449142-01-2Relevant academic research and scientific papers
Synthesis of new photoactivatable phenylalanine analogues and their incorporation into a model peptide - Phenylseleno derivatives as precursors of α,β-unsaturated ketones in peptide synthesis
Jullian, Valerie,Monjardet-Bas, Veronique,Fosse, Celine,Lavielle, Solange,Chassaing, Gerard
, p. 1677 - 1684 (2007/10/03)
The asymmetric synthesis of (S)-Boc-p-(propanoyl)phenylalanine (10) was performed by alkylation of sultam N-(di- phenylmethylene)glycinate (4). Different pathways for the introduction of a phenylseleno moiety α to the ketone function were investigated. (S)-Boc-p-[2′-(phenylselenenyl)propanoyl]phenylalanine (11) was easily obtained from (S)-Boc-p-(propanoyl)phenylalanine (10). However, the phenylseleno moiety α to the carbonyl group was found to be unstable to the conditions required for solid-phase peptide synthesis. Therefore, (2S)-Boc-p-[2′-(phenylselenenyl)propanoyl]phenylalanine (11) was transformed into Boc-p-[3′-(phenylselenenyl)propanoyl]phenylalanine (13), which was successfully incorporated into the sequence of a model peptide. The corresponding enone function generated under mild acidic conditions was found to be stable in aqueous solution at pH = 7, but suitably reactive upon irradiation. Thus, these phenylalanine analogs bearing an unsaturated ketone represent new photoreactive probes. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
