Enzymatic Synthesis of a Series of Thioglycosides: Analogs of Arbutin with Efficient Antipigmentation Properties Article Swipe
Cédric Peyrot
,
Blanka Didak
,
Laure Guillotin
,
Ludovic Landemarre
,
Pierre Lafite
,
Loı̈c Lemiègre
,
Richard Daniellou
·
YOU?
·
· 2021
· Open Access
·
· DOI: https://doi.org/10.1002/ejoc.202100672
YOU?
·
· 2021
· Open Access
·
· DOI: https://doi.org/10.1002/ejoc.202100672
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 β‐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.
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- Type
- article
- Language
- en
- Landing Page
- https://doi.org/10.1002/ejoc.202100672
- OA Status
- green
- Cited By
- 7
- References
- 45
- Related Works
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- OpenAlex ID
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All OpenAlex metadata
Raw OpenAlex JSON
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https://openalex.org/W3177459077Canonical identifier for this work in OpenAlex
- DOI
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https://doi.org/10.1002/ejoc.202100672Digital Object Identifier
- Title
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Enzymatic Synthesis of a Series of Thioglycosides: Analogs of Arbutin with Efficient Antipigmentation PropertiesWork title
- Type
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articleOpenAlex work type
- Language
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enPrimary language
- Publication year
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2021Year of publication
- Publication date
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2021-06-25Full publication date if available
- Authors
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Cédric Peyrot, Blanka Didak, Laure Guillotin, Ludovic Landemarre, Pierre Lafite, Loı̈c Lemiègre, Richard DaniellouList of authors in order
- Landing page
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https://doi.org/10.1002/ejoc.202100672Publisher landing page
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YesWhether a free full text is available
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greenOpen access status per OpenAlex
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https://hal.science/hal-03331379Direct OA link when available
- Concepts
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Arbutin, Tyrosinase, Chemistry, Melanin, Enzyme, Biochemistry, Glycosylation, Glycoside, Combinatorial chemistry, StereochemistryTop concepts (fields/topics) attached by OpenAlex
- Cited by
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7Total citation count in OpenAlex
- Citations by year (recent)
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2024: 2, 2023: 3, 2022: 2Per-year citation counts (last 5 years)
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45Number of works referenced by this work
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10Other works algorithmically related by OpenAlex
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