Direct amidation of poly(γ-glutamic acid) with benzylamine dimethyl sulfoxide

Levente Novḱ, I. Bányai, Judit Éva Fleischer-Radu, J. Borbély

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

Partially benzylamidated, amphipathic poly(γ-glutamic acid) (BzPGA) was synthesized from poly(γ-glutamic acid) (PGA) and benzylamine by direct amidation in dimethyl sulfoxide (DMSO). Benzylamine and PGA were heated in DMSO for 1 to 26 h at temperatures between 110 and 130 °C, producing derivatives of various degrees of benzylamidation as a function of the reaction time and temperature. Neither any carboxyl-activating agent nor catalyst is needed for the reaction to proceed. After purification by dialysis, the product was identified by 1H and 13C 1D and 2D NMR in DMSO-d6. BzPGA prepared by the new direct amidation method was identical to that obtained with a conventional carbodiimide-mediated reaction in water. The one-pot amidation procedure described in the present article can probably be applied to the synthesis of amides from other amines and carboxylic acids.

Original languageEnglish
Pages (from-to)1624-1632
Number of pages9
JournalBiomacromolecules
Volume8
Issue number5
DOIs
Publication statusPublished - May 2007

Fingerprint

Dimethyl sulfoxide
Dimethyl Sulfoxide
Prostaglandins A
Glutamic Acid
Acids
Carbodiimides
Temperature
Dialysis
Carboxylic Acids
Carboxylic acids
Amides
Amines
Purification
Nuclear magnetic resonance
Derivatives
Catalysts
Water
benzylamine
benzylamidated poly(gamma-glutamic acid)

ASJC Scopus subject areas

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

Cite this

Direct amidation of poly(γ-glutamic acid) with benzylamine dimethyl sulfoxide. / Novḱ, Levente; Bányai, I.; Fleischer-Radu, Judit Éva; Borbély, J.

In: Biomacromolecules, Vol. 8, No. 5, 05.2007, p. 1624-1632.

Research output: Contribution to journalArticle

Novḱ, Levente ; Bányai, I. ; Fleischer-Radu, Judit Éva ; Borbély, J. / Direct amidation of poly(γ-glutamic acid) with benzylamine dimethyl sulfoxide. In: Biomacromolecules. 2007 ; Vol. 8, No. 5. pp. 1624-1632.
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