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    The Properties and Role of O-Acyl-omega-hydroxy Fatty Acids and Type I-St and Type II Diesters in the Tear Film Lipid Layer Revealed by a Combined Chemistry and Biophysics Approach

    Year: 2021

    Journal: J. Org. Chem., Volume 86, APR 2, page 4965–4976

    Authors: Viitaja, Tuomo; Raitanen, Jan-Erik; Moilanen, Jukka; Paananen, Riku O.; Ekholm, Filip S.

    Organizations: Eye and Tissue Bank Foundation; Mary and Georg C. Ehrnrooth Foundation; Ruth and Nils-Erik Stenback Foundation; Swedish Cultural Foundation; Evald and Hilda Nissi Foundation; Biomedicum Helsinki Foundation; Finnish Eye Foundation

    The tear film lipid layer (TFLL) that covers the ocular surface contains several unique lipid classes, including O-acyl-omega-hydroxy fatty acids, type I-St diesters, and type II diesters. While the TFLL represents a unique biological barrier that plays a central role in stabilizing the entire tear film, little is known about the properties and roles of individual lipid species. This is because their isolation from tear samples in sufficient quantities is a tedious task. To provide access to these species in their pure form, and to shed light on their properties, we here report a general strategy for the synthesis and structural characterization of these lipid classes. In addition, we study the organization and behavior of the lipids at the air-tear interface. Through these studies, new insights on the relationship between structural features, such as number of double bonds and the chain length, and film properties, such as spreading and evaporation resistance, were uncovered.
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