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

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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.

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Acknowledgments

We wish to express our gratitude to the Research Affairs Division, Isfahan University of Technology (IUT) for financial support. Further financial support from National Elite Foundation (NEF), Iran Nanotechnology Initiative Council (INIC), and Center of Excellency in Sensors and Green Chemistry Research (IUT) is gratefully acknowledged.

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Authors and Affiliations

  1. Department of Chemistry, Isfahan University of Technology, 84156-83111, Isfahan, Iran

    Amir Abdolmaleki & Sedigheh Borandeh

  2. Nanotechnology and Advanced Materials Institute, Isfahan University of Technology, 84156-83111, Isfahan, Iran

    Amir Abdolmaleki & Shadpour Mallakpour

  3. Organic Polymer Chemistry Research Laboratory, Department of Chemistry, Isfahan University of Technology, 84156-83111, Isfahan, Iran

    Shadpour Mallakpour

  4. Department of Agronomy and Plant Breeding, College of Agriculture, Isfahan University of Technology, 84156-83111, Isfahan, Iran

    Mohammad R. Sabzalian

Authors
  1. Amir Abdolmaleki
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  2. Shadpour Mallakpour
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  3. Sedigheh Borandeh
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  4. Mohammad R. Sabzalian
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Correspondence to Amir Abdolmaleki or Shadpour Mallakpour.

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Abdolmaleki, A., Mallakpour, S., Borandeh, S. et al. Fabrication of biodegradable poly(ester-amide)s based on tyrosine natural amino acid. Amino Acids 42, 1997–2007 (2012). https://doi.org/10.1007/s00726-011-0931-1

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  • DOI: https://doi.org/10.1007/s00726-011-0931-1

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