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

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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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