Viitaja , T , Raitanen , J-E , Moilanen , J , Paananen , R O & Ekholm , F S 2021 , ' 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 ' , Journal of Organic Chemistry , vol. 86 , no. 7 , pp. 4965-4976 . https://doi.org/10.1021/acs.joc.0c02882
Title: | 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 |
Author: | Viitaja, Tuomo; Raitanen, Jan-Erik; Moilanen, Jukka; Paananen, Riku O.; Ekholm, Filip S. |
Contributor organization: | Department of Chemistry Helsinki University Hospital Area HUS Head and Neck Center Department of Ophthalmology and Otorhinolaryngology |
Date: | 2021-04-02 |
Language: | eng |
Number of pages: | 12 |
Belongs to series: | Journal of Organic Chemistry |
ISSN: | 0022-3263 |
DOI: | https://doi.org/10.1021/acs.joc.0c02882 |
URI: | http://hdl.handle.net/10138/330328 |
Abstract: | 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. |
Description: | Correction: 10.1021/acs.joc.1c02513. |
Subject: |
114 Physical sciences
Biophysics Evaporation resistance Langmuir Blodgett film 116 Chemical sciences Organic synthesis Lipids OAHFA NMR spectroscopy Diesters 3125 Otorhinolaryngology, ophthalmology TFLL Dry eye syndrome NUCLEAR-MAGNETIC-RESONANCE HUMAN MEIBUM MEIBOMIAN GLAND DRY EYE CHEMICAL-SYNTHESIS AGE CHOLESTERYL EVAPORATION INVESTIGATE MONOLAYERS |
Peer reviewed: | Yes |
Rights: | cc_by |
Usage restriction: | openAccess |
Self-archived version: | publishedVersion |
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