Facile synthesis of DL-4,4-difluoroornithine, DL-4,4-difluoroglutamine, and γ-DL-4,4-difluoroglutamyl-containing peptides: Regiospecific addition of nucleophiles to N-Cbz-di-tert-butyl-DL-4,4-difluoroglutamate

Takashi Tsukamoto, James K. Coward

Research output: Contribution to journalArticlepeer-review

Abstract

The reaction of several nucleophiles with N-Cbz-protected di-tert-butyl-DL-4,4-difluoroglutamate was investigated as an approach to the synthesis of various fluorinated amino acids and peptides. The γ-carboxyl group is highly activated by the two adjacent fluorine atoms, and nucleophilic reactions occurred exclusively at that carbonyl carbon. Further transformations of the reaction products resulted in the synthesis of DL-4,4-difluoroornithine, DL-4,4-difluoroglutamine, and γ-DL-4,4-difluoroglutamyl-contoining dipeptides.

Original languageEnglish (US)
Pages (from-to)2497-2500
Number of pages4
JournalJournal of Organic Chemistry
Volume61
Issue number7
DOIs
StatePublished - Apr 5 1996
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Facile synthesis of DL-4,4-difluoroornithine, DL-4,4-difluoroglutamine, and γ-DL-4,4-difluoroglutamyl-containing peptides: Regiospecific addition of nucleophiles to N-Cbz-di-tert-butyl-DL-4,4-difluoroglutamate'. Together they form a unique fingerprint.

Cite this