Synthesis and properties of novel biodegradable polyamides containing α-amino acids

Okamura, Ai; Hirai, Tsuneo; Tanihara, Masao; Yamaoka, Tetsuji

doi:10.1016/s0032-3861(02)00111-8

Cited by 49 publications

(29 citation statements)

References 10 publications

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“…21 In this article we examine whether it is possible to synthesize a high molecular weight collagen-like polypeptide by the direct polycondensation of (ProHyp-Gly) n , where n ¼ 1, 5, and 10, according to the method reported previously, and assess the physical properties of the obtained polypeptide, such as its triple-stranded helical structure, thermal stability, and nanostructure.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of poly(Pro–Hyp–Gly)_n by direct polycondensation of (Pro–Hyp–Gly)_n, where n = 1, 5, and 10, and stability of the triple‐helical structure

et al. 2005

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Pro-Hyp-Gly is a characteristic amino acid sequence found in fibrous collagens, and (Pro-Hyp-Gly)(10), which has been widely used as a collagen-model peptide, forms a stable triple-helical structure. Here, we synthesized polypeptides consisting of the Pro-Hyp-Gly sequence by direct poly-condensation of (Pro-Hyp-Gly)(n), where n=1, 5, and 10, using 1-hydroxybenzotriazole and 1-ethyl-3-(3-dimethyl-aminopropyl)-carbodiimide hydrochloride in both phosphate buffer (pH=7.4) and dimethylsulfoxide (DMSO) solutions for 48 h at 20 degrees C. The reaction of (Pro-Hyp-Gly)(5) and (Pro-Hyp-Gly)(10) in DMSO successfully gave polypeptides with molecular weights over 10,000, whereas low molecular weight products were obtained by reaction in phosphate buffer (pH=7.4). In contrast, Pro-Hyp-Gly at a concentration of 50 mg/mL in phosphate buffer (pH=7.4) gave polypeptides with molecular weights over 10,000. The Fourier transform infrared (FTIR) and (1)H nuclear magnetic resonance (NMR) spectra of poly(Pro-Hyp-Gly)(10) revealed that the polymerization of (Pro-Hyp-Gly)(10) described in this report had no side reactions. Each polypeptide obtained shows a collagen-like triple-helical structure, and the triple-helical structures of poly(Pro-Hyp-Gly) and poly(Pro-Hyp-Gly)(10) were stable up to T=80 degrees C, which suggests that the high molecular weight promotes stability of the triple-helical structure, in addition to the high Hyp content. Furthermore, transmission electron microscopy (TEM) observations show that poly(Pro-Hyp-Gly)(10) aggregates to form nanofiber-like structures about 10 nm in width, which suggests that a Pro-Hyp-Gly repeating sequence contains enough information for triple-helix formation, and for subsequent nanofiber-like structure formation.

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Section: Introductionmentioning

confidence: 99%

Synthesis of poly(Pro–Hyp–Gly)_n by direct polycondensation of (Pro–Hyp–Gly)_n, where n = 1, 5, and 10, and stability of the triple‐helical structure

et al. 2005

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“…Biodegradation of synthetic polymers is an important property in their many applications such as drug delivery, gene transfer, tissue engineering, and regenerative medicine. [6][7][8][9] The synthesis and applications of optically active polymers are topics that nowadays attract much attention. These materials have exhibited many interesting properties such as chiral stationary phases for resolution of enantiomers in chromatographic techniques, chiral liquid crystals in ferroelectrics and nonlinear optical devices.…”

Section: Introductionmentioning

confidence: 99%

In vitrostudies on biodegradable chiral nanostructure poly(amide-imide)s containing different natural amino acids in green medium

Mallakpour

Iderli

Rahimmalek

2013

Designed Monomers and Polymers

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α-Amino acids, as one type of the major building blocks of living systems, are the principal components of all naturally occurring peptides and proteins. The aim of this paper was to synthesize and characterize of novel chiral nanostructured poly(amide-imide)s (PAIs) that are biologically active and biodegradable under a natural environment. PAIs were prepared from the polycondensation reaction of optically active diacids monomers containing different natural amino acids with 4,4′-methylene bis(3-chloro-2,6-diethylaniline) in molten tetrabutylammonium bromide as a green solvent. In vitro fungal colonization and weight loss studies showed that the synthetic polymer having alanine amino acid is biologically more active compared to the other components, nontoxic to microbial growth and could be classified as biodegradable compounds. The synthesized PAIs were characterized by different techniques. The field-emission scanning electron microscopy showed that the obtained PAIs were nanostructured polymers.

