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Tandem Glycosyl Iodide Glycosylation and Regioselective Enzymatic Acylation Affords 6-O-Tetradecanoyl-α-d-cholesterylglycosides
[Image: see text] A generalized synthesis of α-d-cholesterylglycosides has been achieved using one-pot per-O-trimethylsilyl glycosyl iodide glycosidation. Both cholesteryl α-d-glucopyranoside (αCG) and cholesteryl α-d-galactopyranoside were prepared in high yield. These compounds were further esteri...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical
Society
2014
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4156253/ https://www.ncbi.nlm.nih.gov/pubmed/25093454 http://dx.doi.org/10.1021/jo501371h |
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author | Davis, Ryan A. Fettinger, James C. Gervay-Hague, Jacquelyn |
author_facet | Davis, Ryan A. Fettinger, James C. Gervay-Hague, Jacquelyn |
author_sort | Davis, Ryan A. |
collection | PubMed |
description | [Image: see text] A generalized synthesis of α-d-cholesterylglycosides has been achieved using one-pot per-O-trimethylsilyl glycosyl iodide glycosidation. Both cholesteryl α-d-glucopyranoside (αCG) and cholesteryl α-d-galactopyranoside were prepared in high yield. These compounds were further esterified using regioselective enzymatic acylation with tetradecanoyl vinyl ester to afford 6-O-tetradecanoyl-α-d-cholesteryl glucopyranoside (αCAG) of Helicobacter pylori and the corresponding galactose analogue in 66–78% overall yields from free sugars. The tandem step-economy sequence provides novel analogues to facilitate glycolipidomic profiling. |
format | Online Article Text |
id | pubmed-4156253 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | American Chemical
Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-41562532015-08-05 Tandem Glycosyl Iodide Glycosylation and Regioselective Enzymatic Acylation Affords 6-O-Tetradecanoyl-α-d-cholesterylglycosides Davis, Ryan A. Fettinger, James C. Gervay-Hague, Jacquelyn J Org Chem [Image: see text] A generalized synthesis of α-d-cholesterylglycosides has been achieved using one-pot per-O-trimethylsilyl glycosyl iodide glycosidation. Both cholesteryl α-d-glucopyranoside (αCG) and cholesteryl α-d-galactopyranoside were prepared in high yield. These compounds were further esterified using regioselective enzymatic acylation with tetradecanoyl vinyl ester to afford 6-O-tetradecanoyl-α-d-cholesteryl glucopyranoside (αCAG) of Helicobacter pylori and the corresponding galactose analogue in 66–78% overall yields from free sugars. The tandem step-economy sequence provides novel analogues to facilitate glycolipidomic profiling. American Chemical Society 2014-08-05 2014-09-05 /pmc/articles/PMC4156253/ /pubmed/25093454 http://dx.doi.org/10.1021/jo501371h Text en Copyright © 2014 American Chemical Society Terms of Use (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) |
spellingShingle | Davis, Ryan A. Fettinger, James C. Gervay-Hague, Jacquelyn Tandem Glycosyl Iodide Glycosylation and Regioselective Enzymatic Acylation Affords 6-O-Tetradecanoyl-α-d-cholesterylglycosides |
title | Tandem Glycosyl Iodide Glycosylation
and Regioselective
Enzymatic Acylation Affords 6-O-Tetradecanoyl-α-d-cholesterylglycosides |
title_full | Tandem Glycosyl Iodide Glycosylation
and Regioselective
Enzymatic Acylation Affords 6-O-Tetradecanoyl-α-d-cholesterylglycosides |
title_fullStr | Tandem Glycosyl Iodide Glycosylation
and Regioselective
Enzymatic Acylation Affords 6-O-Tetradecanoyl-α-d-cholesterylglycosides |
title_full_unstemmed | Tandem Glycosyl Iodide Glycosylation
and Regioselective
Enzymatic Acylation Affords 6-O-Tetradecanoyl-α-d-cholesterylglycosides |
title_short | Tandem Glycosyl Iodide Glycosylation
and Regioselective
Enzymatic Acylation Affords 6-O-Tetradecanoyl-α-d-cholesterylglycosides |
title_sort | tandem glycosyl iodide glycosylation
and regioselective
enzymatic acylation affords 6-o-tetradecanoyl-α-d-cholesterylglycosides |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4156253/ https://www.ncbi.nlm.nih.gov/pubmed/25093454 http://dx.doi.org/10.1021/jo501371h |
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