Synthesis and Structural Characterization of Three Unique Helicobacter pylori α-Cholesteryl phosphatidyl glucosides

Details

• Alternative Title:
  Angew Chem Int Ed Engl
• Personal Author:
  Nguyen, Huy Q. ; Davis, Ryan A. ; Gervay-Hague, Jacquelyn
• Description:
  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.
• Keywords:
  Chemistry Techniques, Synthetic Cholesterol Glycosyl Iodide Helicobacter Infections Helicobacter Pylori Humans Immunologic Factors Immunomodulator Phosphorylation Total Synthesis
• Source:
  Angew Chem Int Ed Engl. 53(49):13400-13403
• Pubmed ID:
  25195783
• Pubmed Central ID:
  PMC4319363
• Document Type:
  Journal Article
• Funding:
  R01 GM090262/GM/NIGMS NIH HHSUnited States/ ; R01GM090262/GM/NIGMS NIH HHSUnited States/ ; PR1973/PR/OCPHP CDC HHSUnited States/
• Volume:
  53
• Issue:
  49
• Collection(s):
  CDC Public Access
• Main Document Checksum:
  urn:sha256:61d25cb52e076b7a0e4df9dc1581b64beadd5ca65770a6a5fea3396215d7327b
• Download URL:
  https://stacks.cdc.gov/view/cdc/30279/cdc_30279_DS1.pdf
• File Type:
  [PDF - 834.10 KB ]