Improving Physical Properties via CH Oxidation: Chemical and Enzymatic Approaches Academic Article uri icon

abstract

  • AbstractPhysicochemical properties constitute a key factor for the success of a drug candidate. Whereas many strategies to improve the physicochemical properties of small heterocycletype leads exist, complex hydrocarbon skeletons are more challenging to derivatize because of the absence of functional groups. A variety of CH oxidation methods have been explored on the betulin skeleton to improve the solubility of this very bioactive, yet poorly watersoluble, natural product. Capitalizing on the innate reactivity of the molecule, as well as the few molecular handles present on the core, allowed oxidations at different positions across the pentacyclic structure. Enzymatic oxidations afforded several orthogonal oxidations to chemical methods. Solubility measurements showed an enhancement for many of the synthesized compounds.

published proceedings

  • Angewandte Chemie

author list (cited authors)

  • Michaudel, Q., Journot, G., RegueiroRen, A., Goswami, A., Guo, Z., Tully, T. P., ... Baran, P. S.

citation count

  • 13

complete list of authors

  • Michaudel, Quentin||Journot, Guillaume||Regueiro‚ÄźRen, Alicia||Goswami, Animesh||Guo, Zhiwei||Tully, Thomas P||Zou, Lufeng||Ramabhadran, Raghunath O||Houk, Kendall N||Baran, Phil S

publication date

  • November 2014

publisher