Bobone Sara, De Zotti Marta, Bortolotti Annalisa, Biondi Barbara, Ballano Gema, Palleschi Antonio, Toniolo Claudio, Formaggio Fernando, Stella Lorenzo
Department of Chemical Sciences and Technologies, University of Rome Tor Vergata, 00133, Rome, Italy.
Department of Chemistry, University of Padova, 35131, Padova, Italy.
Biopolymers. 2015 Sep;104(5):521-32. doi: 10.1002/bip.22674.
Total syntheses and complete characterizations of singly substituted PheCN -based analogs of alamethicin AlaP, which is active on model and natural membranes, and the TM peptide, which inserts in a transmembrane orientation in lipid bilayers, are reported. The syntheses of the AlaP analogs were performed in solution, while those of TM and its analogs were carried out by solid phase. Using the cyanophenyl fluorescence and infrared (IR) absorption probe, an in-depth investigation of the self-association, membrane-interacting, permeabilizing, and orientation properties of these peptides were conducted. The aromatic residue incorporated induces only a negligible modification to the properties of the parent peptides. The PheCN IR absorption band was located between 2228 and 2230 cm(-1) for all peptides, irrespective of the position of labeling. By contrast, as the width of this band varied significantly with the depth of probe insertion in the bilayer, it could represent a good marker of the PheCN position in phospholipid membranes.
报道了对阿拉米辛AlaP的单取代苯丙氨酸腈（PheCN）基类似物以及跨膜（TM）肽的全合成和完整表征。阿拉米辛AlaP对模型膜和天然膜具有活性，而TM肽以跨膜方向插入脂质双层中。AlaP类似物的合成在溶液中进行，而TM及其类似物的合成则通过固相进行。使用氰基苯基荧光和红外（IR）吸收探针，对这些肽的自缔合、膜相互作用、通透和取向性质进行了深入研究。引入的芳香族残基对亲本肽的性质仅产生可忽略不计的修饰。所有肽的苯丙氨酸腈红外吸收带位于2228至2230 cm(-1)之间，与标记位置无关。相比之下，由于该带的宽度随探针插入双层的深度而显著变化，它可能是磷脂膜中苯丙氨酸腈位置的良好标记。
