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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

Skander, Myriem and Malan, Christophe and Ivanova, Anita and Ward, Thomas R.. (2005) 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. Chemical Communications, 41 (38). pp. 4815-4817.

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Official URL: http://edoc.unibas.ch/dok/A5254477

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Abstract

The selective artificial metalloenzymes were designed by incorporation of amino acid spacer (phenylalanine or proline) between biotin anchor and the rhodium-diphosphate moiety. The two pairs of epimeric ligands, biotin-phenylalanine and biotin-proline, were prepd. in three steps from com. available N-Boc-protected amino acids (Boc = tert-butoxycarbonyl). Incorporation of biotinylated [rhodium(diphosphine)]+ complexes with enantiopure amino acid spacers in streptavidin affords solvent-tolerant and selective artificial metalloenzymes. Catalytic hydrogenation of N-protected dehydroamino acids using prepd. artificial metalloenzymes gives up to 91% ee (S). [on SciFinder(R)]
Faculties and Departments:05 Faculty of Science > Departement Chemie > Chemie > Bioanorganische Chemie (Ward)
UniBasel Contributors:Ward, Thomas R. R.
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:Royal Society of Chemistry
ISSN:0022-4936
Note:Publication type according to Uni Basel Research Database: Journal article
Identification Number:
Last Modified:01 Dec 2016 07:30
Deposited On:22 Mar 2012 14:07

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