The interaction of L-phenylalanine with a 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) monolayer at the air-water interface was explored using a combination of experimental techniques and molecular dynamics (MD) simulations. By means of Langmuir trough methods and Brewster angle microscopy, L-phenylalanine was shown to significantly alter the interfacial tension and the surface domain morphology of the DPPC film. In addition, confocal microscopy was used to explore the aggregation state of L-phenylalanine in the bulk aqueous phase. Finally, MD simulations were performed to gain molecular-level information on the interactions of L-phenylalanine and DPPC at the interface. Taken together, these results show that L-phenylalanine intercalates into a DPPC film at the air-water interface, thereby affecting the surface tension, phase morphology, and ordering of the DPPC film. The results are discussed in the context of biological systems and the mechanism of diseases such as phenylketonuria.

§J Heyrovský Institute of Physical Chemistry Academy of Sciences of the Czech Republic Dolejškova 3 18223 Prague 8 Czech Republic

†Department of Chemistry and Biochemistry and CIRES University of Colorado at Boulder UCB 215 Boulder Colorado 80309 United States

‡Department of Chemistry and Biochemistry The Ohio State University 100 West 18th Avenue Columbus Ohio 43210 United States

∥Institute of Organic Chemistry and Biochemistry Academy of Sciences of the Czech Republic Flemingovo nám 2 16610 Prague 6 Czech Republic

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