Direct Amidation of Poly(gamma-glutamic acid) with Benzylamine In Dimethyl Sulfoxide

Partially benzylamidated, amphipathic poly(gamma-glutamic acid) (BzPGA) was synthesized from poly(gamma-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 degree C, producing...

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Published inBiomacromolecules Vol. 8; no. 5; pp. 1624 - 1632
Main Authors Novak, Levente, Banyai, Istvan, Fleischer-Radu, Judit Eva, Borbely, Janos
Format Journal Article
LanguageEnglish
Published 01.01.2007
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Summary:Partially benzylamidated, amphipathic poly(gamma-glutamic acid) (BzPGA) was synthesized from poly(gamma-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 degree 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 super(1)H and super(13)C 1D and 2D NMR in DMSO-d sub(6). 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.
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ISSN:1525-7797
1526-4602
DOI:10.1021/bm0612182PII:S1525-7797(06)01218-9