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Synfacts 2006(5): 0506-0506  
DOI: 10.1055/s-2006-934453
Bioorganic Chemistry and Organocatalysis
© Georg Thieme Verlag Stuttgart · New York

Serum Albumins Host Copper-Catalyzed Diels-Alder Reactions

Contributor(s): Benjamin List, Michael Stadler
M. T. Reetz*, N. Jiao
Max-Planck-Institut für Kohlenforschung, Mülheim/Ruhr, Germany
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Publication History

Publication Date:
21 April 2006 (online)

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Significance

Protein conjugates of serum albumins and phthalocyanine-copper (II) complexes are shown to mediate Diels-Alder reactions with high endo/exo and enantioselectivities. The catalysts were found to work best under conditions of a formate buffer at pH 4. Several commercially available albumins have been tested, with bovine serum albumin (BSA) giving the best results. The use of copper(II) precursors other than phthalocyanine (i.e. CuCl2) led to dramatic loss of enantio­selectivity, which is reasoned to originate from diminished bond strength to the protein. Moreover, the phthalocyanine was found to be the source of the good endo selectivities.