ArticleInternational journal of molecular sciences2021
Density Functional Theory-Based Calculation Shed New Light on the Bizarre Addition of Cysteine Thiol to Dopaquinone.
Article in International journal of molecular sciences, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
What it found
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Who cites it
6 citing papers in PubMed, 14 citations in OpenAlex.
- From Monomers to Aggregates: The Influence of Redox State and Structure on the First Excited States of Eumelanin and Pheomelanin.International journal of molecular sciences · 2026Article
- Research progress on pathogenesis of skin pigmentation in chronic liver disease.Biomolecules & biomedicine · 2025Review
- Advances of curcumin in nervous system diseases: the effect of regulating oxidative stress and clinical studies.Frontiers in pharmacology · 2024Review
- Melanogenesis and the Targeted Therapy of Melanoma.Biomolecules · 2022Review
- Disentangling the Puzzling Regiochemistry of Thiol Addition toThe Journal of organic chemistry · 2022Article
- Chemical and biochemical control of skin pigmentation with special emphasis on mixed melanogenesis.Pigment cell & melanoma research · 2021Review
Corrections and comments
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Authors and funding
6 authors at 5 institutions in 3 countries.
Funding
Abstract
Two types of melanin pigments, brown to black eumelanin and yellow to reddish brown pheomelanin, are biosynthesized through a branched reaction, which is associated with the key intermediate dopaquinone (DQ). In the presence of l-cysteine, DQ immediately binds to the -SH group, resulting in the formation of cysteinyldopa necessary for the pheomelanin production. l-Cysteine prefers to bond with aromatic carbons adjacent to the carbonyl groups, namely C5 and C2. Surprisingly, this Michael addition takes place at 1,6-position of the C5 (and to some extent at C2) rather than usually expected 1,4-position. Such an anomaly on the reactivity necessitates an atomic-scale understanding of the binding mechanism. Using density functional theory-based calculations, we investigated the binding of l-cysteine thiolate (Cys-S
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Registered trials
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