Synthesis of Nitric Oxide Reductase Active Site Models Bearing Key Components at Both Distal and Proximal Sites

Org. Lett., 9 (15), 2855 -2858, 2007. 10.1021/ol071007p S1523-7060(07)01007-3
Web Release Date: June 20, 2007

Synthesis of Nitric Oxide Reductase Active Site Models Bearing Key Components at Both Distal and Proximal Sites

James P. Collman,* Ying Yang, and Richard A. Decréau

Department of Chemistry, Stanford University, Stanford, California 94305-5080

jpc@stanford.edu

Received April 30, 2007

Abstract:

Porphyrins 1ab and 2ab were successfully synthesized from cis-

₂-bisimidazole-

-imidazole-tail porphyrins and two newly synthesized imidazole pickets containing an aliphatic ester chain following a [2+1] approach. The four compounds possess a distal trisimidazole set, a distal carboxylic acid, and a proximal imidazole, which constitute all the key features of the coordination environment of the active site in Bacterial Nitric Oxide Reductase (NOR) and make them the closest synthetic NOR model ligands to date.

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