聚（γ-谷氨酸）在二甲基亚砜中与苄胺的直接酰胺化反应。

Direct amidation of poly(gamma-glutamic acid) with benzylamine in dimethyl sulfoxide.

作者信息

Novak Levente, Banyai Istvan, Fleischer-Radu Judit Eva, Borbély Janos

机构信息

Department of Colloid and Environmental Chemistry, University of Debrecen, P.O.B. 31, H-4010 Debrecen, Hungary.

出版信息

Biomacromolecules. 2007 May;8(5):1624-32. doi: 10.1021/bm0612182. Epub 2007 Apr 20.

DOI:10.1021/bm0612182

PMID:17444680

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.

摘要

部分苄基酰胺化的两亲性聚（γ-谷氨酸）（BzPGA）是由聚（γ-谷氨酸）（PGA）和苄胺在二甲基亚砜（DMSO）中通过直接酰胺化反应合成的。苄胺和PGA在DMSO中于110至130摄氏度的温度下加热1至26小时，根据反应时间和温度生成不同苄基酰胺化程度的衍生物。该反应无需任何羧基活化剂或催化剂即可进行。通过透析纯化后，产物在氘代二甲亚砜（DMSO-d(6)）中通过1H和13C一维及二维核磁共振（NMR）进行鉴定。通过新的直接酰胺化方法制备的BzPGA与在水中通过传统碳二亚胺介导的反应获得的产物相同。本文所述的一锅法酰胺化过程可能适用于由其他胺和羧酸合成酰胺。