Galactose Oxidase Model: Biomimetic Enantiomer‐Differentiating Oxidation of Alcohols by a Chiral Copper Complex

GO for it! An enantiopure galactose oxidase (GO) enzyme model has been synthesized from readily available (R)‐binam and Cu(OTf)2 (see scheme; TEMPO=2,2,6,6‐tetramethyl‐piperidin‐1‐oxyl), and has been effectively used as an efficient chiral catalyst for the oxidative kinetic resolution of secondary a...

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Bibliographic Details
Published in:Chemistry : a European journal 2009-01, Vol.15 (5), p.1086-1090
Main Authors: Alamsetti, Santosh Kumar, Mannam, Sreedevi, Mutupandi, Pandi, Sekar, Govindasamy
Format: Article
Language:English
Subjects:
Alcohols - chemistry
Alcohols - metabolism
Animals
Benzoin - chemistry
Benzoin - metabolism
chiral benzoins
Copper - chemistry
Copper - metabolism
Crystallography, X-Ray
enantioselectivity
enzyme models
Fungal Proteins - chemistry
Fungal Proteins - metabolism
Galactose Oxidase - chemistry
Galactose Oxidase - metabolism
Isomerism
kinetic resolution
Models, Biological
oxidation
Oxidation-Reduction
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Summary:GO for it! An enantiopure galactose oxidase (GO) enzyme model has been synthesized from readily available (R)‐binam and Cu(OTf)2 (see scheme; TEMPO=2,2,6,6‐tetramethyl‐piperidin‐1‐oxyl), and has been effectively used as an efficient chiral catalyst for the oxidative kinetic resolution of secondary alcohols. This is the first chiral copper‐catalyzed oxidative kinetic resolution of racemic benzoins and the simplest method for the synthesis of highly important enantiomerically enriched benzoins.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.200802064