Chemoenzymatic Synthesis of Cholesteryl-6-O-tetradecanoyl-α-D-glucopyranoside: A Product of Host Cholesterol Efflux Promoted by Helicobacter pylori

Details

• Alternative Title:
  Chem Commun (Camb)
• Personal Author:
  Davis, Ryan A. ; Lin, Chun-Hung ; Gervay-Hague, Jacquelyn
• Description:
  In a three-step protocol involving regioselective enzymatic acylation, per-O-trimethylsilylation, and a one-pot α-glycosidation-deprotection sequence, cholesteryl-6-O-tetradecanoyl-α-D-glucopyranoside (α-CAG) of Helicobacter pylori is afforded starting from glucose in an overall yield of 45%. The production of CAG can be scaled to make purified quantities available to the biological community for the first time.
• Subjects:
  Biological Transport Chemistry Techniques, Synthetic Cholesterol Fungal Proteins Glycolipids Helicobacter Pylori Lipase Saponins Stereoisomerism Substrate Specificity
• Source:
  Chem Commun (Camb). 48(72):9083-9085.
• Pubmed ID:
  22854787
• Pubmed Central ID:
  PMC4271795
• Document Type:
  Journal Article
• Funding:
  PR1973/PR/OCPHP CDC HHS/United States ; R01 GM090262/GM/NIGMS NIH HHS/United States ; R01GM090262/GM/NIGMS NIH HHS/United States
• Volume:
  48
• Issue:
  72
• Collection(s):
  CDC Public Access
• Main Document Checksum:
  urn:sha256:6d697d954ed26f6c38df07bc96fc18bd8c2f61589e08f9e0dab1459c48064b8e
• Download URL:
  https://stacks.cdc.gov/view/cdc/33722/cdc_33722_DS1.pdf
• File Type:
  [PDF - 607.75 KB ]