Abstract: Two glycoconjugated porphines, tetra[2-acetylglucosyl-oxo-phenyl]porphine (T(o-glu)PPH₂) and tetra[3-acetylglycosy-oxo-phenyl]porphine(T(m-glu)PPH₂), were synthesized from the reaction of pyrrole with ortho-acetylglycosylate benzaldehyde and meta-acetylglycosylate benzaldehyde, respectively, by Lindsey's method. Four glycoconjugated metalloporphyrins, chloro[tetra(o-2,3,4,6-O-acetylglucose-1-O-phenyl)porphinato] iron(T(o-glu)PPFeCl), chloro[tetra(o-2,3,4,6-O-acetylglucose-1-O-phenyl)porphinato]manganese, (T(o-glu)PPMnCl), chloro[tetra(m-2,3,4,6-O-acetylglucose-1-O-phenyl)porphinato]iron(T(m-glu)PPFeCl) and chloro[tetra(m-2,3,4,6-O-acetylglucose-1-O-phenyl)porphinato]manganese(T(m-glu)PPMnCl) were prepared from these glycoconjugated porphines. The newly synthesized compounds were characterized by UV-Vis spectroscopy, ¹H NMRand elemental analysis. Cyclohexane oxidation catalyzed by four glycoconjugated metalloporphyrins with PhIOat room temperature and atmospheric pressure were studied. In contrast with metalloporphyrins without sugar groups, the acetylglycosylated metalloporphyrins raised the ratio of cyclohexanol to cyclohexanone and increased the reaction rates and the yields of cyclohexane oxidation. The results of study indicated that the selective catalysis of these acetylglycosylated metalloporphyrins for hydrocarbon oxidation was more close to cytochrome P-450 monooxygenase, and that the kinetics of cyclohexane oxidation catalyzed by acetylglycosylated metalloporphyrins was in consistent with cytochrome P-450 monooxygenase.

Key words: Glycoconjugated metalloporphyrins, Oxidation, Catalysis, Cyclohexane