Visible light-absorbing biocompatible polymers based on L-lactide and aminosugars

Preparation and characterization

Maciej Skotak, Gustavo Larsen

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Two series of polymers with low-molecular-weight L-lactide side-arms were prepared by ring-opening polymerization using D-glucosamine and N-acetyl-D-glucosamine as polymer core molecules, and methanesulfonic acid as solvent and catalyst. This simple synthetic route does not rely on the use of organometallic catalysts, and has also proven useful to the authors for chitosan grafting with lactones. NMR spectroscopy reveals a high degree of substitution (>3), and Fourier transform infrared/NMR spectra suggest the existence of three different lactate tautomers likely to be responsible for coloration. These D-glucosamine-based polymers also display glass transition temperatures approximately 10 °C above that of the human body, which points to the potential of these lactone-grafted aminosugars with tunable amphiphilic character in the design of submicrometer-sized drug delivery vehicles. They are also viewed as interesting hydrophobic chelating agents for catalytic transition metal centers.

Original languageEnglish (US)
Pages (from-to)1331-1338
Number of pages8
JournalPolymer International
Volume59
Issue number10
DOIs
StatePublished - Oct 1 2010

Fingerprint

Glucosamine
Polymers
Lactones
Catalysts
Acetylglucosamine
Ring opening polymerization
Chitosan
Organometallics
Chelating Agents
Chelation
Drug delivery
Nuclear magnetic resonance spectroscopy
Transition metals
Lactic Acid
Fourier transforms
Substitution reactions
Molecular weight
Nuclear magnetic resonance
Infrared radiation
Molecules

Keywords

  • Biocompatibility
  • L-lactide
  • Ring-opening polymerization
  • Tautomerism

ASJC Scopus subject areas

  • Polymers and Plastics

Cite this

Visible light-absorbing biocompatible polymers based on L-lactide and aminosugars : Preparation and characterization. / Skotak, Maciej; Larsen, Gustavo.

In: Polymer International, Vol. 59, No. 10, 01.10.2010, p. 1331-1338.

Research output: Contribution to journalArticle

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