Journal
AMINO ACIDS
Volume 42, Issue 5, Pages 1997-2007Publisher
SPRINGER WIEN
DOI: 10.1007/s00726-011-0931-1
Keywords
Optically active polymer; Tyrosine amino acid; Biodegradable; Poly(ester-amide); Polycondensation
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Funding
- Research Affairs Division, Isfahan University of Technology (IUT)
- National Elite Foundation (NEF)
- Iran Nanotechnology Initiative Council (INIC)
- Center of Excellency in Sensors and Green Chemistry Research (IUT)
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N,N'-Bis[2-(methyl-3-(4-hydroxyphenyl)propanoate)]isophthaldiamide (5), a novel diol monomer containing chiral group, was prepared by the reaction of S-tyrosine methyl ester (3) with isophthaloyl dichloride (4a). A new family of optically active and potentially biodegradable poly(ester-amide)s (PEAs) based on tyrosine amino acid were prepared by the polycondensation reaction of diol monomer 5 with several aromatic diacid chlorides. The resulting new polymers were obtained in good yields with inherent viscosities ranging between 0.25 and 0.42 dL/g and are soluble in polar aprotic solvents. They showed good thermal stability and high optical purity. The synthetic compounds were characterized and studied by FT-IR, H-1-NMR, specific rotation, elemental and thermogravimetric analysis (TGA) techniques and typical ones by C-13-NMR, differential scanning calorimetry (DSC), X-ray diffraction (XRD), and field emission scanning electron microscopy (FE-SEM) analysis. Soil burial test of the diphenolic monomer 5, and obtained PEA6a, and soil enzymatic assay showed that the synthesized diol and its polymer are biologically active and probably biodegradable in soil environment.
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