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Chemoenzymatic Synthesis of Oligohyaluronan–Lipid Conjugates

[Image: see text] Herein, we describe an efficient and high-yielding method to synthesize hyaluronan oligosaccharide–lipid conjugates. This strategy is based on first covalently attaching diphytanoyl glycerophosphatidylethanolamine (DiPhPE) to commercially available high molecular weight hyaluronic...

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Autores principales: Ruhela, Dipali, Kivimäe, Saul, Szoka, Francis C.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3993934/
https://www.ncbi.nlm.nih.gov/pubmed/24646444
http://dx.doi.org/10.1021/bc4005975
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author Ruhela, Dipali
Kivimäe, Saul
Szoka, Francis C.
author_facet Ruhela, Dipali
Kivimäe, Saul
Szoka, Francis C.
author_sort Ruhela, Dipali
collection PubMed
description [Image: see text] Herein, we describe an efficient and high-yielding method to synthesize hyaluronan oligosaccharide–lipid conjugates. This strategy is based on first covalently attaching diphytanoyl glycerophosphatidylethanolamine (DiPhPE) to commercially available high molecular weight hyaluronic acid (HA), via the carboxylate group of the glucuronic acid using carbodiimide chemistry. The HA-lipid conjugate mixture is then digested with bovine testicular hyaluronidase to yield HA-DiPhPE conjugates that have a narrow distribution of moderately sized HA oligosaccharides. These HA-lipid conjugates can be incorporated into liposomes or micelles to selectively target CD44 that is overexpressed on many cancer or cancer initiating cells.
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spelling pubmed-39939342015-03-19 Chemoenzymatic Synthesis of Oligohyaluronan–Lipid Conjugates Ruhela, Dipali Kivimäe, Saul Szoka, Francis C. Bioconjug Chem [Image: see text] Herein, we describe an efficient and high-yielding method to synthesize hyaluronan oligosaccharide–lipid conjugates. This strategy is based on first covalently attaching diphytanoyl glycerophosphatidylethanolamine (DiPhPE) to commercially available high molecular weight hyaluronic acid (HA), via the carboxylate group of the glucuronic acid using carbodiimide chemistry. The HA-lipid conjugate mixture is then digested with bovine testicular hyaluronidase to yield HA-DiPhPE conjugates that have a narrow distribution of moderately sized HA oligosaccharides. These HA-lipid conjugates can be incorporated into liposomes or micelles to selectively target CD44 that is overexpressed on many cancer or cancer initiating cells. American Chemical Society 2014-03-19 2014-04-16 /pmc/articles/PMC3993934/ /pubmed/24646444 http://dx.doi.org/10.1021/bc4005975 Text en Copyright © 2014 American Chemical Society
spellingShingle Ruhela, Dipali
Kivimäe, Saul
Szoka, Francis C.
Chemoenzymatic Synthesis of Oligohyaluronan–Lipid Conjugates
title Chemoenzymatic Synthesis of Oligohyaluronan–Lipid Conjugates
title_full Chemoenzymatic Synthesis of Oligohyaluronan–Lipid Conjugates
title_fullStr Chemoenzymatic Synthesis of Oligohyaluronan–Lipid Conjugates
title_full_unstemmed Chemoenzymatic Synthesis of Oligohyaluronan–Lipid Conjugates
title_short Chemoenzymatic Synthesis of Oligohyaluronan–Lipid Conjugates
title_sort chemoenzymatic synthesis of oligohyaluronan–lipid conjugates
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3993934/
https://www.ncbi.nlm.nih.gov/pubmed/24646444
http://dx.doi.org/10.1021/bc4005975
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