Efficient synthesis of suitably protected beta-difluoroalanine and gamma-difluorothreonine from L-ascorbic acid.
[reaction: see text] Fluorinated amino acids are useful building blocks for the preparation of biologically active peptides and peptidomimetics with increased metabolic stability. We report here the synthesis of two fluorinated amino acids, beta-difluoroalanine and gamma-difluorothreonine, as analogues of Ser and Thr, respectively. These compounds were suitably protected for Fmoc-based solid-phase peptide synthesis. Once incorporated into peptides, they may serve as alternative substrates or inhibitors of lantibiotic synthetases that posttranslationally dehydrate Ser and Thr residues to dehydroalanine and dehydrobutyrine, respectively.
Li
Gongyong
G
Roger Adams Laboratory, Department of Chemistry, University of Illinois at Urbana-Champaign, 600 South Mathews Avenue, Urbana, Illinois 61801, USA.
van der Donk
Wilfred A
WA
D001205:Ascorbic Acid / Q000737:chemistry*; D005461:Fluorine / Q000737:chemistry; D006836:Hydro-Lyases / Q000378:metabolism; D015394:Molecular Structure; D013912:Threonine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
C467958:difluorothreonine; D005461:Fluorine; D013912:Threonine; D006836:Hydro-Lyases; D001205:Ascorbic Acid