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“…1,2 In addition, they have played important roles in metal chelation, ion exchange, drug delivery, fiber modification and inhibition of gas hydrate crystal growth in deep sea drilling. [3][4][5][6][7][8] For preparation of water soluble polyamides, several methods can be used: (a) polycondensation of amino acids to form polypeptides and polyamides [9][10][11][12][13] ; (b) polymerization between certain hydrophilic diacids (or acid derivatives) and diamines [14][15][16][17][18] ; and (c) enzymatic production of certain poly(amino acid)s by bacteria. 9,[19][20][21] Among the water-soluble polyamides, poly(aspartic acid)s (PASPs) have been recognized as eco-friendly water-soluble synthetic poly(amino acid)s and used as dispersants, metal chelators, detergent builders, and in biomedical applications.…”

Section: Introductionmentioning

confidence: 99%

Preparation of aqueous soluble polyamides from renewable succinic acid and citric acid as a new approach to design bio‐inspired polymers

Jiang

Chen

et al. 2013

J of Applied Polymer Sci

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A novel type of aqueous soluble polyamides were prepared as renewable substitutes for ecologically benign poly(aspartic acid) by polymerization of succinic acid ester and hexamethylene diamine in the presence of citric acid ester. The copolymerization resulted in the formation of poly(amide imide) intermediates, which were hydrolyzed to aqueous solutions of polyamides. The hydrolyzed products were confirmed to be copolymers of succinamide and citramide with COOH side chains, similar to poly(aspartic acid). The polyamides showed strong chelating abilities to Ca 21 and Pb 21 metals, comparable to poly(aspartic acid). Interestingly, they also demonstrated antifreeze activities in water by reducing the ice fractions. The polyamides represent a new class of metal chelators and antifreeze protein mimics derived from succinamide and citramide.

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Synthesis and properties of novel biodegradable polyamides containing α-amino acids

Cited by 49 publications

References 10 publications

Synthesis of poly(Pro–Hyp–Gly)_n by direct polycondensation of (Pro–Hyp–Gly)_n, where n = 1, 5, and 10, and stability of the triple‐helical structure

Synthesis of poly(Pro–Hyp–Gly)_n by direct polycondensation of (Pro–Hyp–Gly)_n, where n = 1, 5, and 10, and stability of the triple‐helical structure

In vitrostudies on biodegradable chiral nanostructure poly(amide-imide)s containing different natural amino acids in green medium

Preparation of aqueous soluble polyamides from renewable succinic acid and citric acid as a new approach to design bio‐inspired polymers

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Synthesis and properties of novel biodegradable polyamides containing α-amino acids

Cited by 49 publications

References 10 publications

Synthesis of poly(Pro–Hyp–Gly)n by direct polycondensation of (Pro–Hyp–Gly)n, where n = 1, 5, and 10, and stability of the triple‐helical structure

Synthesis of poly(Pro–Hyp–Gly)n by direct polycondensation of (Pro–Hyp–Gly)n, where n = 1, 5, and 10, and stability of the triple‐helical structure

In vitrostudies on biodegradable chiral nanostructure poly(amide-imide)s containing different natural amino acids in green medium

Preparation of aqueous soluble polyamides from renewable succinic acid and citric acid as a new approach to design bio‐inspired polymers

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Synthesis of poly(Pro–Hyp–Gly)_n by direct polycondensation of (Pro–Hyp–Gly)_n, where n = 1, 5, and 10, and stability of the triple‐helical structure

Synthesis of poly(Pro–Hyp–Gly)_n by direct polycondensation of (Pro–Hyp–Gly)_n, where n = 1, 5, and 10, and stability of the triple‐helical structure