Header menu link for other important links
X
Galactose oxidase model: Biomimetic enantiomer-differentiating oxidation of alcohols by a chiral copper complex
Sreedevi Mannam, Pandi Mutupandi,
Published in
2009
PMID: 19107892
Volume: 15
   
Issue: 5
Pages: 1086 - 1090
Abstract
An enantiopure analogue of galactose oxidase (GO) was synthesized from an easily and readily available source with a similar activity of GO's in primary alcohol oxidation and enantioselective catalysts for aerobic oxidative kinetic resolution (AORK) of racemic secondary alcohols. Enantiopure (R)-binam was treated with Cu(OTf)2 in toluene at room temperature for one hour to give a (R)-binam-Cu complex. It is found that enantiopure benzoin is an important intermediate in the synthesis of a potent anticancer agent and can been synthesized by enzymatic hydrolysis with benzaldehyde lyase (BAL). The S enantiomer of the racemate is oxidized faster to the corresponding benzil and the slow-reacting R enentiomer of benzoin is recovered in an enantiomerically enriched form. It is also observed that ortho substitution reduces the rate of reaction, while a reduced enentioselectivity is observed in case of ortho-substituted benzoin.
About the journal
JournalChemistry - A European Journal
ISSN09476539
Open AccessNo
Concepts (45)
  •  related image
    Aldehydes
  •  related image
    Biomimetics
  •  related image
    Chirality
  •  related image
    Copper
  •  related image
    Copper compounds
  •  related image
    Electron transitions
  •  related image
    Enantiomers
  •  related image
    Enantioselectivity
  •  related image
    Enzymatic hydrolysis
  •  related image
    Enzymes
  •  related image
    Hydrolysis
  •  related image
    Organic polymers
  •  related image
    Synthesis (chemical)
  •  related image
    Toluene
  •  related image
    BIO MIMETIC
  •  related image
    CHIRAL BENZOINS
  •  related image
    Copper (ii) complexes
  •  related image
    Cu(ii) complexes
  •  related image
    ENANTIOPURE
  •  related image
    ENANTIOSELECTIVE CATALYSTS
  •  related image
    Enzyme models
  •  related image
    Galactose oxidase
  •  related image
    Kinetic resolution
  •  related image
    PRIMARY ALCOHOLS
  •  related image
    Room-temperature (rt)
  •  related image
    SECONDARY ALCOHOLS
  •  related image
    Oxidation
  •  related image
    Alcohol derivative
  •  related image
    BENZOIN
  •  related image
    Fungal protein
  •  related image
    Animal
  •  related image
    Article
  •  related image
    Biological model
  •  related image
    Chemistry
  •  related image
    Isomerism
  •  related image
    Metabolism
  •  related image
    Oxidation reduction reaction
  •  related image
    X ray crystallography
  •  related image
    Alcohols
  •  related image
    Animals
  •  related image
    BENZOIN
  •  related image
    Crystallography, x-ray
  •  related image
    Fungal proteins
  •  related image
    Models, biological
  •  related image
    Oxidation-reduction