Synthesis of beta-hydroxy-beta-(fluoronitrophenyl)alanines: vital components in the assembly of biologically active cyclic peptides.
[formula: see text] Numerous biologically active cyclic peptides, such as the antibiotic vancomycin, contain amino acid residues connected through side-chain biaryl or aryl-alkyl ether linkages. Nucleophilic aromatic substitution reactions have recently been shown to provide a general method for the formation of such ether linkages, and consequently the synthesis of functionalized fluoronitro-substituted aromatic amino acids is of great interest. Herein, a method for the stereospecific synthesis of 3-fluoro-4-nitro- and 4-fluoro-3-nitro-threo-beta-hydroxyphenylalanine is described.
Hutton
C A
CA
School of Chemistry, University of Sydney, NSW, Australia. c.hutton@chem.usyd.edu.au
D000409:Alanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D009578:Nitrobenzenes / Q000138:chemical synthesis*; D010456:Peptides, Cyclic / Q000138:chemical synthesis*; D013237:Stereoisomerism
D009578:Nitrobenzenes; D010456:Peptides, Cyclic; D000409:Alanine