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Comparison of Color Development Kinetics of Tanning Reactions of Dihydroxyacetone with Free and Protected Basic Amino Acids

[Image: see text] Sunless tanning has become incredibly prevalent due to the increasing fashionable demand and the awareness of photodamage risks. The brown pigments are induced by dihydroxyacetone (DHA) and amino groups in the stratum corneum (SC) of skin via the Maillard reaction. While most studi...

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Autores principales: Sun, Yufa, Lee, Subin, Lin, Long
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9753197/
https://www.ncbi.nlm.nih.gov/pubmed/36530253
http://dx.doi.org/10.1021/acsomega.2c06124
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author Sun, Yufa
Lee, Subin
Lin, Long
author_facet Sun, Yufa
Lee, Subin
Lin, Long
author_sort Sun, Yufa
collection PubMed
description [Image: see text] Sunless tanning has become incredibly prevalent due to the increasing fashionable demand and the awareness of photodamage risks. The brown pigments are induced by dihydroxyacetone (DHA) and amino groups in the stratum corneum (SC) of skin via the Maillard reaction. While most studies concerning sunless tanning reactions have focused on free amino acids (AAs), little information is available on the impact of the side chain of AAs or proteins on this important reaction in cosmetic chemistry. To explore the reactivity and color development kinetics of different types of amino groups, three basic free AAs (Arg, His, and Lys) and three Nα-protected AAs (Boc-Arg-OH, Boc-His-OH, and Boc-Lys-OH) were used to react with DHA using a simplified model system at different reaction times, pH, and temperatures. Full factorial experiments were employed to design and analyze the effects of these three factors. The browning intensity and color characteristics were quantitatively evaluated. The factorial experiments showed that temperature had the most significant influence on the browning intensity and played a dominant role in the interactions with the reaction time and pH. It was found, for the first time, that Arg and His reacted with DHA more rapidly than Boc-Arg-OH and Boc-His-OH, while Boc-Lys-OH developed a stronger color than Lys under the same conditions, suggesting that ε-NH(2) of a lysine residue in peptides or proteins of SC may play a crucial role in the color development of DHA tanning. This study not only clearly illustrates the capability of the side chain of AAs to produce colored compounds but also provides a deeper understanding of DHA tanning.
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spelling pubmed-97531972022-12-16 Comparison of Color Development Kinetics of Tanning Reactions of Dihydroxyacetone with Free and Protected Basic Amino Acids Sun, Yufa Lee, Subin Lin, Long ACS Omega [Image: see text] Sunless tanning has become incredibly prevalent due to the increasing fashionable demand and the awareness of photodamage risks. The brown pigments are induced by dihydroxyacetone (DHA) and amino groups in the stratum corneum (SC) of skin via the Maillard reaction. While most studies concerning sunless tanning reactions have focused on free amino acids (AAs), little information is available on the impact of the side chain of AAs or proteins on this important reaction in cosmetic chemistry. To explore the reactivity and color development kinetics of different types of amino groups, three basic free AAs (Arg, His, and Lys) and three Nα-protected AAs (Boc-Arg-OH, Boc-His-OH, and Boc-Lys-OH) were used to react with DHA using a simplified model system at different reaction times, pH, and temperatures. Full factorial experiments were employed to design and analyze the effects of these three factors. The browning intensity and color characteristics were quantitatively evaluated. The factorial experiments showed that temperature had the most significant influence on the browning intensity and played a dominant role in the interactions with the reaction time and pH. It was found, for the first time, that Arg and His reacted with DHA more rapidly than Boc-Arg-OH and Boc-His-OH, while Boc-Lys-OH developed a stronger color than Lys under the same conditions, suggesting that ε-NH(2) of a lysine residue in peptides or proteins of SC may play a crucial role in the color development of DHA tanning. This study not only clearly illustrates the capability of the side chain of AAs to produce colored compounds but also provides a deeper understanding of DHA tanning. American Chemical Society 2022-12-01 /pmc/articles/PMC9753197/ /pubmed/36530253 http://dx.doi.org/10.1021/acsomega.2c06124 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Sun, Yufa
Lee, Subin
Lin, Long
Comparison of Color Development Kinetics of Tanning Reactions of Dihydroxyacetone with Free and Protected Basic Amino Acids
title Comparison of Color Development Kinetics of Tanning Reactions of Dihydroxyacetone with Free and Protected Basic Amino Acids
title_full Comparison of Color Development Kinetics of Tanning Reactions of Dihydroxyacetone with Free and Protected Basic Amino Acids
title_fullStr Comparison of Color Development Kinetics of Tanning Reactions of Dihydroxyacetone with Free and Protected Basic Amino Acids
title_full_unstemmed Comparison of Color Development Kinetics of Tanning Reactions of Dihydroxyacetone with Free and Protected Basic Amino Acids
title_short Comparison of Color Development Kinetics of Tanning Reactions of Dihydroxyacetone with Free and Protected Basic Amino Acids
title_sort comparison of color development kinetics of tanning reactions of dihydroxyacetone with free and protected basic amino acids
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9753197/
https://www.ncbi.nlm.nih.gov/pubmed/36530253
http://dx.doi.org/10.1021/acsomega.2c06124
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