A practical synthesis of optically pure and fully protected L-gamma-carboxyglutamic acid derivatives and its application in peptide synthesis.
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.
Peninsula Labs, Belmont, CA.
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D015055:1-Carboxyglutamic Acid / Q000031:analogs & derivatives* / Q000737:chemistry*; D000595:Amino Acid Sequence; D004355:Drug Stability; D006801:Humans; D008969:Molecular Sequence Data; D010455:Peptides / Q000138:chemical synthesis*; D013237:Stereoisomerism
D010455:Peptides; D015055:1-Carboxyglutamic Acid