Enzymatic synthesis of a series of thioglycosides: Analogs of arbutin with efficient antipigmentation properties
| Autor: | Laure Guillotin, Ludovic Landemarre, Pierre Lafite, Cédric Peyrot, Richard Daniellou, Loïc Lemiègre, Blanka Didak |
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| Přispěvatelé: | Institut de Chimie Organique et Analytique (ICOA), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université d'Orléans (UO)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), GLYcoDiag, Centre Val de Loire and Bretagne, Jonchère, Laurent, Université d'Orléans (UO)-Centre National de la Recherche Scientifique (CNRS)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Institut de Chimie du CNRS (INC)-Institut National de la Santé et de la Recherche Médicale (INSERM), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), GLYcoDIAG |
| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: |
Glycan
Enzyme catalysts Tyrosinase Arbutin analogs Carbohydrates Enzyme catalysts Thioglycoligase Whitening agents Carbohydrates Melanin chemistry.chemical_compound Hydrolysis Biosynthesis Enzymatic hydrolysis [CHIM] Chemical Sciences [CHIM]Chemical Sciences Physical and Theoretical Chemistry Whitening agents chemistry.chemical_classification biology Arbutin analogs [CHIM.ORGA]Chemical Sciences/Organic chemistry Organic Chemistry Arbutin Glycoside [CHIM.ORGA] Chemical Sciences/Organic chemistry 3. Good health chemistry Biochemistry Thioglycoligase biology.protein |
| Zdroj: | European Journal of Organic Chemistry European Journal of Organic Chemistry, 2021, 2021 (27), pp.3812-3818. ⟨10.1002/ejoc.202100672⟩ European Journal of Organic Chemistry, Wiley-VCH Verlag, 2021, 2021 (27), pp.3812-3818. ⟨10.1002/ejoc.202100672⟩ |
| ISSN: | 1434-193X 1099-0690 |
| DOI: | 10.1002/ejoc.202100672⟩ |
| Popis: | International audience; Arbutin, a natural glycoside, is well known as a commercial tyrosinase inhibitor, and thus, to prevent pigmentary disorders of skin. In fact, tyrosinase is involved in the biosynthesis of melanin, the skin main pigment. However, arbutin is subject to hydrolysis, which limits its bioactivity. In general, thioglycosides are known to be very resistant to both chemical and enzymatic hydrolysis, which increases the interaction time with their biological targets. A biocatalytic approach allowed us to access to thioglycosidic analogs of arbutin in a green approach with good to excellent yields. Such compounds have then been tested as tyrosinase inhibitors as well as inhibitors of melanin transfer from melanocytes to keratinocytes. This latter mechanism takes place via lectin (or lectin-like) receptors present on the cells surface. p-Aminophenyl beta-D-thiogalactopyranoside appears to be an excellent candidate thanks to its tyrosinase inhibitory activity comparable to arbutin, while having the ability to interact with glycan receptors allowing to reduce melanin transfer. |
| Databáze: | OpenAIRE |
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