10.1021/jo01303a028
The research describes practical procedures for synthesizing selectively protected a-aminosuberic acid and a,a'-diaminosuberic acid using mixed Kolbe electrolytic decarboxylative dimerization of different carboxylic acids. The purpose of the study is to develop a method for creating these intermediates, which are useful in the preparation of dicarba and desaminodicarba analogues of cystine peptides, known for their high biological activity and enhanced stability due to the absence of reducible disulfide linkages. The key chemicals used include a-tert-butyl N-Boc-L-glutamate (2a), a-methyl N-Cbz-L-glutamate (1), a-tert-butyl N-Boc-D-glutamate (2b), and methyl glutarate (8). The study concludes that by using readily available selectively blocked glutamic acid derivatives and incorporating desired protecting groups and stereochemistry prior to Kolbe dimerization, the desired unsymmetrical dimers can be isolated without racemization of chiral centers. The method provides a practical and efficient way to synthesize optically pure, selectively protected diamino- and monoamino suberic acid derivatives for use in peptide synthesis.
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