Catalytic oxidation of alkenes with a surface-bound metalloporphyrin-peptide conjugate

✍ Scribed by G. Richard Geier III; Tomikazu Sasaki

• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 843 KB
• Volume: 55
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(98)01227-7

✦ Synopsis

A novel surface-bound metalloporphyrin-peptide conjugate was prepared and used to catalytically oxidize alkenes in the presence of iodosylbenzene. The catalyst was found to oxidize a number of alkene substrates in good yield under a variety of reaction conditions. Comparison to control experiments using surface-bound Mn(lII)tetraphenylporphyrin showed differences in oxidation yields and ratios of oxidized products. Substrate competition experiments demonstrated the ability of the conjugate catalyst to discriminate between substrates on the basis of size. Both results suggest oxidative catalysis occurred between the porphyrin ring and the peptide chain with the peptide influencing the outcome of the reaction in accord with the catalyst design.