液处理时，经典合成的肽4和6失去其N端的叔丁氧羰基（Boc）基团，从而导致羟脯氨酸（Hpi）残基与释放的半胱氨酸巯基发生反应。赖氨酸类似物1以1.3×10⁻⁶ M的缔合常数与F-肌动蛋白结合，而类似物2几乎没有亲和力。通过1与四甲基罗丹明异硫氰酸酯反应，得到一种荧光衍生物罗丹明-赖氨酸-鬼笔毒素（RLP），作为一种用于在细胞制剂中可视化F-肌动蛋白的新型荧光探针。
