Synthesis of AB4-type carbohydrate scaffolds as branching units in the glycosciences

Gloe, Tobias-Elias; Müller, Anne; Ciuk, Anna K.; Wrodnigg, Tanja

doi:10.1016/j.carres.2016.02.010

Cited by 6 publications

(3 citation statements)

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“…for the synthesis of carbohydrate‐centered glycoclusters . All carbohydrates have the advantage that their anomeric center can be easily distinguished from the other functional groups of the carbohydrate ring and therefore, free sugars can be converted into orthogonally functionalized glycosides of an AB 4 type, where “A“ represents an anomerically anchored functional group and “B“ represent the remaining sugar functionalities . AB 4 type carbohydrate platforms enable eventual immobilization of the compounds on surfaces or further conjugation and multimerization, respectively, through the orthogonal functional group “A“.…”

Section: Introductionmentioning

confidence: 99%

“…We and others have frequently employed carbohydrate scaffolds for the synthesis of multivalent glycomimetics in order to test homo‐ and heteromultivalency effects in carbohydrate recognition . In addition, we have recently started a project to control the spatial positioning and orientation of sugar ligands in order to test the influence of supramolecular 3D parameters in carbohydrate recognition.…”

Section: Introductionmentioning

confidence: 99%

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Carbohydrate‐Scaffolded Thymine Multimers: Scope and Limitations of the Allylation–Hydroboration Sequence

Ciuk

Gloe

2018

Eur J Org Chem

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Carbohydrates serve as versatile molecular scaffolds and platforms in organic chemistry, for example in combinatorial chemistry or for the multivalent presentation of ligands. Carbohydrate scaffolds are frequently employed in the synthesis of multivalent glycoconjugates and utilized for the study of fundamental parameters of carbohydrate recognition. However, facile procedures are required to achieve a useful variety of sugar platforms. Here, we report on the synthesis of a series of divalent und tetravalent hydroxypropylated mannosides, using an allylation‐hydroboration sequence. The hydroxypropyl‐linkers were further functionalized with thymine in a Mitsunobu reaction to achieve multivalent glycothymine scaffolds for intramolecular [2+2] photocyclization. This will be of importance to further investigate the influence of the 3D orientation in carbohydrate recognition. We discuss the scope of the allylation‐hydroboration sequence comparing 2,3‐, 2,6‐, and 4,6‐difunctionalization and 2,3,4,6‐tetrafunctionalization of protected 2‐aminoethyl α‐d‐mannopyranosides.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Carbohydrate‐Scaffolded Thymine Multimers: Scope and Limitations of the Allylation–Hydroboration Sequence

Ciuk

Gloe

2018

Eur J Org Chem

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“…via CuAAC or thiol–ene conjugation. , Through variation of the monomer sequence during solid phase assembly, control over the valency (number of ligands), interligand spacing, overall length, and the architecture of the precision macromolecules is realized. Furthermore, different carbohydrate ligands can be combined within one glycomacromolecule giving so-called heteromultivalent structures . Previously, we have introduced two different approaches for the synthesis of heteromultivalent glycomacromolecules: The “building block” approach, shown in Figure A, is based on the stepwise assembly of glycoconjugated building blocks, while the “sequential coupling” approach, shown in Figure B, involves iterative coupling followed by CuAAC conjugation …”

Section: Introductionmentioning

confidence: 99%

Toward Orthogonal Preparation of Sequence-Defined Monodisperse Heteromultivalent Glycomacromolecules on Solid Support Using Staudinger Ligation and Copper-Catalyzed Click Reactions

et al. 2017

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The investigation of heteromultivalent interactions of complex glycoligands and proteins is critical for understanding important biological processes and developing carbohydrate-based pharmaceutics. Synthetic glycomimetics, derived by mimicking complex glycoligands on a variety of scaffolds, have become important tools for studying the role of carbohydrates in chemistry and biology. In this paper, we report on a new synthetic strategy for the preparation of monodisperse, sequence-defined glycooligomers or so-called precision glycomacromolecules based on solid phase oligomer synthesis and the Staudinger ligation. This strategy employs a solid-supported synthetic approach using a novel carboxy-functionalized building block which bears a functional handle required for Staudinger ligation on solid support. Furthermore, we combined Staudinger ligation and copper catalyzed azide alkyne cycloaddition (CuAAC) reactions to synthesize heteromultivalent glycooligomers on solid support for the first time, demonstrating the utility of this approach for the synthesis of heterofunctional glycomacromolecules.

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Glycoclusters and Glycodendrimers

Niedzwiecka

Achebe

Ling

2021

Comprehensive Glycoscience

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Synthesis of AB4-type carbohydrate scaffolds as branching units in the glycosciences

Cited by 6 publications

References 47 publications

Carbohydrate‐Scaffolded Thymine Multimers: Scope and Limitations of the Allylation–Hydroboration Sequence

Carbohydrate‐Scaffolded Thymine Multimers: Scope and Limitations of the Allylation–Hydroboration Sequence

Toward Orthogonal Preparation of Sequence-Defined Monodisperse Heteromultivalent Glycomacromolecules on Solid Support Using Staudinger Ligation and Copper-Catalyzed Click Reactions

Glycoclusters and Glycodendrimers

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