Substrate analog studies of the ω-regiospecificity of Mycobacterium tuberculosis cholesterol metabolizing cytochrome P450 enzymes CYP124A1, CYP125A1 and …

…, S Chow, JJ De Voss, PRO de Montellano

Index: Johnston, Jonathan B.; Singh, Arti A.; Clary, Anaelle A.; Chen, Chiung-Kuan; Hayes, Patricia Y.; Chow, Sharon; De Voss, James J.; Ortiz De Montellano, Paul R. Bioorganic and Medicinal Chemistry, 2012 ,  vol. 20,  # 13  p. 4064 - 4081

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Citation Number: 10

Abstract

We report the synthesis and evaluation of a series of cholesterol side-chain analogs as mechanistic probes of three important Mycobacterium tuberculosis cytochrome P450 enzymes that selectively oxidize the ω-position of the methyl-branched cholesterol side- chain. To probe the structural requirements for the thermodynamically disfavored ω- regiospecificity we compared the binding of these substrate analogs to each P450, ...