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Issue 64, 2019
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Subtle chemical modification for enrichment of Fmoc-amino acid at a phospholipid interface

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Abstract

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.

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

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Supplementary files

Article information


Submitted
23 May 2019
Accepted
06 Nov 2019
First published
14 Nov 2019

This article is Open Access

RSC Adv., 2019,9, 37188-37194
Article type
Paper

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

P. G. Argudo, R. Contreras-Montoya, L. Álvarez de Cienfuegos, M. T. Martín-Romero, L. Camacho and J. J. Giner-Casares, RSC Adv., 2019, 9, 37188
DOI: 10.1039/C9RA03896E

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