Direct amidation of poly(gamma-glutamic acid) with benzylamine in dimethyl sulfoxide |
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Authors: | Novak Levente Banyai Istvan Fleischer-Radu Judit Eva Borbély Janos |
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Affiliation: | Department of Colloid and Environmental Chemistry, University of Debrecen, P.O.B. 31, H-4010 Debrecen, Hungary. lnovak@dragon.unideb.hu |
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Abstract: | 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 degrees 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-d(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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