Solid-Phase Synthesis of Multivalent Glycoconjugates on a DNA Synthesizer

Dubber, Michael; Fréchet, Jean M. J.

doi:10.1021/bc0256244

Cited by 47 publications

(40 citation statements)

References 27 publications

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“…The method is inspired by the synthesis of biological polymers, since phosphoramidite chemistry was applied . Moreover, phosphoramidite chemistry was already described for the synthesis of oligopyrenotides, glycoconjugates and oligonucleotide‐oligospermine conjugates appended to DNA . In the work of Sleiman, Serpell and co‐workers, oligonucleotides that contain 19 nucleotides were firstly synthesized on a solid support using automated processes .…”

Section: Solid‐phase Synthesis Of Sequence‐defined Macromoleculesmentioning

confidence: 99%

Recent Progress in the Design of Monodisperse, Sequence-Defined Macromolecules

Solleder

Schneider

Wetzel

et al. 2017

Macromol. Rapid Commun.

181

173

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This review describes different synthetic strategies towards sequence-defined, monodisperse macromolecules, which are built up by iterative approaches and lead to linear non-natural polymer structures. The review is divided in three parts: solution phase-, solid phase-, and fluorous- and polymer-tethered approaches. Moreover, synthesis procedures leading to conjugated and non-conjugated macromolecules are considered and discussed in the respective sections. A major focus in the evaluation is the applicability of the different approaches in polymer chemistry. In this context, simple procedures for monomer and oligomer synthesis, overall yields, scalability, purity of the oligomers, and the achievable level of control (side-chains, backbone, stereochemistry) are important benchmarks.

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Section: Solid‐phase Synthesis Of Sequence‐defined Macromoleculesmentioning

confidence: 99%

Recent Progress in the Design of Monodisperse, Sequence-Defined Macromolecules

Solleder

Schneider

Wetzel

et al. 2017

Macromol. Rapid Commun.

181

173

View full text Add to dashboard Cite

show abstract

“…However, these monomers are used, in general, for oligonucleotide modification rather than for preparing synthetic polymers. [38][39][40][41][42][43] Ganesan and coworker have reported the synthesis of peptidomimetic polyphosphates using phosphoramidite chemistry. 44 Häner and coworkers have described the solid-phase phosphoramidite synthesis of oligopyrenotides.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Non-Natural Sequence-Encoded Polymers Using Phosphoramidite Chemistry

2015

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Sequence-defined non-natural polyphosphates were prepared using iterative phosphoramidite protocols on a polystyrene solid support. Three monomers were used in this work: 2-cyanoethyl (3-dimethoxytrityloxy-propyl) diisopropylphosphoramidite (0), 2-cyanoethyl (3-dimethoxytrityloxy-2,2-dimethyl-propyl) diisopropylphosphoramidite (1), and 2-cyanoethyl (3-dimethoxytrityloxy-2,2-dipropargyl-propyl) diisopropylphosphoramidite (1'). Phosphoramidite coupling steps allowed rapid synthesis of homopolymers and copolymers. In particular, the comonomers (0, 1), (0, 1'), and (1, 1') were used to synthesize sequence-encoded copolymers. It was found that long encoded sequences could be easily built using phosphoramidite chemistry. ESI-HRMS, MALDI-HRMS, NMR, and size exclusion chromatography analyses indicated the formation of monodisperse polymers with controlled comonomer sequences. The polymers obtained with the comonomers (0, 1') and (1, 1') were also modified by copper-catalyzed azide-alkyne cycloaddition with a model azide compound, namely 11-azido-3,6,9-trioxaundecan-1-amine. (1)H and (13)C NMR analysis evidenced quantitative modification of the alkyne side-chains of the monodisperse copolymers. Thus, the molecular structure of the coding monomer units can be easily varied after polymerization. Altogether, the present results open up interesting avenues for the design of information-containing macromolecules.

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“…These variations allowed, for example, to mimic effectively the HIV-1 gp120 surface for binding human HIV-1 antibody [70] (Scheme 6) or to inhibit inducible nitric oxide synthase. [71] Other synthetic efforts have focused on the formation of heterofunctionalized saccharide shells in the glycodendrimers. In particular, the coupling of at least two different saccharide units or of one saccharide unit with other water-soluble functional groups has been described to enhance the binding affinity to lectins, [51] and the influence of the density of the saccharide shell on binding affinities [51,72] has been evaluated in this regard.…”

Section: Thiol-ene 13-dipolar Cycloaddition and Others (Scheme 5)mentioning

confidence: 99%

Glycopolymers of Various Architectures—More than Mimicking Nature

Voit

Appelhans

2010

Macro Chemistry & Physics

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Carbohydrates have a highly important role in biological functions. The increasing understanding of their biological interactions has also triggered a strongly increased interest in the preparation of synthetic glycopolymers of various architectures and well‐defined structure which can mimic biological functions in a less complex environment. In the last few years synthetic approaches in polymer science have been refined and newly developed in order to achieve complex carbohydrate architectures and to make use of them in various areas like glycomics, biotechnology, biosensors, and medicine. Besides the use of especially controlled radical polymerization techniques, highly efficient polymer analogous reactions that can be carried out in aqueous media have been developed and applied to linear and dendritic macromolecules. Self assembly aspects and their effectiveness in biological functions have been assessed.

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Solid-Phase Synthesis of Multivalent Glycoconjugates on a DNA Synthesizer

Cited by 47 publications

References 27 publications

Recent Progress in the Design of Monodisperse, Sequence-Defined Macromolecules

Recent Progress in the Design of Monodisperse, Sequence-Defined Macromolecules

Synthesis of Non-Natural Sequence-Encoded Polymers Using Phosphoramidite Chemistry

Glycopolymers of Various Architectures—More than Mimicking Nature

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