Fluorous-Assisted Chemoenzymatic Synthesis of Heparan Sulfate Oligosaccharides

[Image: see text] The chemoenzymatic synthesis of heparan sulfate tetrasaccharide (1) and hexasaccharide (2) with a fluorous tag attached at the reducing end is reported. The fluorous tert-butyl dicarbonate ((F)Boc) tag did not interfere with enzymatic recognition for both elongation and specific su...

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Autores principales: Cai, Chao, Dickinson, Demetria M., Li, Lingyun, Masuko, Sayaka, Suflita, Matt, Schultz, Victor, Nelson, Shawn D., Bhaskar, Ujjwal, Liu, Jian, Linhardt, Robert J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3998769/
https://www.ncbi.nlm.nih.gov/pubmed/24697306
http://dx.doi.org/10.1021/ol500738g
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author Cai, Chao
Dickinson, Demetria M.
Li, Lingyun
Masuko, Sayaka
Suflita, Matt
Schultz, Victor
Nelson, Shawn D.
Bhaskar, Ujjwal
Liu, Jian
Linhardt, Robert J.
author_facet Cai, Chao
Dickinson, Demetria M.
Li, Lingyun
Masuko, Sayaka
Suflita, Matt
Schultz, Victor
Nelson, Shawn D.
Bhaskar, Ujjwal
Liu, Jian
Linhardt, Robert J.
author_sort Cai, Chao
collection PubMed
description [Image: see text] The chemoenzymatic synthesis of heparan sulfate tetrasaccharide (1) and hexasaccharide (2) with a fluorous tag attached at the reducing end is reported. The fluorous tert-butyl dicarbonate ((F)Boc) tag did not interfere with enzymatic recognition for both elongation and specific sulfation, and flash purification was performed by standard fluorous solid-phase extraction (FSPE). Based on an (F)Boc attached disaccharide as acceptor, a series of partial N-sulfated, 6-O-sulfated heparan sulfate oligosaccharides were successfully synthesized employing fluorous techniques.
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spelling pubmed-39987692015-04-04 Fluorous-Assisted Chemoenzymatic Synthesis of Heparan Sulfate Oligosaccharides Cai, Chao Dickinson, Demetria M. Li, Lingyun Masuko, Sayaka Suflita, Matt Schultz, Victor Nelson, Shawn D. Bhaskar, Ujjwal Liu, Jian Linhardt, Robert J. Org Lett [Image: see text] The chemoenzymatic synthesis of heparan sulfate tetrasaccharide (1) and hexasaccharide (2) with a fluorous tag attached at the reducing end is reported. The fluorous tert-butyl dicarbonate ((F)Boc) tag did not interfere with enzymatic recognition for both elongation and specific sulfation, and flash purification was performed by standard fluorous solid-phase extraction (FSPE). Based on an (F)Boc attached disaccharide as acceptor, a series of partial N-sulfated, 6-O-sulfated heparan sulfate oligosaccharides were successfully synthesized employing fluorous techniques. American Chemical Society 2014-04-04 2014-04-18 /pmc/articles/PMC3998769/ /pubmed/24697306 http://dx.doi.org/10.1021/ol500738g Text en Copyright © 2014 American Chemical Society
spellingShingle Cai, Chao
Dickinson, Demetria M.
Li, Lingyun
Masuko, Sayaka
Suflita, Matt
Schultz, Victor
Nelson, Shawn D.
Bhaskar, Ujjwal
Liu, Jian
Linhardt, Robert J.
Fluorous-Assisted Chemoenzymatic Synthesis of Heparan Sulfate Oligosaccharides
title Fluorous-Assisted Chemoenzymatic Synthesis of Heparan Sulfate Oligosaccharides
title_full Fluorous-Assisted Chemoenzymatic Synthesis of Heparan Sulfate Oligosaccharides
title_fullStr Fluorous-Assisted Chemoenzymatic Synthesis of Heparan Sulfate Oligosaccharides
title_full_unstemmed Fluorous-Assisted Chemoenzymatic Synthesis of Heparan Sulfate Oligosaccharides
title_short Fluorous-Assisted Chemoenzymatic Synthesis of Heparan Sulfate Oligosaccharides
title_sort fluorous-assisted chemoenzymatic synthesis of heparan sulfate oligosaccharides
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3998769/
https://www.ncbi.nlm.nih.gov/pubmed/24697306
http://dx.doi.org/10.1021/ol500738g
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