Mihara H, Aoyagi H, Yonezawa H, Kuromizu K, Izumiya N
Int J Pept Protein Res. 1985 Jun;25(6):640-7.
K-582 A, an antibiotic heptapeptide, has a sequence of H-L-Arg-L-Arg(OH)-D-Orn-L-Thr-D-Orn-L-Lys-D-Tyr-OH (Arg(OH), threo-gamma-hydroxyarginine). In order to investigate the relationship between structure and antimicrobial activity, four shortened analogs, des-L-Arg1, L-Arg(OH)2-K582 A (pentapeptide), des-L-Arg(OH)2-K-582 A (hexapeptide) and their N-acetyl derivatives, were synthesized by the conventional method. None of them, however, showed any antimicrobial activity. Three more analogs, [L-Lys2]K-582 A, [L-Orn2]K-582 A and [L-Arg2]K-582 A, were synthesized. Among them, only [L-Arg2]K-582 A showed substantial activity against Candida krusei and Saccharomyces rouxii, indicating that the presence of a guanidyl side chain at position 2 is an essential factor for the induction of activity.
K-582 A是一种抗生素七肽，其序列为H-L-精氨酸-L-精氨酸（OH）-D-鸟氨酸-L-苏氨酸-D-鸟氨酸-L-赖氨酸-D-酪氨酸-OH（精氨酸（OH），苏式-γ-羟基精氨酸）。为了研究结构与抗菌活性之间的关系，通过常规方法合成了四种缩短的类似物，去-L-精氨酸1、L-精氨酸（OH）2-K582 A（五肽）、去-L-精氨酸（OH）2-K-582 A（六肽）及其N-乙酰基衍生物。然而，它们均未表现出任何抗菌活性。又合成了另外三种类似物，[L-赖氨酸2]K-582 A、[L-鸟氨酸2]K-582 A和[L-精氨酸2]K-582 A。其中，只有[L-精氨酸2]K-582 A对克鲁斯念珠菌和鲁氏酵母表现出显著活性，表明2位存在胍基侧链是诱导活性的关键因素。
