Structural Studies of a Cinchona Alkaloid Catalyst

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dc.contributor.advisor Petsko, Gregory Travis, Sophie 2013-05-21T14:52:02Z 2013-05-21T14:52:02Z 2013
dc.description.abstract Cinchona alkaloid catalysts are responsible for the highly enantioselective catalysis of over one hundred classes of reaction (1). It is believed that the key to understanding this enantioselectivity lies in determining the solution conformation and mechanism of the catalyst; however, molecular modeling and NMR studies have identified four energy minima, each of which is a candidate for the active conformation, and the mechanism is currently uncertain. This study reports the three-dimensional structure of Q-7, a quinine derivative responsible for the highly enantioselective isomerization of γ-substituted α,β-unsaturated butenolides (2), in complex with tetragonal hen egg white lysozyme at 1.8 Å resolution. This atomic-resolution structure of the catalyst is suggestive as to the active conformation of Q-7 and represents a new system that may allow visualization of the catalyst-reactant complex for this and many other organic catalysts of unknown structure and mechanism. Progress has also been made toward obtaining a ternary structure with both Q-7 and its substrate, and preliminary data suggest that Q-7’s catalytic activity is not abolished by coordination to lysozyme.
dc.description.sponsorship Brandeis University, Graduate School of Arts and Sciences
dc.format.mimetype application/pdf
dc.language English
dc.language.iso eng
dc.publisher Brandeis University
dc.relation.ispartofseries Brandeis University Theses and Dissertations
dc.rights Copyright by Sophie Travis 2013
dc.title Structural Studies of a Cinchona Alkaloid Catalyst
dc.type Thesis
dc.contributor.department Department of Biochemistry MS Masters Biochemistry Brandeis University, Graduate School of Arts and Sciences

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