Enantioselective synthesis and antioxidant activity of 3-(3,4-dihydroxyphenyl)-glyceric acid-Basic monomeric moiety of a biologically active polyether fromSymphytum asperumandS. caucasicum
| Autor: | Bezhan Chankvetadze, Vakhtang Barbakadze, E. Yannakopoulou, Lali Gogilashvili, Kyriakos Papadopoulos, Maia Merlani, Lela Amiranashvili |
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| Rok vydání: | 2010 |
| Předmět: |
Glyceric acid
Stereochemistry Alkylation Glyceric Acids Hydroxylation Catalysis Substrate Specificity Analytical Chemistry chemistry.chemical_compound Caffeic Acids Picrates Drug Discovery Organic chemistry Moiety Chromatography High Pressure Liquid Spectroscopy Pharmacology biology Spectrum Analysis Biphenyl Compounds Organic Chemistry Enantioselective synthesis Stereoisomerism Free Radical Scavengers Boraginaceae biology.organism_classification Hypochlorous Acid Chiral column chromatography chemistry Enantiomer Sharpless asymmetric dihydroxylation Symphytum asperum |
| Zdroj: | Chirality. |
| ISSN: | 1520-636X 0899-0042 |
| DOI: | 10.1002/chir.20823 |
| Popis: | The racemic and enantioselective synthesis of a novel glyceric acid derivative, namely, 2,3-dihydroxy-3-(3,4-dihydroxyphenyl)-propionic acid as well as the antioxidant activities is described. The virtually pure enantiomers, (+)-(2R,3S)-2,3-dihydroxy-3-(3,4-dihydroxyphenyl)-propionic acid and (-)-(2S,3R)-2,3-dihydroxy-3-(3,4-dihydroxyphenyl)-propionic acid were synthesized for the first time via Sharpless asymmetric dihydroxylation of trans-caffeic acid derivatives using the enantiocomplementary catalysts, (DHQD)(2)-PHAL and (DHQ)(2)-PHAL. The determination of enantiomeric purity of the novel chiral glyceric acid derivatives was performed by high-performance liquid chromatographic techniques on the stage of their alkylated precursors. The novel glyceric acid derivatives show strong antioxidant activity against hypochlorite and N,N-diphenyl-N-picryl-hydrazyl free radical. Their antioxidant activity is about 40-fold higher than that of the corresponding natural polyether and three-fold higher of trans-caffeic acid itself. |
| Databáze: | OpenAIRE |
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