Functional lactide monomers: Methodology and polymerization

Warren W. Gerhardt, David E. Noga, Kenneth I. Hardcastle, Andrés J. García, David M. Collard, Marcus Weck

Research output: Contribution to journalArticle

Abstract

Side-chain-functionalized lactide analogues have been synthesized from commercially available amino acids and polymerized using stannous octoate as a catalyst. The synthetic strategy presented allows for the incorporation of any protected amino acid for the preparation of functionalized diastereomerically pure lactide monomers. The resulting functionalized cyclic monomers can be homopolymerized and copolymerized with lactides and then quantitatively deprotected forming new functional poly(lactide)-based materials. This strategy allows for the introduction of functional groups along a poly(lactide) (PLA) backbone that after deprotection can be viewed as chemical handles for further functionalization of PLA, yielding improved biomaterials for a variety of applications.

Original languageEnglish (US)
Pages (from-to)1735-1742
Number of pages8
JournalBiomacromolecules
Volume7
Issue number6
DOIs
StatePublished - Jun 2006

Fingerprint

Polymerization
Amino acids
Monomers
Biomaterials
Functional groups
Amino Acids
Biocompatible Materials
Catalysts
dilactide
poly(lactide)
2-ethylhexanoic acid tin(II) salt

ASJC Scopus subject areas

  • Organic Chemistry
  • Biochemistry, Genetics and Molecular Biology(all)
  • Polymers and Plastics
  • Materials Chemistry

Cite this

Gerhardt, W. W., Noga, D. E., Hardcastle, K. I., García, A. J., Collard, D. M., & Weck, M. (2006). Functional lactide monomers: Methodology and polymerization. Biomacromolecules, 7(6), 1735-1742. https://doi.org/10.1021/bm060024j

Functional lactide monomers : Methodology and polymerization. / Gerhardt, Warren W.; Noga, David E.; Hardcastle, Kenneth I.; García, Andrés J.; Collard, David M.; Weck, Marcus.

In: Biomacromolecules, Vol. 7, No. 6, 06.2006, p. 1735-1742.

Research output: Contribution to journalArticle

Gerhardt, WW, Noga, DE, Hardcastle, KI, García, AJ, Collard, DM & Weck, M 2006, 'Functional lactide monomers: Methodology and polymerization', Biomacromolecules, vol. 7, no. 6, pp. 1735-1742. https://doi.org/10.1021/bm060024j
Gerhardt WW, Noga DE, Hardcastle KI, García AJ, Collard DM, Weck M. Functional lactide monomers: Methodology and polymerization. Biomacromolecules. 2006 Jun;7(6):1735-1742. https://doi.org/10.1021/bm060024j
Gerhardt, Warren W. ; Noga, David E. ; Hardcastle, Kenneth I. ; García, Andrés J. ; Collard, David M. ; Weck, Marcus. / Functional lactide monomers : Methodology and polymerization. In: Biomacromolecules. 2006 ; Vol. 7, No. 6. pp. 1735-1742.
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