Paul Moushumi, Patton Gregory C, van der Donk Wilfred A
Department of Chemistry, University of Illinois at Urbana-Champaign, 600 South Mathews Avenue, Urbana, Illinois 61801, USA.
Biochemistry. 2007 May 29;46(21):6268-76. doi: 10.1021/bi7000104. Epub 2007 May 5.
Lantibiotics are ribosomally synthesized and post-translationally modified peptide antibiotics. The modifications involve dehydration of Ser and Thr residues to generate dehydroalanines and dehydrobutyrines, followed by intramolecular attack of cysteines onto the newly formed dehydro amino acids to produce cyclic thioethers. LctM performs both processes during the biosynthesis of lacticin 481. Mutation of the zinc ligands Cys781 and Cys836 to alanine did not affect the dehydration activity of LctM. However, these mutations compromised cyclization activity when investigated with full length or truncated peptide substrates. Mutation of His725, another residue that is fully conserved in lantibiotic cyclases, to Asn resulted in a protein that still catalyzed dehydration of the substrate peptide and also retained cyclization activity, but at a decreased level compared to that of the wild type enzyme. Collectively, these results show that the C-terminal domain of LctM is responsible for cyclization, that the zinc ligands are critical for cyclization, and that dehydration takes place independently from the cyclization activity. Furthermore, these mutant proteins are excellent dehydratases and provide useful tools to investigate the dehydration activity as well as generate dehydrated peptides for study of the cyclization reaction by wild type LctM.
羊毛硫抗生素是核糖体合成并经翻译后修饰的肽类抗生素。这些修饰包括丝氨酸(Ser)和苏氨酸(Thr)残基脱水生成脱氢丙氨酸和脱氢丁氨酸,随后半胱氨酸对新形成的脱氢氨基酸进行分子内攻击以产生环状硫醚。在乳酸乳球菌素481的生物合成过程中,LctM执行这两个过程。将锌配体半胱氨酸781(Cys781)和半胱氨酸836(Cys836)突变为丙氨酸并不影响LctM的脱水活性。然而,当用全长或截短的肽底物进行研究时,这些突变损害了环化活性。将羊毛硫抗生素环化酶中另一个完全保守的残基组氨酸725(His725)突变为天冬酰胺(Asn),产生的一种蛋白质仍然能够催化底物肽的脱水反应,并且也保留了环化活性,但与野生型酶相比活性水平有所降低。总的来说,这些结果表明,LctM的C末端结构域负责环化,锌配体对环化至关重要,并且脱水反应独立于环化活性发生。此外,这些突变蛋白是优秀的脱水酶,为研究脱水活性以及生成脱水肽以研究野生型LctM的环化反应提供了有用的工具。