Straightforward synthesis of non-natural l-chalcogen and l-diselenide N-Boc-protected--amino acid derivativesElectronic supplementary information (ESI) available: 1H and 13C NMR spectra for all new compounds. See DOI: 10.1039/c3ob40879e

• Main Authors: Kawasoko, Cristiane Y, Foletto, Patricia, Rodrigues, Oscar E. D, Dornelles, Luciano, Schwab, Ricardo S, Braga, Antonio L
• Format: Article
• Language: English
• ISSN: 1477-0520; 1477-0539
• DOI: 10.1039/c3ob40879e

The synthesis of new chiral seleno-, telluro-, and thio- N -Boc--amino acids is described herein. These new compounds were prepared through a simple and short synthetic route, from the inexpensive and commercially-available amino acid l -glutamic acid. The products, with a highly modular character, were obtained in good to excellent yields, via hydrolysis of chalcogen pyroglutamic derivatives with overall retention of the l -glutamic acid stereochemistry. Also, an l -diselenide- N -Boc--amino acid was prepared in good yield. This new synthetic route represents an efficient method for preparing new l -chalcogen- and l -diselenide--amino acids with biological potential. A series of new l -chalcogen and l -diselenide- N -Boc--amino acids were synthesized in good to excellent yields in a flexible and modular strategy.