2010
DOI: 10.1074/jbc.m110.159152
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Chemoenzymatic Design of Heparan Sulfate Oligosaccharides*

Abstract: Heparan sulfate is a sulfated glycan that exhibits essential physiological functions. Interrogation of the specificity of heparan sulfate-mediated activities demands a library of structurally defined oligosaccharides. Chemical synthesis of large heparan sulfate oligosaccharides remains challenging. We report the synthesis of oligosaccharides with different sulfation patterns and sizes from a disaccharide building block using glycosyltransferases, heparan sulfate C 5 -epimerase, and sulfotransferases. This meth… Show more

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Cited by 148 publications
(197 citation statements)
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“…To date, it has been difficult to unambiguously assign the mode of action of heparanase. Recently, we reported an advanced chemoenzymatic method to synthesize HS oligosaccharides with high efficiency and purity (13,14). This method allowed us to prepare structurally defined oligosaccharide substrates to probe heparanase.…”
mentioning
confidence: 99%
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“…To date, it has been difficult to unambiguously assign the mode of action of heparanase. Recently, we reported an advanced chemoenzymatic method to synthesize HS oligosaccharides with high efficiency and purity (13,14). This method allowed us to prepare structurally defined oligosaccharide substrates to probe heparanase.…”
mentioning
confidence: 99%
“…The Penta-1 backbone with the structure GlcUA-N-trifluoroacetylglucosamine (GlcNTFA)-GlcUA-GlcNTFA-GlcUA-pNP was prepared using a previously described method (13). Briefly, GlcUA-pNP was incubated with a UDP-monosaccharide donor (UDP-GlcNAc, UDP-GlcNTFA, or UDP-GlcUA) and bacterial glycosyltransferase (KfiA or Pasteurella multocida heparosan synthase 2) in buffer containing 25 mM Tris-HCl (pH 7.2) and 10 mM MnCl 2 .…”
mentioning
confidence: 99%
“…Useful unnatural donors, such as UDP-N-trifluoroacetylglucosamine (UDP-GlcNTFA) and UDP-N-t-Boc-glucosamine (UDP-GlcNtBoc), are accepted as substrates for some bacterial glycosyltransferases. The advantage of these unnatural donors is that the residues can be used as temporary protecting groups, as chemical tags, or as foundations for further modifications before their selective removal under mild base or acid conditions, respectively (Liu et al 2010;DeAngelis et al 2013). …”
Section: Donorsmentioning
confidence: 99%
“…One commonly used acceptor, a disaccharide with a reducing end anhydromannitol residue, is conveniently prepared from bacterial polysaccharide (Liu et al 2010; Fig. 1 Chemoenzymatic synthesis of low molecular weight heparins.…”
Section: Acceptorsmentioning
confidence: 99%
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