<i>Z</i>‐protected glutamic acid‐based biodegradable thermoplastic and thermosetting polyesters: Synthesis and characterization

Tadros, R M; Noureddini, Hossein; Timm, D. C.

doi:10.1002/(sici)1097-4628(19990808)73:6<869::aid-app3>3.0.co;2-#

Cited by 3 publications

(4 citation statements)

References 19 publications

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“…Another advantage of these amino acid‐based polymers is the likely low toxicity of their degradation products due to their natural origin. Many amino acid‐based polymers, including polyesters,5, 6 polyamides,7–9 polyesteramides,10–12 poly (ester urethane)s, and poly (ester urea)s,13, 14 and other polymers15–17 have already been synthesized, and those from L ‐phenylalanine ( L ‐Phe), L ‐leucine ( L ‐Leu), and L ‐alanine ( L ‐Ala) can be degraded by hydrolytic enzymes. These polymers were all reported to be optically active, and their enantiomeric compositions greatly affected degradability 18.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and specific biodegradation of novel polyesteramides containing amino acid residues

Fan

Kobayashi

Kise

2001

J. Polym. Sci. A Polym. Chem.

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Novel polyesteramides were synthesized from p‐nitrophenyl esters of sebacic or adipic acids and diamines containing α‐amino acid ester groups. The optimal polymerization condition was 60 °C in N,N‐dimethylformamide. The structures of these polymers were confirmed by IR and NMR. The number‐average molecular weights of these polyesteramides ranged from 2280 to 23,600 (except for the polymers containing glycine residues), depending on the nature of the amino acid used. The biodegradability of the polyesteramides was investigated by in vitro hydrolysis with proteases and a lipase as catalysts in borate buffer solutions. The results indicated that the polymers containing L‐phenylalanine were hydrolyzed most effectively by α‐chymotrypsin, subtilisin Carlsberg, and subtilisin BPN′. The polyesteramides containing other amino acid residues also underwent hydrolysis to different extents, reflecting the substrate specificity of the proteases. Lipase had almost no effect on the hydrolytic degradation of these polyesteramides. The polymers containing glycine residues were hardly decomposed by any of the enzymes used. © 2001 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 39: 1318–1328, 2001

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Section: Introductionmentioning

confidence: 99%

Synthesis and specific biodegradation of novel polyesteramides containing amino acid residues

Fan

Kobayashi

Kise

2001

J. Polym. Sci. A Polym. Chem.

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“…Approximately 0.5 mL of this solution was injected into the gel permeation chromatograph. The complete experimental details have been reported by Tadros et al1…”

Section: Methodsmentioning

confidence: 98%

“…In previous articles1, 2 polymerization, characterization, and biological degradation studies of three polyesters formed from N ‐carbobenzyloxy‐ L ‐glutamic acid (ZGluOH) were reported. The polymers were a linear, heterochain polyester (ZGluOH and ethylene glycol), a crosslinked heterochain polyester (ZGluOH and diglycidyl ether of 1,4‐butanediol), and a crosslinked heterochain aromatic polyester (ZGluOH and diglycidyl ether of bisphenol A).…”

Section: Introductionmentioning

confidence: 99%

“…Approximately 0.5 mL of this solution was injected into the gel permeation chromatograph. The complete experimental details have been reported by Tadros et al 1 For titrations the centrifuged liquid and the remaining solid polymer were dissolved in an excess of chloroform and distilled water. Solubilities for the polymer, oligomers, and monomers resulted in partial separation between the two immiscible liquid phases.…”

Section: Introductionmentioning

confidence: 99%

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Michaelis-Menten kinetics for enzymatic depolymerization of a linear polyester synthesized from Z-protected glutamic acid

Tadros¹,

Noureddini²,

Timm³

2001

J. Appl. Polym. Sci.

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A biodegradable polyester resin was polymerized from N‐benzyloxycarbonyl‐L‐glutamic acid and ethylene glycol. Rhizopus delemar lipase was used as a biocatalyst for the rupture of ester bonds during the hydrolysis studies. Depolymerization was observed to follow a Michaelis–Menten mechanism, with the maximum rate of monomer formation dP/dtmax = 1.12 × 10−8 mol/s and the rate constant Km × 2.03 × 10−4 mol. Subject to initial conditions described by the most probable distribution and Michaelis–Menten–type depolymerization rate expressions, population density distribution dynamics of the polymeric molecules that formed the resin were explicitly described using a deterministic approach. © 2001 John Wiley & Sons, Inc. J Appl Polym Sci 80: 514–520, 2001

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Synthesis and biodegradation of poly(ester amide)s containing amino acid residues: The effect of the stereoisomeric composition of L‐ and D‐phenylalanines on the enzymatic degradation of the polymers

Fan¹,

Kobayashi²,

Kise³

2001

J. Polym. Sci. A Polym. Chem.

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Biodegradable poly(ester amide)s that contained phenylalanine residues in the main chains were synthesized by the polycondensation of di‐p‐nitrophenyl sebacate and phenylalanine 2‐aminoethyl ester. The stereoisomeric composition (L/D ratio) of the phenylalanine residue in the monomer did not affect the yield and molecular weight of the polymer much. From the optical rotations of the polymers, it was found that the L/D ratio of the phenylalanine residue in the polymer was almost equal to the L/D ratio of the phenylalanine residue in the monomer. The biodegradability of the poly(ester amide)s was studied in aqueous solutions with proteases as catalysts. The polymer with 100% L‐phenylalanine residue was effectively degraded by α‐chymotrypsin or subtilisins. However, the replacement of 10% L‐phenylalanine with D‐isomer resulted in a dramatic decrease in degradability. The polymers with less than 30% L‐isomer were hardly degraded by the enzymes. Gel permeation chromatography studies suggested that the solubility of the degradation products in water greatly affected the rate and extent of biodegradation. © 2001 John Wiley & Sons, Inc. J Polym Sci Part A: Polym Chem 40: 385–392, 2002

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Z‐protected glutamic acid‐based biodegradable thermoplastic and thermosetting polyesters: Synthesis and characterization

Cited by 3 publications

References 19 publications

Synthesis and specific biodegradation of novel polyesteramides containing amino acid residues

Synthesis and specific biodegradation of novel polyesteramides containing amino acid residues

Michaelis-Menten kinetics for enzymatic depolymerization of a linear polyester synthesized from Z-protected glutamic acid

Synthesis and biodegradation of poly(ester amide)s containing amino acid residues: The effect of the stereoisomeric composition of L‐ and D‐phenylalanines on the enzymatic degradation of the polymers

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