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Synthesis of unnatural amino acids functionalized with sterically shielded pyrroline nitroxides.

ABSTRACT: A series of unnatural amino acids functionalized with sterically shielded pyrroline nitroxides were synthesized. Their reduction by ascorbate/glutathione indicates that L-cysteine functionalized with gem-diethylpyrroline nitroxide is reduced at the slowest rate and is comparable to that measured for the most resistant to reduction pyrroline and pyrrolidine nitroxides.

SUBMITTER: Wang Y

PROVIDER: S-EPMC4201325 | biostudies-literature | 2014 Oct

REPOSITORIES: biostudies-literature

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Synthesis of unnatural amino acids functionalized with sterically shielded pyrroline nitroxides.

Wang Ying Y Paletta Joseph T JT Berg Kathleen K Reinhart Erin E Rajca Suchada S Rajca Andrzej A

Organic letters 20140916 20

A series of unnatural amino acids functionalized with sterically shielded pyrroline nitroxides were synthesized. Their reduction by ascorbate/glutathione indicates that L-cysteine functionalized with gem-diethylpyrroline nitroxide is reduced at the slowest rate and is comparable to that measured for the most resistant to reduction pyrroline and pyrrolidine nitroxides. ...[more]

PMID: 25324010

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Project description:ObjectivesThis work aimed to design, synthesize and characterize replacement natural moisturizing factor (NMF) composed of modified hygroscopic linear amino acids to pre-empt or repair skin barrier dysfunction.MethodsFollowing synthesis and characterization, thermo-gravimetric analysis and quantum mechanics molecular modelling quantified and depicted water binding to the new compounds. Deliquescence relative humidity demonstrated the water-scavenging ability of the compounds, whereas snake skin moisturizing studies showed they increased water uptake into snake skin.ResultsFrom thermal analysis, N-hydroxyglycine showed greatest water-holding capacity followed by N-hydroxyserine, l-homoserine and ?-hydroxyglycine; coupled with quantum mechanics molecular modelling, between 8 and 12 molecules of water could associate with each molecule of either N-hydroxyglycine, N-hydroxyserine or l-homoserine. All of our modified amino acids were efficacious and induced similar or greater water uptake compared with the established moisturizing compounds hyaluronic acid, glycerine and urea in snake skin. Incorporated at 10% in Oilatum, N-hydroxyserine induced >200% greater moisture uptake into dry snake skin compared to treatment with water alone, with efficacy related to the molecule structure and ability to bind to 12 water molecules. Oilatum cream spiked with all our unnatural amino acid hydrotropes increased water uptake into snake skin compared with Oilatum alone. The compound series was designed to elucidate some structure - efficacy relationships. Amino acid chirality did not affect the water-holding capacity but did affect uptake into skin. Compounds with high melting points and bond energies tended to decrease water-holding capacity. With isosteric replacement, the more electronegative atoms gave greater water-holding capacities.ConclusionsThis work demonstrates the potential of unnatural amino acid hydrotropes as skin moisturizers and has developed some predictive 'rules' for further design and refinement of chemical structures.

Dataset Information

Synthesis of unnatural amino acids functionalized with sterically shielded pyrroline nitroxides.

Publications

Synthesis of unnatural amino acids functionalized with sterically shielded pyrroline nitroxides.

Similar Datasets

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