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    Subtle chemical modification for enrichment of Fmoc-amino acid at a phospholipid interface

    Year: 2019

    Journal: RSC Adv., Volume 9, 1-Nov, page 37188–37194

    Authors: Argudo, Pablo G.; Contreras-Montoya, Rafael; Alvarez de Cienfuegos, Luis; Martin-Romero, Maria T.; Camacho, Luis; Giner-Casares, Juan J.

    Organizations: Ministry of Science, Innovation and Universities of Spain through the MANA project [CTQ2017-83961-R]; Fondo Europeo de Desarrollo Regional, ERDF, European Union [FIS2017-85954-R]; Ministry of Science, Innovation and Universities [RyC-2014-14956]

    Amino acids including the Fmoc group (9-fluorenylmethyloxycarbonyl) are bioinspired molecules that display intriguing features in self-assembly and biological applications. The influence of a delicate chemical modification between Fmoc-F and Fmoc-Y on the interaction with a phospholipid surface was analyzed. Langmuir monolayers of the 1,2-dimyristoyl-sn-glycero-3-phosphate (DMPA) phospholipid were used to mimic the eukaryotic cell membrane. In situ Brewster angle microscopy and UV-vis reflection spectroscopy provided insights on the effect of the Fmoc-amino acid derivatives on the DMPA phospholipid. The formation of H-bonds between the Fmoc-Y and the DMPA molecules was assessed, demonstrating the crucial role of the hydroxyl group of Fmoc-Y in enhancing the interaction with biosurfaces.
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