A practical synthesis of optically pure and fully protected L-gamma-carboxyglutamic acid derivatives and its application in peptide synthesis.

Abstract

The optically active and fully protected gamma,gamma-di-t-butyl N-Fmoc-L-gamma-carboxyglutamate was synthesized from the relatively inexpensive D-serine. The overall yield of the synthesis was about 30%. Our studies review that, under TFA and various acidic conditions, L-Gla and its derivatives were stable with no decarboxylation. Finally, gamma,gamma-di-t-butyl N-Fmoc-L-gamma-carboxyglutamate was successfully used in peptide synthesis by Fmoc strategy on solid phase.