2021
DOI: 10.1021/acs.jpcb.1c05572
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Two- and Three-Dimensional Physical–Chemical Characterization of CER[AP]: A Study of Stereochemistry and Chain Symmetry

Abstract: The stratum corneum represents the first skin barrier against chemical and physical damage. These unique properties are based on its peculiar lipid composition with ceramides (CERs) as the main protagonists. In this study, the structural and chemical properties of the α-OH phytosphingosine [AP] CER class have been investigated. α-OH CERs are present in the stratum corneum in their d-forms; however, in most model systems the diastereomer mixture with the synthetically produced l-form is used. The d-form is well… Show more

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Cited by 2 publications
(2 citation statements)
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“…2S, 3R-sphingosine and 2S, 3S, 4R-phytosphingosine) together with Rα-hydroxy fatty acids have recently been studied. 5,6 For at least one marketed ceramide, AP, the α-hydroxy fatty acid component consists of the two diastereomers of which the natural R-isomer promotes tighter lipid packing and the authors conclude that it should be preferred compared with the unnatural S-isomer or the racemic version. 6 The representative structures of other types of molecules (pseudoceramides) that are used in skin-care products are shown in Figure 1b.…”
Section: Comment On "Clinical Significance Of the Water Retention And...mentioning
confidence: 99%
See 1 more Smart Citation
“…2S, 3R-sphingosine and 2S, 3S, 4R-phytosphingosine) together with Rα-hydroxy fatty acids have recently been studied. 5,6 For at least one marketed ceramide, AP, the α-hydroxy fatty acid component consists of the two diastereomers of which the natural R-isomer promotes tighter lipid packing and the authors conclude that it should be preferred compared with the unnatural S-isomer or the racemic version. 6 The representative structures of other types of molecules (pseudoceramides) that are used in skin-care products are shown in Figure 1b.…”
Section: Comment On "Clinical Significance Of the Water Retention And...mentioning
confidence: 99%
“…5,6 For at least one marketed ceramide, AP, the α-hydroxy fatty acid component consists of the two diastereomers of which the natural R-isomer promotes tighter lipid packing and the authors conclude that it should be preferred compared with the unnatural S-isomer or the racemic version. 6 The representative structures of other types of molecules (pseudoceramides) that are used in skin-care products are shown in Figure 1b. Moreover, in comparison to skin ceramides none of these contain intricate esters of long-chain omega-hydroxy fatty acids like those in acylceramides or N-acylated α-hydroxy fatty acids or multiple sphingoid-like base mimics.…”
Section: Comment On "Clinical Significance Of the Water Retention And...mentioning
confidence: 99%