Synthesis of p-phosphonomethyl-L-phenylalanine using camphor sultam or D-valine as chiral auxiliaries and its incorporation into integrin sequences.
The synthesis of N-Boc-p-phosphonomethyl-L-phenylalanine with two different chiral auxiliaries, camphor sultam or D-valine is described. The preparations have essentially identical properties and have been used to incorporate the amino acid into two integrin peptides as non-hydrolyzable isosteres of phosphotyrosine.
Larsson
E
E
Department of Organic Chemistry, Arrhenius Laboratories, Stockholm University, Sweden.
Lüning
B
B
D000595:Amino Acid Sequence; D002164:Camphor; D016023:Integrins / Q000737:chemistry*; D008969:Molecular Sequence Data; D010649:Phenylalanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D019000:Phosphotyrosine / Q000138:chemical synthesis; D014633:Valine
D016023:Integrins; C083973:4-phosphonomethylphenylalanine; D019000:Phosphotyrosine; D010649:Phenylalanine; D002164:Camphor; D014633:Valine