Synthesis and Structural Characterization of Three Unique Helicobacter pylori α‐Cholesteryl Phosphatidyl Glucosides1. Issue 49 (4th September 2014)

• Record Type: Journal Article
• Authors: Nguyen, Huy Q.; Davis, Ryan A.; Gervay‐Hague, Jacquelyn
• Is Part Of: Angewandte Chemie international edition. Volume 53:Issue 49(2014)
• Page Start: 13400
• Page End: 13403
• Publication Date: 2014-09-04
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201406529
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>Steryl glycosides produced by bacteria play important biological roles in the evasion and modulation of host immunity. Step‐economical syntheses of three cholesteryl‐6‐<italic>O</italic>‐phosphatidyl‐α‐<sc>D</sc>‐glucopyranosides (αCPG) unique to <italic>Helicobacter pylori</italic> have been achieved. The approach relies upon regioselective deprotection of per‐<italic>O</italic>‐trimethylsilyl‐α‐<sc>D</sc>‐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 <sc>D</sc>‐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.</p> </abstract>