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Improving physical properties via C-H oxidation: chemical and enzymatic approaches.


ABSTRACT: Physicochemical properties constitute a key factor for the success of a drug candidate. Whereas many strategies to improve the physicochemical properties of small heterocycle-type leads exist, complex hydrocarbon skeletons are more challenging to derivatize because of the absence of functional groups. A variety of C-H oxidation methods have been explored on the betulin skeleton to improve the solubility of this very bioactive, yet poorly water-soluble, 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.

SUBMITTER: Michaudel Q 

PROVIDER: S-EPMC4226272 | biostudies-literature | 2014 Nov

REPOSITORIES: biostudies-literature

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Improving physical properties via C-H oxidation: chemical and enzymatic approaches.

Michaudel Quentin Q   Journot Guillaume G   Regueiro-Ren Alicia A   Goswami Animesh A   Guo Zhiwei Z   Tully Thomas P TP   Zou Lufeng L   Ramabhadran Raghunath O RO   Houk Kendall N KN   Baran Phil S PS  

Angewandte Chemie (International ed. in English) 20140922 45


Physicochemical properties constitute a key factor for the success of a drug candidate. Whereas many strategies to improve the physicochemical properties of small heterocycle-type leads exist, complex hydrocarbon skeletons are more challenging to derivatize because of the absence of functional groups. A variety of C-H oxidation methods have been explored on the betulin skeleton to improve the solubility of this very bioactive, yet poorly water-soluble, natural product. Capitalizing on the innate  ...[more]

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