Remote Desymmetrization at Near-Nanometer Group Separation Catalyzed by a Miniaturized Enzyme Mimic

• Published in: Journal of the American Chemical Society Vol. 128; no. 51; pp. 16454 - 16455
• Main Authors: Lewis, Chad A, Chiu, Anna, Kubryk, Michele, Balsells, Jaume, Pollard, David, Esser, Craig K, Murry, Jerry, Reamer, Robert A, Hansen, Karl B, Miller, Scott J
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 27.12.2006; Amer Chemical Soc
• Subjects: Biphenyl Compounds - chemical synthesis; Biphenyl Compounds - chemistry; Catalysis; Chemistry; Chemistry, Multidisciplinary; Enzymes - chemistry; Exact sciences and technology; General and physical chemistry; Magnetic Resonance Spectroscopy; Molecular Conformation; Peptides - chemistry; Physical Sciences; Science & Technology; Sensitivity and Specificity; Stereoisomerism; ORGANIC-SYNTHESIS; SELECTIVITY; INDUCTION; Nanometer scale; Catalytic reaction; Separation; Biomimetics; Enzyme
• ISSN: 0002-7863; 1520-5126
• DOI: 10.1021/ja067840j

The chirality of biological receptors often requires syntheses of therapeutic compounds in single enantiomer form. The field of asymmetric catalysis addresses enantioselective synthesis with chiral catalysts. Chemical differentiation of sites within molecules that are separated in space by long distances presents special challenges to chiral catalysts. As the distance between enantiotopic sites increases within a substrate, so too may the requirements for size and complexity for the catalyst. The extreme of catalyst complexity could be defined by macromolecular enzymes and their amazing capacity to effect stereospecific reactions over long distances between reactive sites and enzyme−substrate contacts. We report here a synthetic, miniaturized enzyme mimic that catalyzes a desymmetrization reaction over a very long distance.