Molecular recognition of surface-immobilized carbohydrates by a synthetic lectin

Rauschenberg, Melanie; Fritz, Eva-Corrina; Schulz, Christian; Kaufmann, Tobias; Ravoo, Bart Jan

doi:10.3762/bjoc.10.138

Cited by 6 publications

(5 citation statements)

References 52 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The result was a series of cis- and trans-poly(norbornene) derived glycopolymers that systematically varied in galactose density (Figure ). Though previous studies indicate that sparsely glycosylated materials more effectively engage their carbohydrate-binding partners, ,, we wished to cover a range of functionalization densities to ensure optimal biological activity. Thus, the panel of glycopolymers varied between 25 and 100% galactose functionalization in 25% increments (Figure ).…”

Section: Resultsmentioning

confidence: 99%

Stereochemical Control Yields Mucin Mimetic Polymers

et al. 2021

View full text Add to dashboard Cite

All animals except sponges produce mucus. Across the animal kingdom, this hydrogel mediates surface wetting, viscosity, and protection against microbes. The primary components of mucus hydrogels are mucinshigh molecular weight O-glycoproteins that adopt extended linear structures. Glycosylation is integral to mucin function, but other characteristics that give rise to their advantageous biological activities are unknown. We postulated that the extended conformation of mucins is critical for their ability to block microbial virulence phenotypes. To test this hypothesis, we developed synthetic mucin mimics that recapitulate the dense display of glycans and morphology of mucin. We varied the catalyst in a ring-opening metathesis polymerization (ROMP) to generate substituted norbornene-derived glycopolymers containing either cis- or trans-alkenes. Conformational analysis of the polymers based on allylic strain suggested that cis- rather than trans-poly(norbornene) glycopolymers would adopt linear structures that mimic mucins. High-resolution atomic force micrographs of our polymers and natively purified Muc2, Muc5AC, and Muc5B mucins revealed that cis-polymers adopt extended, mucin-like structures. The cis-polymers retained this structure in solution and were more water-soluble than their trans-analogs. Consistent with mucin’s linear morphology, cis-glycopolymers were more potent binders of a bacterial virulence factor, cholera toxin. Our findings highlight the importance of the polymer backbone in mucin surrogate design and underscore the significance of the extended mucin backbone for inhibiting virulence.

show abstract

Section: Resultsmentioning

confidence: 99%

Stereochemical Control Yields Mucin Mimetic Polymers

et al. 2021

View full text Add to dashboard Cite

show abstract

“…The authors have cited additional references within the Supporting Information. [61][62][63][64][65]67,68,[68][69][70][71][72][73][74][75][76][77]…”

Section: Supporting Informationmentioning

confidence: 99%

Bioresponsive pseudoGlucosinolates (psGSLs) release Isothiocyanates (ITCs) in the Presence of Nitroreductases

Jimidar,

Ganskow,

Kagho

et al. 2024

Preprint

View full text Add to dashboard Cite

Glucosinolates (GSLs) are secondary metabolites produced as part of an herbivore defence system in plants of the order Brassicales. GSLs release isothiocyanates (ITCs) upon activation by the myrosinase. Beyond their herbivore feeding deterrent properties, these ITCs have multiple interesting bioactivities. However, their release is limited by the presence of myrosinase. Here, we report the concept of pseudoglucosinolates (psGSLs) hijacking the natural release mechanism of GSLs for the release of ITCs and adapting it to nitroreductase as triggering enzymes. We provide the proof-of-concept for nitroreductase-responsive psGSLs and demonstrate their potential for peptide labelling and ITC-prodrug approaches.

show abstract

“…Additional references cited within the supporting information. [26][27][28] Table 2. Conjugation of glucosyl diselenide 7 to various arenes.…”

Section: Supporting Informationmentioning

confidence: 99%

Investigations into the Aqueous Synthesis of Selenoglycoconjugates

Lim

Paradisi

2023

Eur J Org Chem

View full text Add to dashboard Cite

Glycosylation of bioactive molecules has been found to improve the pharmacokinetic properties of the parent molecule. However, their syntheses often require tedious protecting group manipulations. The development of methodologies which allow direct aqueous conversion of unprotected sugars into glycosides is therefore an ambitious goal. Herein, we present a broadly applicable method for the synthesis of selenoglycosides in water. We show the ease of direct conjugation of unprotected glycosyl diselenides with various biomolecules, including resorcinol, resveratrol, and the antitumor agent, gimeracil, furnishing the corresponding selenoglycoconjugates in up to 96 % yield. We also demonstrate the oxidatively‐triggered release of the bioactive drug from the sugar, priming these molecules for medicinal applications. The generality and broad substrate scope of this novel transformation will provide access to various selenium‐containing glycomimetics and glycoconjugates.

show abstract

Molecular recognition of surface-immobilized carbohydrates by a synthetic lectin

Cited by 6 publications

References 52 publications

Stereochemical Control Yields Mucin Mimetic Polymers

Stereochemical Control Yields Mucin Mimetic Polymers

Bioresponsive pseudoGlucosinolates (psGSLs) release Isothiocyanates (ITCs) in the Presence of Nitroreductases

Investigations into the Aqueous Synthesis of Selenoglycoconjugates

Contact Info

Product

Resources

About