Asymmetric deuteration of N-acetyl-(Z)-α,β-dehydrotryptophan-(L)-phenylalanine methyl ester produced by (L)-tryptophan 2′,3′-oxidase from Chromobacterium violaceum. A new route for stereospecific labelling of peptides

✍ Scribed by Akli Hammadi; André Ménez; Roger Genet

• Book ID: 104208179
• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 377 KB
• Volume: 53
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(97)10057-6

✦ Synopsis

A novel approach to the synthesis of labelled (2H, ~H) peptides through the catalytic asymmetric reduction of AZTrp containing peptides, using rhodium complexes with chiral diphosphine ligands as the catalysts, is described. Ac-AZTrp-(L)-Phe-OMe is used as a model substrate to study this new route. The (Z)-~dehydropeptide is produced by (L)-tryptophan 2',3'-oxidase from Chromobacterium violaceum in a single step reaction. Diastereomeric excesses up to 98 % have been obtained with (R,R)-dipamp as ligand'in the catalyst. Extremely high stereoselectivities for producing the (L,L)-or (D,L)-isomer could be achieved using the appropriate chiral ligands. This method has good potential for stereospecific labelling (deuteration or tritiation) of peptides.