Bachelor of Science, University of Washington (2008)
Doctor of Philosophy, University of California Davis (2014)
Polly Fordyce, Postdoctoral Faculty Sponsor
View details for DOI 10.1002/adom.201600548
Steryl glycosides produced by bacteria play important biological roles in the evasion and modulation of host immunity. Step-economical syntheses of three cholesteryl-6-O-phosphatidyl-α-D-glucopyranosides (αCPG) unique to Helicobacter pylori have been achieved. The approach relies upon regioselective deprotection of per-O-trimethylsilyl-α-D-cholesterylglucoside at C6 followed by phosphoramidite coupling. Global TMS ether deprotection in the presence of oxygen and subsequent deprotection of the cyano ethyl phosphoester afforded the target compounds in 16-21 % overall yield starting from D-glucose. The structures of these natural products were determined using a combination of 2D NMR methods and mass spectrometry. These robust synthesis and characterization protocols provide analogues to facilitate glycolipidomic profiling and biological studies.
View details for DOI 10.1002/anie.201406529
View details for Web of Science ID 000345590300012
View details for PubMedID 25195783