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Note | Special issue | Vol 67, No. 1, 2006, pp.421-431
Published online, 13th September, 2005
DOI: 10.3987/COM-05-S(T)44
Facile Synthesis of (S)-5,5-Difluoronorleucine and Its Incorporation in Biologically Active Peptides as an Methionine Mimetic

Satoshi Osada,* Takako Ishimaru, Hiroshi Kawasaki, and Hiroaki Kodama

*Faculty of Science and Engineering, Saga University, Honjo 1, Saga, Saga 840-8502, Japan

Abstract

Both Boc and Fmoc protected 5,5-difluoronorleucines (F2Nle) were easily prepared from commercially available amino acid derivatives. F2Nle can be viewed as a mimic of methionine in which the sulfur atom is replaced by the CF2 moiety. Two analogues of methionine-containing biologically active peptides (fMLP and Met-enkephalin) were prepared. The validity of CF2-substituted methionine analogues was confirmed in their biological assay.