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Synthesis and structural characterization of three unique Helicobacter pylori ?-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-?-D-glucopyranosides (?CPG) unique to Helicobacter pylori have been achieved. The approach relies upon regioselective deprotection of per-O-trimethylsilyl-?-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.

SUBMITTER: Nguyen HQ 

PROVIDER: S-EPMC4319363 | biostudies-literature | 2014 Dec

REPOSITORIES: biostudies-literature

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Synthesis and structural characterization of three unique Helicobacter pylori α-cholesteryl phosphatidyl glucosides.

Nguyen Huy Q HQ   Davis Ryan A RA   Gervay-Hague Jacquelyn J  

Angewandte Chemie (International ed. in English) 20140904 49


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 cy  ...[more]

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