Convenient preparation of 4-(tetrazol-5-yl)-phenylalanine for use in Fmoc-based solid-phase peptide synthesis

✍ Scribed by John S McMurray; Olga Khabashesku; James S Birtwistle; Wei Wang

• Publisher: Elsevier Science
• Year: 2000
• Tongue: French
• Weight: 101 KB
• Volume: 41
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)01135-7

✦ Synopsis

To create a novel amino acid incorporating both acidic and aromatic features, trimethyltin azide was used to synthesize l-4-(tetrazol-5-yl)-phenylalanine (Tpa) and the corresponding d,l racemate by [3+2] cycloadditition of azide to the nitrile group of corresponding 4-cyanophenylalanine analogs. N a -Fmoc-Tpa derivatives, possessing no protection of the tetrazole ring, were well-behaved monomers in the synthesis of a model peptide using standard solid-phase methods.