Chemoenzymatic Synthesis of Oligohyaluronan–Lipid Conjugates

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...

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Bibliographic Details
Published inBioconjugate chemistry Vol. 25; no. 4; pp. 718 - 723
Main Authors Ruhela, Dipali, Kivimäe, Saul, Szoka, Francis C
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 16.04.2014
Subjects
Animals
Cancer
Carbohydrate Conformation
Carbohydrate Sequence
Cattle
Cells, Cultured
Cercopithecus aethiops
Chemistry
COS Cells
Enzymes
Hyaluronic Acid - biosynthesis
Hyaluronic Acid - chemistry
Hyaluronoglucosaminidase - metabolism
Lipids
Lipids - biosynthesis
Lipids - chemistry
Male
Molecular Sequence Data
Molecular weight
Oligosaccharides - biosynthesis
Oligosaccharides - chemistry
Testis - enzymology
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Summary: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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1043-1802
1520-4812
DOI:10.1021/bc4005975