title: Synthesis and structural characterization of three unique Helicobacter pylori α-cholesteryl phosphatidyl glucosides.
abstract: 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.
authors.affiliation: Department of Chemistry, University of California, Davis, One Shields Ave, Davis, CA 95616 (USA).
authors.forename: Huy Q
authors.initials: HQ
authors.lastname: Nguyen
authors.forename: Ryan A
authors.initials: RA
authors.lastname: Davis
authors.forename: Jacquelyn
authors.initials: J
authors.lastname: Gervay-Hague
mesh_terms: D060326:Chemistry Techniques, Synthetic; D002784:Cholesterol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D016481:Helicobacter Infections / Q000382:microbiology; D016480:Helicobacter pylori / Q000737:chemistry*; D006801:Humans; D007155:Immunologic Factors / Q000138:chemical synthesis / Q000737:chemistry*; D010766:Phosphorylation
chemical_list: D007155:Immunologic Factors; C027578:cholesteryl glucoside; D002784:Cholesterol
keywords: glycosyl iodide; immunomodulator; phosphorylation; steroids; total synthesis