Phosphorylation:

Phosphates are a ubiquitous functional group within biological systems that are incorporated in critical molecules such as DNA, RNA, proteins and small molecule messengers such as ATP and inositol phosphates.  The development of new and more efficient methods for forming phosphorylated compounds can impact the treatment of diseases where phosphorylation is aberrant (such as cancer), initiate the use of phosphorylated small molecules in disease treatment and answer fundamental questions about the nature of this chemical structure.

Research in my group focuses on the development of new methods to phosphorylate alcohols utilizing both phosphorous (III) and phosphorous (V) reagents. Current limitations in these reactions include non-catalyzed pathways, poor protecting groups on phosphorous and harsh reaction conditions.

Phosphorous (III):

Currently, phosphorous (III) reactions require an excess of tetrazole or dicyanoimidazole (the catalyst). We will work on methods to regenerate the catalyst during the course of the reaction so a substoichiometric amount of the catalyst can be used. This will be beneficial in conducting asymmetric phosphorlyation and provide "greener" reaction conditions, since tetrazoles are toxic and explosive.

Phosphorous (V):

Many phosphorous (v) reagents are unreactive towards nucleophilic catalysis or provide poor protecting groups on phosphorous. When the common benzyl protecting group is used, attack of the nucleophilic catalyst takes place at the benzylic carbon and NOT the phosphorous center. By changing the sterics and electronics of the protecting groups on phosphorous, hopefully new phosphorous reagents will be identified that allow for nucleophilic catalysis and ease of deprotection.