Step-economy synthesis of β-steryl sialosides using a sialyl iodide donor-Reference-Cited by-同舟云学术

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Step-economy synthesis of β-steryl sialosides using a sialyl iodide donor

Published:2019-03-19 Issue:6 Volume:72 Page:449-460
ISSN:0021-8820
Container-title:The Journal of Antibiotics
language:en
Short-container-title:J Antibiot

Author:

Park Simon S.^ORCID,Gervay-Hague Jacquelyn^ORCID

Funder

NSF | Directorate for Mathematical & Physical Sciences | Division of Chemistry

NSF | Directorate for Mathematical & Physical Sciences | Division of Materials Research

U.S. Department of Health & Human Services | NIH | National Institute of General Medical Sciences

Publisher

Springer Science and Business Media LLC

Subject

Drug Discovery,Pharmacology

Link

http://www.nature.com/articles/s41429-019-0165-0.pdf

Reference38 articles.

1. Davis RA, Lin C-H, Gervay-Hague J. Chemoenzymatic synthesis of cholesteryl-6-O-tetradecanoyl-[small alpha]-d-glucopyranoside: a product of host cholesterol efflux promoted by Helicobacter pylori. Chem Commun. 2012;48:9083–5. https://doi.org/10.1039/C2CC33948J

2. Davis RA, Fettinger JC, Gervay-Hague J. Tandem glycosyl iodide glycosylation and regioselective enzymatic acylation affords 6-O-tetradecanoyl-α-d-cholesterylglycosides. J Org Chem. 2014;79:8447–52. https://doi.org/10.1021/jo501371h

3. Nguyen HQ, Davis RA, Gervay-Hague J. Synthesis and structural characterization of three unique Helicobacter pylori α-cholesteryl phosphatidyl glucosides. Angew Chem Int Ed. 2014;126:1–5. https://doi.org/10.1002/ange.201406529

4. Jan H-M, et al. Metabolic labelling of cholesteryl glucosides in Helicobacter pylori reveals how the uptake of human lipids enhances bacterial virulence. Chem Sci. 2016;7:6208–16. https://doi.org/10.1039/C6SC00889E

5. Grille S, Zaslawski A, Thiele S, Plat J, Warnecke D. The functions of steryl glycosides come to those who wait: Recent advances in plants, fungi, bacteria and animals. Prog Lipid Res. 2010;49:262–88. https://doi.org/10.1016/j.plipres.2010.02.001

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1. Synthesis of sialyl halides with various acyl protective groups;Carbohydrate Research;2024-02

2. The first example of unpromoted sialylation of a secondary alcohol;Russian Chemical Bulletin;2022-09

3. Synthesis and Glycosidation of Anomeric Halides: Evolution from Early Studies to Modern Methods of the 21st Century;Chemical Reviews;2022-06-08

4. Donor‐Reactivity‐Controlled Sialylation Reactions;European Journal of Organic Chemistry;2021-08-06

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