Chemical optimization of artificial metalloenzymes based on the biotin-avidin technology: (S)-selective and solvent-tolerant hydrogenation catalysts via the introduction of chiral amino acid spacers.
Incorporation of biotinylated-[rhodium(diphosphine)]+ complexes, with enantiopure amino acid spacers, in streptavidin affords solvent-tolerant and selective artificial metalloenzymes: up to 91% ee (S) in the hydrogenation of N-protected dehydroamino acids.
Skander
Myriem
M
Institute of Chemistry, University of Neuchâtel, Switzerland.
Malan
Christophe
C
Ivanova
Anita
A
Ward
Thomas R
TR
D000596:Amino Acids / Q000737:chemistry*; D001710:Biotin / Q000737:chemistry*; D002384:Catalysis; D006865:Hydrogenation; D008024:Ligands; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D010720:Phosphines / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism; D019809:Streptavidin / Q000737:chemistry*
D000596:Amino Acids; D008024:Ligands; D009942:Organometallic Compounds; D010720:Phosphines; D012997:Solvents; D001710:Biotin; D019809:Streptavidin; D012238:Rhodium