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

Davis, Ryan A.; Lin, Chun-Hung; Gervay-Hague, Jacquelyn

doi:10.1039/c2cc33948j

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

Aug 02 2012
By Davis, Ryan A. ; Lin, Chun-Hung ; Gervay-Hague, Jacquelyn
http://dx.doi.org/10.1039/c2cc33948j
Source: Chem Commun (Camb). 48(72):9083-9085.

[PDF-607.75 KB]

English

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Details:

Alternative Title:

Chem Commun (Camb)
Personal Author:

Davis, Ryan A. ; Lin, Chun-Hung ; Gervay-Hague, Jacquelyn

Davis, Ryan A. ; Lin, Chun-Hung ; Gervay-Hague, Jacquelyn Less -
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

PR1973/PR/OCPHP CDC HHS/United States ; R01 GM090262/GM/NIGMS NIH HHS/United States ; R01GM090262/GM/NIGMS NIH HHS/United States Less -
Collection(s):

CDC Public Access
Main Document Checksum:

[+]

urn:sha256:6d697d954ed26f6c38df07bc96fc18bd8c2f61589e08f9e0dab1459c48064b8e
Download URL:

https://stacks.cdc.gov/view/cdc/33722/cdc_33722_DS1.pdf
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