Fabrication of biodegradable poly(ester-amide)s based on tyrosine natural amino acid

Abstract

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, 1H-NMR, specific rotation, elemental and thermogravimetric analysis (TGA) techniques and typical ones by 13C-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.

Effect of silane-modified ZnO on morphology and properties of bionanocomposites based on poly(ester-amide) containing tyrosine linkages

“…The reaction was carried out on a Misonix ultrasonic liquid processor, XL-2000 Series. Ultrasound was a wave of frequency 2.259 10 4 Hz and power 100 W. (3) was synthesized via the reaction of S-tyrosine methyl ester (1) [38] (1.07 g, 5.5 mmol) and isophthaloyl dichloride (2) (0.5 g, 2.5 mmol) in 6 mL of NMP as a solvent at -20°C (Scheme 1) [39].…”

Polymeric nanoparticles: Recent development in synthesis and application

“…Abdolmaleki and coworkers synthesized optically active and potentially biodegradable poly(esteramide)s (PEAs) based on tyrosine amino acid [75]. Nano spherical-shaped spheres of PEAs with average mean diameter as low as 79 up to 500 nm were obtained in this study.…”

“…They expressed that the synthesized NCs are expected to categorize as biologically active materials due to using . Fungal and bacterial colonies grown from soil water extract, 6 days after inoculation on PDA Petri plates: (a) PEA, (b) diol, and (c) control [75] polymer based on biodegradable amino acid [76]. Hu et al [77] studied assembled PNPs from gallic acid (GA) grafted chitosan (CS, GA-g-CS for GA grafted CS) and caseinophosphopeptides (CPP) to deliver (-)-epigallocatechin-3-gallate (EGCG) as novel functional foods.…”

One pot fabrication of optically active and efficient antibacterial poly(amide-benzimidazole-imide)/Ag bionanocomposite

“…Synthetic polymers comprising naturally occurring materials such as amino acids are ideal applicants which show biodegradable properties [33][34][35][36]. Polymers containing amino acid linkages are a new types of functional material characterized as having optical activity, biodegradability (enzymatic degradability) and hydrolysability which their amino acid moieties can be targeted for cleaving by proteases such as α-chymotrypsin, papain, and subtilisins [37].…”