ArticleThe Journal of organic chemistry2023
Synthesis and Photophysical Properties of Charge-Transfer-Based Pyrimidine-Derived α-Amino Acids.
Article in The Journal of organic chemistry, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed, 11 citations in OpenAlex.
- Synthesis, Computational, DFT Calculations, Photophysical and Docking Studies of Novel Fluorescent Pyrimidine-Chlorothymol Hybrid as Potent Antimicrobial Agent.Journal of fluorescence · 2025Article
- Expanding the fluorescence toolkit: molecular design, synthesis and biological application of unnatural amino acids.Chemical science · 2025Review
- DyeLeS: a web platform for predicting and classifying fluorescence properties of bioactive molecules.RSC advances · 2025Article
- Stereoselective Synthesis ofThe Journal of organic chemistry · 2024Article
- Synthesis of β-Pyridyl α-Amino Acids: Conformationally Sensitive Charge Transfer-Based Fluorophores.Organic letters · 2024Article
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The four-step synthesis of fluorescent pyrimidine-derived α-amino acids from an l-aspartic acid derivative is described. The key synthetic steps involved preparation of ynone intermediates via the reaction of alkynyl lithium salts with a Weinreb amide, followed by an ytterbium-catalyzed heterocyclization reaction with amidines. Variation of substituents at the C2- and C4-position of the pyrimidine ring allowed tuning of the photoluminescent properties of the α-amino acids. This revealed that a combination of highly conjugated or electron-rich aryl substituents with the π-deficient pyrimidine motif resulted in fluorophores with the highest quantum yields and overall brightness. Further analysis of the most fluorogenic α-amino acid demonstrated solvatochromism and sensitivity to pH.
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Registered trials
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