Abstract
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.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 9083-9085 |
| Number of pages | 3 |
| Journal | Chemical Communications |
| Volume | 48 |
| Issue number | 72 |
| DOIs | |
| State | Published - Sep 18 2012 |
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ASJC Scopus subject areas
- Metals and Alloys
- Materials Chemistry
- Surfaces, Coatings and Films
- Electronic, Optical and Magnetic Materials
- Ceramics and Composites
- Catalysis
- Chemistry(all)
Cite this
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.
In: Chemical Communications, Vol. 48, No. 72, 18.09.2012, p. 9083-9085.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Chemoenzymatic synthesis of cholesteryl-6-O-tetradecanoyl-α-d- glucopyranoside
T2 - A product of host cholesterol efflux promoted by Helicobacter pylori
AU - Davis, Ryan A.
AU - Lin, Chun Hung
AU - Gervay-Hague, Jacquelyn
PY - 2012/9/18
Y1 - 2012/9/18
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=84865042241&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84865042241&partnerID=8YFLogxK
U2 - 10.1039/c2cc33948j
DO - 10.1039/c2cc33948j
M3 - Article
C2 - 22854787
AN - SCOPUS:84865042241
VL - 48
SP - 9083
EP - 9085
JO - Chemical Communications
JF - Chemical Communications
SN - 1359-7345
IS - 72
ER -