Maia Merlani
Tbilisi State Medical University, Georgia
Title: Synthesis of natural biologically active poly[3-(3,4-dihydroxyphenyl)-glyceric acid] analogues
Biography
Biography: Maia Merlani
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•OEt2 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 π-stacked structure between aromatic and carbonyl groups of neighbouring monomeric units, leading to ICT interactions. Although regulated π-stacked structures of a polymer have been prepared for accumulated aromatic groups in the side- and main-chain, such a “hetero π-stacked conformation” of the polymer chain consisting of different types of π-electron systems is unprecedented to the best of our knowledge.
