Polymer-supported solution synthesis of heparan sulphate-like oligomers

Dreef-Tromp, C.M.; Willems, H.; Westerduin, Pieter; Veelen, Peter A. van; Boeckel, C. A. A. Van

doi:10.1016/s0960-894x(97)00183-2

Cited by 34 publications

(15 citation statements)

References 10 publications

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“…Since the pioneering synthesis of the antithrombin III binding heparin pentasaccharide, 18 several synthetic approaches for heparin have been described, [19][20][21][22][23][24][25][26][27][28][29][30][31] including polymer-supported strategies, [32][33][34][35] preactivation-based one-pot synthesis, 36 and reactivity-based one-pot synthesis. 37 Despite all these significant advances in the field, the synthesis of these molecules is still a challenging task.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of amine-functionalized heparin oligosaccharides for the investigation of carbohydrate–protein interactions in microtiter plates

et al. 2012

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The synthesis of well-defined oligosaccharides is crucial for the establishment of structure-activity relationships for specific sequences of heparin, contributing to the understanding of the biological role of this polysaccharide. It is highly convenient that the synthetic oligosaccharides contain an orthogonal functional group that allows selective conjugation of the probes and expands their use as chemical tools in glycobiology. We present here the synthesis of a series of amine-functionalized heparin oligosaccharides using an n+2 modular approach. The conditions of the glycosylation reactions were carefully optimized to produce efficiently the desired synthetic intermediates with an N-benzyloxycarbonyl-protected aminoethyl spacer at the reducing end. The use of microwave heating greatly facilitates O- and N-sulfation steps, avoiding experimental problems associated with these reactions. The synthesized oligosaccharides were immobilized in 384-well microtiter plates and successfully probed with a heparin-binding protein, the basic fibroblast growth factor FGF-2. The use of hexadecyltrimethylammonium bromide minimized the amount of sugar required for attachment to the solid support. Using this approach we quantified heparin-protein interactions, and surface dissociation constants for the synthetic heparin derivatives were determined.

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Section: Introductionmentioning

confidence: 99%

Synthesis of amine-functionalized heparin oligosaccharides for the investigation of carbohydrate–protein interactions in microtiter plates

et al. 2012

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“…The linear backbone of H/HS oligosaccharides should make them ideal candidates for the application of solid‐phase methodologies to their synthesis. Quite surprisingly, only one example has been reported in the literature 50. The authors used a polyethylene glycol (PEG) supported solution synthesis51,52 for the preparation of differently O ‐sulfated and O ‐methylated HS‐related oligosaccharides of various lengths, up to dodecasaccharides.…”

Section: Overview Of Synthetic Approaches Towards H/hs Fragmentsmentioning

confidence: 99%

Chemical Contributions to Understanding Heparin Activity: Synthesis of Related Sulfated Oligosaccharides

Poletti

Lay

2003

Eur J Org Chem

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Heparin and heparan sulfate are complex polysaccharides that modulate several biological events through the recognition of a number of distinct proteins. Chemical synthesis is a powerful tool to identify the unique binding domains responsible for the specific interactions and to generate potent analogues of the natural sequences. The present review reports the synthetic efforts of the last decade that are focused on the preparation of tailored fragments of these two polymers and analogues thereof. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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“…After cleavage from the linker the octasaccharide was obtained in good yield (overall 42%). Heparan sulfate-like oligomers have been prepared by polyethylene glycol monomethyl ether (MPEG)-supported solution-phase synthesis (Scheme 47) [200]. Glycosylation of the succinyl linked acceptor (linkage not via the anomeric position) was performed with the disaccharide trichloroacetimidate up to five times, again using the levulinoyl group as temporary protecting group.…”

Section: Solid-phase Synthesismentioning

confidence: 99%