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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...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2022
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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. |
format | Online Article Text |
id | pubmed-9753197 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
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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