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Issue 45, 2013
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Influence of the tyrosine environment on the second harmonic generation of iturinic antimicrobial lipopeptides at the air–water interface

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Abstract

The second harmonic generation (SHG) response at the air–water interface from the tyrosine-containing natural iturinic cyclo-lipopeptides mycosubtilin, iturin A and bacillomycin D is reported. It is shown that this response is dominated by the single tyrosine residue present in these molecules owing to the large first hyperpolarizability arising from the non-centrosymmetric aromatic ring structure of this amino acid. The SHG response of these iturinic antibiotics is also compared to the response of surfactin, a cyclo-lipopeptide with a similar L,D-amino acid sequence but lacking a tyrosine residue, and PalmATA, a synthetic linear lipopeptide possessing a single tyrosine residue but lacking the amino acid sequence structuring the cycle of the iturinic antibiotics. From the light polarization analysis of the SHG response, it is shown that the tyrosine local environment is critical in defining the SHG response of these peptides at the air–water interface. Our results demonstrate that tyrosine, similar to tryptophan, can be used as an endogenous molecular probe of peptides and proteins for SHG at the air–water interface, paving the way for SHG studies of other tyrosine-containing bioactive molecules.

Graphical abstract: Influence of the tyrosine environment on the second harmonic generation of iturinic antimicrobial lipopeptides at the air–water interface

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Publication details

The article was received on 23 Jul 2013, accepted on 10 Oct 2013 and first published on 11 Oct 2013


Article type: Paper
DOI: 10.1039/C3CP53098A
Citation: Phys. Chem. Chem. Phys., 2013,15, 19919-19924
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    Influence of the tyrosine environment on the second harmonic generation of iturinic antimicrobial lipopeptides at the air–water interface

    M. N. Nasir, E. Benichou, C. Loison, I. Russier-Antoine, F. Besson and P. Brevet, Phys. Chem. Chem. Phys., 2013, 15, 19919
    DOI: 10.1039/C3CP53098A

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