Synthesis of natural biologically active poly[3-(3,4-dihydroxyphenyl)-glyceric acid] analogues

Chemical Sciences Journal

ISSN: 2150-3494

Open Access

Synthesis of natural biologically active poly[3-(3,4-dihydroxyphenyl)-glyceric acid] analogues

European Chemistry Congress

June 16-18, 2016 Rome, Italy

Maia Merlani, Vakhtang Barbakadze, Lela Amiranashvili, Lali Gogilashvili and Tamaki Nakano

Tbilisi State Medical University, Georgia
CRC Hokkaido University, Japan

Scientific Tracks Abstracts: Chem Sci J

Abstract :

The caffeic acid-derived polyether poly[3-(3,4-dihydroxyphenyl)glyceric acid] (PDPGA) isolated from comfrey species is a biologically active, water soluble polymer with antioxidant, antilipoperoxidant, antiinflammatory and anticancer properties. This compound is a representative of a new class of natural polyethers The first step for obtaining of PDPGA analogue was performed by cationic polymerization of 2-methoxycarbonyl-3-(3,4-dimethoxyphenyl)-oxirane (MCDMPO). An unsymmetrically 2,3-disubstituted oxirane monomer was synthesized from veratraldehyde (3,4-dimethoxybenzaldehyde, methyl vanillin) and methyl chloroacetate. MCDMPO was polymerized using BF3├?┬ĚOEt2 in CH2Cl2 under various conditions. Under all conditions examined, the monomer was almost completely consumed to afford a polymer. Mn of the polymer ranged from 2900 to 12 800 as determined by size-exclusion chromatography (SEC) with right-angle laser light scattering detection. MCDMPO leads to a polymer having a rather stiff conformation having a novel ├Ć┬?-stacked structure between aromatic and carbonyl groups of neighbouring monomeric units, leading to ICT interactions. Although regulated ├Ć┬?-stacked structures of a polymer have been prepared for accumulated aromatic groups in the side- and main-chain, such a ├ó┬?┬?hetero ├Ć┬?-stacked conformation├ó┬?┬Ł of the polymer chain consisting of different types of ├Ć┬?-electron systems is unprecedented to the best of our knowledge.

Biography :

Maia Merlani has completed her PhD from Tbilisi State University. She is Senior Research Scientist at Tbilisi State Medical University and at the same time holds a position of an Assistant Professor at Caucasian International University. Her field of interest is a chemistry and synthesis of natural compounds. She is the author of more than 45 papers in reputed journals and presentations at 55 international scientific conferences. She was granted Georgian Presidential scholarship for young scientists (1997), NATO scholarship (2002) and Matstumae International foundation scholarship (2013).

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