Molecules, Vol. 25, Pages 4009: Synthesis of Potential Haptens with Morphine Skeleton and Determination of Protonation Constants

Molecules, Vol. 25, Pages 4009: Synthesis of Potential Haptens with Morphine Skeleton and Determination of Protonation Constants Molecules doi: 10.3390/molecules25174009 Authors: István Köteles Károly Mazák Gergő Tóth Boglárka Tűz Sándor Hosztafi Vaccination could be a promising alternative warfare against drug addiction and abuse. For this purpose, so-called haptens can be used. These molecules alone do not induce the activation of the immune system, this occurs only when they are attached to an immunogenic carrier protein. Hence obtaining a free amino or carboxylic group during the structural transformation is an important part of the synthesis. Namely, these groups can be used to form the requisite peptide bond between the hapten and the carrier protein. Focusing on this basic principle, six nor-morphine compounds were treated with ethyl acrylate and ethyl bromoacetate, while the prepared esters were hydrolyzed to obtain the N-carboxymethyl- and N-carboxyethyl-normorphine derivatives which are considered as potential haptens. The next step was the coupling phase with glycine ethyl ester, but the reactions did not work or the work-up process was not accomplishable. As an alternative route, the normorphine-compounds were N-alkylated with N-(chloroacetyl)glycine ethyl ester. These products were hydrolyzed in alkaline media and after the work-up process all of the derivatives contained the free carboxylic group of the glycine side chain. The acid-base ...
Source: Molecules - Category: Chemistry Authors: Tags: Article Source Type: research